Directory of Researchers

OKANO Kentaro
Graduate School of Engineering / Department of Chemical Science and Engineering
Associate Professor
Chemistry
Last Updated :2021/10/24

Researcher Profile and Settings

Affiliation

  • <Faculty / Graduate School / Others>

    Graduate School of Engineering / Department of Chemical Science and Engineering
  • <Related Faculty / Graduate School / Others>

    Faculty of Engineering / Department of Chemical Science and Engineering, Research Center for Membrane and Film Technology

Teaching

  • Faculty of Engineering / Department of Chemical Science and Engineering, 2020, Organic Chemistry Ⅱ
  • Faculty of Engineering / Department of Chemical Science and Engineering, 2020, Organic Chemistry 1
  • Faculty of Engineering / Department of Chemical Science and Engineering, 2020, Instrumental Analytical Chemistry
  • Faculty of Engineering / Department of Chemical Science and Engineering, 2020, Organic Chemistry 3
  • Faculty of Engineering / Department of Chemical Science and Engineering, 2020, Synthetic Organic Chemistry Laboratory
  • Graduate School of Engineering / Department of Chemical Science and Engineering, 2020, Applied Synthetic Organic Chemistry
  • Graduate School of Engineering / Department of Chemical Science and Engineering, 2020, Advanced Organic Reactions B

Research Activities

Research Interests

  • Natural Product Synthesis
  • Synthetic Organic Chemistry

Research Areas

  • Nanotechnology/Materials / Synthetic organic chemistry
  • Life sciences / Pharmaceuticals - chemistry and drug development

Awards

  • Dec. 2016 The Society of Synthetic Organic Chemistry, Incentive Award in Synthetic Organic Chemistry, Japan, 新規合成方法論の開発を基盤とする含窒素高次縮環天然物の全合成

    OKANO KENTARO

    Japan society

  • 2014 Georg Thieme Verlag KG, Thieme Chemistry Journal Award 2015, Awardees are loosely defined as promising young professors at the beginning of their career.

    OKANO KENTARO

    Publisher

  • 2013 天然物化学談話会, 平成25年度 天然物化学談話会 奨励賞, 特異な含窒素縮合環を有する天然有機化合物の合成研究

    OKANO KENTARO

    Japan society

  • 2012 日本薬学会, 平成24年度 日本薬学会東北支部 奨励賞, 芳香族炭素-窒素結合形成法の開発を鍵とする含窒素芳香族天然物の合成研究

    OKANO KENTARO

    Japan society

  • 2011 井上科学振興財団, 第27回 井上研究奨励賞, Enantioselective Total Synthesis of (+)-Yatakemycin Based on CuI-Mediated Aryl Amination

    OKANO KENTARO

    Japan society

  • 2011 Inoue Research Award for Young Scientists

  • 2009 有機合成化学協会, 2009年度 有機合成化学協会 旭化成ファーマ研究企画賞, 配位子による触媒 機能の動的変化を基盤とするワンポット多成分連続反応の開発

    OKANO KENTARO

    Japan society

Published Papers

  • Atsunori Mori, Chihiro Kubota, Keisuke Fujita, Masayasu Hayashi, Tadayuki Ogura, Toyoko Suzuki, Kentaro Okano, Masahiro Funahashi, Masaki Horie

    12 Feb. 2020, Macromolecules, English

    [Refereed]

    Scientific journal

  • Yuto Hioki, Mayu Itoh, Atsunori Mori, Kentaro Okano

    © 2020 Georg Thieme Verlag. All rights reserved. Deprotonative formation of biarylazacyclooctynone (BARAC) from the corresponding enol triflate is described. The reaction furnished the azacyclooctynone within one hour at -78 °C. This process could be performed in one pot from the starting ketone to provide a range of BARAC derivatives in moderate to excellent yields. The protocol enabled the gram-scale formation of the BARAC skeleton by reducing the number of reaction steps. Furthermore, the established method was applied to the synthesis of the BARAC derivative bearing a coumarin moiety.

    2020, Synlett, 31 (2), 189 - 193, English

    [Refereed]

    Scientific journal

  • Atsunori Mori, Masayasu Hayashi, Mitsuru Matsuoka, Shiomi Ashida, Yukiko Ito, Kohei Hosokawa, Toyoko Suzuki, Kentaro Okano, Chi Hsien Wang, Masaki Horie

    © 2020 The Japan Institute of Heterocyclic Chemistry. Nosyl annulation of a bithiophene derivative with nosylamide (NsNH2) gives a 5-7-5 fused N, S-heterocyclic compound. The detailed molecular structure of the obtained nosylamide was analyzed by single-crystal X-ray crystallography. The obtained product was transformed into several amines and amides. The C-Br bond at the fused heterocycle was also subjected to cross-coupling reactions, where the nosyl group was found to be tolerant.

    2020, Heterocycles, 101 (2), 461 - 470, English

    [Refereed][Invited]

    Scientific journal

  • MORI ATSUNORI, ASHIDA SHIOMI, ITO YUKIKO, CHENG JIAQIANG, SUZUKI TOYOKO, OKANO KENTARO, HASHIMOTO TAKAYOSHI

    DFT calculation studies were performed for the estimation of racemization barrier of winding vine-shaped heterobiaryls showing molecular asymmetry. The calculated value showed good agreement compared with that derived from experimental studies. Effects of hetroaromatic structure, carbon-carbon double bond at the winding-vine moiety, substituent at the double bond, and substituent at the heteroaromatic rings were studied.

    PERGAMON-ELSEVIER SCIENCE LTD, Aug. 2019, Heterocycles, 99 (1), 294 - 300, English

    [Refereed]

    Scientific journal

  • SHIBUYA YUSHIN, MIYAGAQA NAOKI, NAKAGAWA NAOKI, SUZUKI TOYOKO, OKANO KENTARO, MORI ATSUNORI

    The unprecedented synthesis of regioregular head-to-tail-type poly(1,4-arylene)s bearing different substituents at the 2- and 5-positions is described. They were prepared by the polymerization of 2,5-disubstituted bromo(chloro)arylenes by selective halogen-metal exchange with a Grignard reagent and subsequent cross-coupling polymerization with a nickel catalyst [NiCl2(dppp)]. Formation of the regioregular poly(1,4-arylene)s were confirmed by NMR spectroscopy, and showed remarkable differences to those polymers having uncontrolled regioregularity. Polymerization of bromo(chloro)arylenes with a chiral alkoxy substituent also led to the regioregular head-to-tail-type polyarylene, which demonstrated circular dichroism, thus suggesting formation of a structure with higher-order regularity.

    Wiley, Jul. 2019, Angewante Chemie International Edition, 58 (28), 9547 - 9550, English

    [Refereed]

    Scientific journal

  • OGURA TADAYUKI, KUBOTA CHIHIRO, SUZUKI TOYOKO, OKANO KENTARO, TANAKA NORIKAZU, MATSUMOTO TAKUYA, NISHINO TAKASHI, MORI ATSUNORI, OKITA TAKUMI, FUNAHASHI MASAHIRO

    Preparation of 2-halo-3-substituted-thiophene bearing a cyclic oligosiloxane moiety in the side chain was carried out and subjected to nickel(II)-catalyzed deprotonative polymerization to give the corresponding polythiophene, which was found to be highly soluble in various organic solvents particularly in hexanes. Treatment of the thin film of the obtained polythiophene with acidic vapor resulted in cross linking of the cyclic siloxane moiety through ring opening. Accompanying doping of the polythiophene main chain on the polymer film indicated improved conductivity with remarkably drastic change in before/after acidic treatment.

    日本化学会, Jun. 2019, Chemistry Letters, 48 (6), 611 - 614, English

    [Refereed]

    Scientific journal

  • T. Satoh, T. Adachi, K. Okano, J. Sakata, H. Tokuyama

    2019, Heterocycles, 99, 310 - 323, English

    [Refereed]

    Scientific journal

  • T. Imaizumi, Y. Yamashita, Y. Nakazawa, K. Okano, J. Sakata, H. Tokuyama

    2019, Organic Letters, 21, English

    [Refereed]

    Scientific journal

  • Ryo Nakura, Kazuki Inoue, Kentaro Okano, Atsunori Mori

    © Georg Thieme Verlag Stuttgart. New York. This study investigated a practical method for regiocontrolled synthesis of precursors of strained cyclohexynes and 1,2-cyclohexadienes, which is a one-pot procedure consisting of a rearrangement of silyl enol ether and subsequent formation of the enol triflates. Triethylsilyl enol ether, derived from cyclohexanone, was treated with a combination of LDA and t -BuOK in n -hexane/THF to encourage the migration of the silyl group to generate an α-silyl enolate. Subsequently, the α-silyl enolate was reacted with Comins' reagent to yield the corresponding enol triflate. Finally, the α-silylated trisubstituted lithium enolate for the synthesis of 1,2-cyclohexadiene precursor was isomerized in the presence of a stoichiometric amount of water for one hour at room temperature to exclusively provide tetrasubstituted lithium enolate for the synthesis of cyclohexyne precursor in one pot.

    2019, Synthesis (Germany), 51 (7), 1561 - 1564

    [Refereed]

    Scientific journal

  • Kentaro Okano, Kazuki Morii, Daichi Mari, Atsunori Mori

    © 2019 The Japan Institute of Heterocyclic Chemistry – A practical synthesis of 4,4-dimethyl-2-oxazolines on pyrrole was achieved via the cyclization of the corresponding amides, which were derived from the trichloroacetylpyrroles. The established conditions were applicable to pyrroles bearing a ketone or an ester moiety. In addition to pyrroles, the method could be extended to the synthesis of the indole derivative.

    2019, Heterocycles, 98 (1), 63 - 77

    [Refereed]

    Scientific journal

  • Kentaro Okano, Yuki Murase, Atsunori Mori

    © 2019 The Japan Institute of Heterocyclic Chemistry. Synthesis of a furan-fused silole and phosphole was achieved through a one-pot halogen dance/homocoupling of a bromofurfural derivative followed by the formation of the silole and phosphole skeleton.

    2019, Heterocycles, 99 (2), 1444 - 1451

    [Refereed]

    Scientific journal

  • ASHIDA SHIOMI, TANAKA NAOKI, ITO YUKIKO, MATSUOKA MITSURU, HASHIMOTO TAKAYOSHI, OKANO KENTARO, MIYAZAKI YUJI, KOBAYASHI TOHRU, YAITA TSUYOSHI, MORI ATSUNORI

    American Chemical Society, Dec. 2018, Journal of Organic Chemistry, 83 (23), 14797–14801, English

    [Refereed]

    Scientific journal

  • Kazuki Maruhashi, Yoichi Okayama, Ryo Inoue, Shiomi Ashida, Yuka Toyomori, Kentaro Okano, Atsunori Mori

    The chirality of winding vine-shaped heterobiaryls with molecular asymmetry is recognized by a sugar-based chiral oxidant. Kinetic resolution of (±)-bisbenzoimidazole bearing an olefin moiety takes place with Shi's asymmetric epoxidation to observe k rel value up to ca. 35 affording the corresponding epoxide. The reaction of a (±)-bithiophene derivative also recognized the chirality to give the corresponding epoxide with er of 96:4 at 39% conversion. Dynamic kinetic resolution is found to take place when unsymmetrical biaryl composed of benzoimidazole/thiophene is subjected to Shi's epoxidation, whose conversion of the racemic substrate exceeds to 50%.

    Nature Publishing Group, 01 Dec. 2018, Scientific Reports, 8 (1), English

    [Refereed]

    Scientific journal

  • Mari Daichi, Miyagawa Naoki, Okano Kentaro, Mori Atsunori

    16 Nov. 2018, JOURNAL OF ORGANIC CHEMISTRY, 83 (22), 14126 - 14137

    [Refereed]

  • Inoue Ryo, Yamaguchi Mana, Murakami Yoshiaki, Okano Kentaro, Mori Atsunori

    Oct. 2018, ACS OMEGA, 3 (10), 12703 - 12706

    [Refereed]

  • Itabashi Suguru, Shimomura Masashi, Sato Manabu, Azuma Hiroki, Okano Kentaro, Sakata Juri, Tokuyama Hidetoshi

    Aug. 2018, SYNLETT, 29 (13), 1786 - 1790

    [Refereed]

  • Naoki Miyagawa, Toyoko Suzuki, Kentaro Okano, Takuya Matsumoto, Takashi Nishino, Atsunori Mori

    Polyamide composed of furan dimer, which is prepared from biomass-derived organic molecule 2-furfural, is synthesized. The reaction of 2,2′-furan dimer 5,5′-dicarbonyl chloride with several 1,ω-diamines was carried out with a solution or interfacial polycondensation leading to the corresponding polyamide. Measurement of the melting point was performed resulting to exhibit a higher temperature compared with the related polyamide bearing a single furan ring composed of furan-2,5-dicarboxylic acid (FDCA). Thermal analyses (TG–DTA) also indicated higher temperatures of decomposition than those of FDCA-derived polyamide. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 1516–1519.

    John Wiley and Sons Inc., 15 Jul. 2018, Journal of Polymer Science, Part A: Polymer Chemistry, 56 (14), 1516 - 1519, English

    [Refereed]

    Scientific journal

  • Inoue Kazuki, Nakura Ryo, Okano Kentaro, Mori Atsunori

    06 Jul. 2018, EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, (25), 3343 - 3347

    [Refereed]

  • Hioki Yuto, Yukioka Taro, Okano Kentaro, Mori Atsunori

    Jul. 2018, ASIAN JOURNAL OF ORGANIC CHEMISTRY, 7 (7), 1298 - 1301

    [Refereed]

  • Seiichi Uchiyama, Toshikazu Tsuji, Kyoko Kawamoto, Kentaro Okano, Eiko Fukatsu, Takahiro Noro, Kumiko Ikado, Sayuri Yamada, Yuka Shibata, Teruyuki Hayashi, Noriko Inada, Masaru Kato, Hideki Koizumi, Hidetoshi Tokuyama

    A cationic fluorescent nanogel thermometer based on thermo-responsive N-isopropylacrylamide and environment-sensitive benzothiadiazole was developed with a new azo compound bearing imidazolium rings as the first cationic radical initiator. This cationic fluorescent nanogel thermometer showed an excellent ability to enter live mammalian cells in a short incubation period (10 min), a high sensitivity to temperature variations in live cells (temperature resolution of 0.02–0.84 °C in the range 20–40 °C), and remarkable non-cytotoxicity, which permitted ordinary cell proliferation and even differentiation of primary cultured cells.

    Wiley-VCH Verlag, 04 May 2018, Angewandte Chemie - International Edition, 57 (19), 5413 - 5417, English

    [Refereed]

    Scientific journal

  • Yoshiki Yamane, Kazuhiro Sunahara, Kentaro Okano, Atsunori Mori

    A magnesium bisamide-mediated halogen dance of bromothiophenes is described. The thienylmagnesium species generated in situ is more stable than the corresponding thienyllithium species, which was applied to trap the transient anion species with several electrophiles, such as allyl iodide, phenyl isocyanate, and tributylstannyl chloride. The utility of the magnesium bisamide-mediated halogen dance is useful in the concise synthesis of a medicinally advantageous compound via a one-pot, ester-directed halogen dance/Negishi cross coupling.

    American Chemical Society, 16 Mar. 2018, Organic Letters, 20 (6), 1688 - 1691, English

    [Refereed]

    Scientific journal

  • Naoya Miyamoto, Yuki Nakazawa, Takanori Nakamura, Kentaro Okano, Sota Sato, Zhe Sun, Hiroyuki Isobe, Hidetoshi Tokuyama

    A new synthetic route to functionalized 9,10-diarylanthracenes has been developed. 9,10-Epoxyanthracene intermediates were prepared by [4+2] cycloaddition of 1,3-diarylisobenzofuran with a variety of functionalized benzyne intermediates, which were obtained by Mg(TMP) 2 ·2LiCl-mediated benzyne generation. For the cleavage of the resultant 9,10-epoxyanthracene intermediates, we developed mild deoxygenation conditions using a combination of trifluoroacetic acid and Et 3 SiH. The utility of this sequence was demonstrated by application to the synthesis of 5,7,12,14-tetraphenylpentacene.

    Georg Thieme Verlag, 01 Mar. 2018, Synlett, 29 (4), 513 - 518, English

    [Refereed]

    Scientific journal

  • Yuki Hayashi, Kentaro Okano, Atsunori Mori

    A two-pot synthesis of thieno[3,2-b]indole from 2,5-dibromothiophene is described. A halogen dance of 2,5-dibromothiophene was performed with LDA, and subsequent Negishi coupling was performed with 2-iodoaniline derivatives to provide the corresponding coupling products. The resulting two bromo groups have different reactivities, which were utilized for the one-pot Suzuki-Miyaura coupling/intramolecular Buchwald-Hartwig amination to produce thieno[3,2-b]indole via an assisted tandem catalysis that involved in situ ligand exchange.

    American Chemical Society, 16 Feb. 2018, Organic Letters, 20 (4), 958 - 961, English

    [Refereed]

    Scientific journal

  • Kentaro Okano, Yuki Murase, Naoki Miyagawa, Kana Ashida, Atsunori Mori

    2018, Heterocycles, 97, 580 - 590, English

    [Refereed]

    Scientific journal

  • Naoki Miyagawa, Yuki Murase, Kentaro Okano, Atsunori Mori

    A halogen dance of a benzoxazole-conjugated bromofuran derived from furfural is described. The reaction proceeds through a benzoxazole-directed lithiation to provide the a-lithiofuran, which is subjected to Negishi coupling to give a-arylated benzoxazole-conjugated furan derivatives. The synthetic utility of the reaction was demonstrated by transformation of the residual bromo group into a side chain bearing a siloxane moiety, which resulted in a significant improvement in solubility in organic solvents.

    GEORG THIEME VERLAG KG, Jun. 2017, SYNLETT, 28 (9), 1106 - 1110, English

    [Refereed]

    Scientific journal

  • Kana Ashida, Yuki Murase, Naoki Miyagawa, Kentaro Okano, Atsunori Mori

    Effective transformation of a biomass-derived heteroaromatic compound furfural into conjugated polymer is described. Furylthiazole composed of furan and thiazole rings is employed as a monomer and palladium-catalyzed C-H coupling polycondensation furnishes the corresponding formal alternating copolymer. The coupling reaction in the presence of Pd(OAc)(2) (20mol%) as a catalyst undergoes polymerization in >99% yield with M-n = 10.2 x 10(3).

    CHEMICAL SOC JAPAN, May 2017, BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 90 (5), 565 - 567, English

    [Refereed]

    Scientific journal

  • Naoki Nakagawa, Tadayuki Ogura, Keisuke Fujita, Yugo Sumino, Takayoshi Hashimoto, Kentaro Okano, Atsunori Mori

    A simple and ubiquitous nickel(II) complex NiCl2(PPh3)(2) catalyzes polymerization of oligothiophenes. Treatment of chlorobithiophene with chloromagnesium 2,2,6,6-tetramethyl-piperidin-1-yl lithium chloride salt (TMPMgCl center dot LiCl) followed by addition of 2.0 mol% NiCl2(PPh3)(2) undergoes deprotonative polymerization leading to poly(3-hexylthiophene) (P3HT) with M-n = 13000 and M-w/M-n = 1.67 (74% yield). The related terthiophene and quaterthiophene also polymerize to afford the corresponding polythiophene while little polymerization takes place with 2-chloro-3-hexylthiophene under similar conditions.

    CHEMICAL SOC JAPAN, Apr. 2017, CHEMISTRY LETTERS, 46 (4), 453 - 455, English

    [Refereed]

    Scientific journal

  • Keisuke Fujita, Naoki Nakagawa, Kazuhiro Sunahara, Tadayuki Ogura, Kentaro Okano, Atsunori Mori

    Deprotonative metalation of 2-chloro-3-substituted thiophene at the 5-position of the thiophene ring is performed by using a bulky magnesium amide 2,2,6,6-tetramethylpiperidin-1-yl magnesium chloride lithium chloride salt (TMPMgCl.LiCl). The obtained metallic species reacts with bromothiophene to afford the regioregular headto- tail-type chlorobithiophene, which is subjected to further end functionalization by the coupling reaction with the C-Cl bond. Deprotonative C-H coupling polycondensation of substituted chlorobithiophene derivatives gives polythiophene as a formal alternating copolymer.

    GEORG THIEME VERLAG KG, Mar. 2017, SYNTHESIS-STUTTGART, 49 (6), 1285 - 1294, English

    [Refereed]

    Scientific journal

  • Yuto Hioki, Kentaro Okano, Atsunori Mori

    Deprotonative generation of cyclohexynes, cycloheptynes, and cyclooctynes was achieved by controlling the reactivities of transient anionic species from the corresponding enol triflates with magnesium bis(2,2,6,6-tetramethylpiperidide) as a base. The starting enol triflates are readily obtained through triflation of the corresponding ketones, allowing direct access to the cycloalkynes.

    ROYAL SOC CHEMISTRY, Feb. 2017, CHEMICAL COMMUNICATIONS, 53 (17), 2614 - 2617, English

    [Refereed]

    Scientific journal

  • Naoki Miyagawa, Tadayuki Ogura, Kentaro Okano, Takuya Matsumoto, Takashi Nishino, Atsunori Mori

    Furan dimer diester was obtained by reductive or oxidative homocoupling of furan carboxylate derivatives in the presence of a nickel or palladium catalyst. Treatment of the obtained diester with 1,ω-diol in the presence of titanium alkoxide as a catalyst leads to the corresponding polyester in excellent yields. The obtained polymers show remarkably high melting points compared with the related polyesters composed of a single furan ring derived from furan-2,5-dicarboxylic acid (FDCA). Thermal properties of the furan dimer-derived polyesters are comparable with those of terephthalate polymers such as poly(ethylene terephthalate).

    Chemical Society of Japan, 2017, Chemistry Letters, 46 (10), 1535 - 1538, English

    [Refereed]

    Scientific journal

  • Manabu Sato, Hiroki Azuma, Akihiro Daigaku, Sota Sato, Kiyosei Takasu, Kentaro Okano, Hidetoshi Tokuyama

    Stereoselective total syntheses of (-)-histrionicotoxin and (-)-histrionicotoxin 235A are described. The 1-azaspiro[5.5]undecane skeleton was constructed diastereoselectively by a radical translocation-cyclization reaction involving a chiral cyclic acetal; the use of tris( trimethylsilyl) silane was crucial for the high diastereoselectivity. The cyclization product was converted into (-)-histrionicotoxin 235A through a one-pot partial-reduction-allylation reaction of a derivative containing an unprotected lactam. Finally, two terminal alkenes were transformed into enynes with the 1,3-amino alcohol protected as an oxathiazolidine oxide to complete the total synthesis of (-)-histrionicotoxin.

    WILEY-V C H VERLAG GMBH, Jan. 2017, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 56 (4), 1087 - 1091, English

    [Refereed]

    Scientific journal

  • Atsunori Mori, Daichi Matsuoka, Shiomi Ashida, Ryo Inoue, Kazuki Maruhashi, Yoichi Okayama, Guan Hong Jin, Kentaro Okano

    Oxidative condensation of N-(3-buten-1-yl)-1,2-phenylenediamine with a formylated heteroarene bearing 3-buten-1-yl substituent gives unsymmetrical heterobiaryl in 42-86% yields. Ring-closing metathesis of the thus obtained product affords the cyclized product, which resulted in separation of each enantiomer by HPLC with a chiral column showing molecular asymmetry.

    PERGAMON-ELSEVIER SCIENCE LTD, Jan. 2017, HETEROCYCLES, 95 (1), 268 - 276, English

    [Refereed]

    Scientific journal

  • Hidetoshi Tokuyama, Kaori Yamada, Hideto Fujiwara, Juri Sakata, Kentaro Okano, Malipan Sappan, Masahiko Isaka

    The structure of a C-2-syminetric epidithiodike-topiperazine alkaloid, SCH 64874, was determined by semisynthesis. The relative stereochemistry of the beta-hydroxy carboxylic acid chain having, three chiral centers was determined by comparison of the NMR data of the four possible diastereomeric beta-hydroxy carboxylic acid fragments with those of SCH 64874. Condensation of the (-)-deacetylaranotin core with two enantiomeric beta-hydroxy carboxylic acids revealed the relative stereochemistry of SCH 64874. The relative stereochemistry of the beta-keto carboxylic acid chain of the analogous alkaloid hirsutellomycin was determined in a stepwise manner. The C4'-C6' syn relationships were predicted by comparing the NMR data of the corresponding ester fragments with that of hirsutellomycin. The relative stereochemistry of the whole molecule, including the epimerizable C2' stereoeenter, was determined by introduction of four possible side chains into the bisdethiodi(methylthio)deacetylaranotin core. We found that the stereochemistry of CZ' converged with that of the thermodynamically stable form influenced by the core structure.

    AMER CHEMICAL SOC, Jan. 2017, JOURNAL OF ORGANIC CHEMISTRY, 82 (1), 353 - 371, English

    [Refereed]

    Scientific journal

  • Atsunori Mori, Daichi Matsuoka, Shiomi Ashida, Ryo Inoue, Kazuki Maruhashi, Yoichi Okayama, Guan Hong Jin, Kentaro Okano

    Oxidative condensation of N-(3-buten-1-yl)-1,2-phenylenediamine with a formylated heteroarene bearing 3-buten-1-yl substituent gives unsymmetrical heterobiaryl in 42-86% yields. Ring-closing metathesis of the thus obtained product affords the cyclized product, which resulted in separation of each enantiomer by HPLC with a chiral column showing molecular asymmetry.

    PERGAMON-ELSEVIER SCIENCE LTD, Jan. 2017, HETEROCYCLES, 95 (1), 268 - 276, English

    [Refereed]

    Scientific journal

  • Kentaro Okano, Kazuhiro Sunahara, Yoshiki Yamane, Yuki Hayashi, Atsunori Mori

    One-pot halogen dance/Negishi cross-coupling of readily available 2,5-dibromothiophenes is described. A lithium diisopropylamide (LDA)-mediated halogen dance reaction resulted in the formation of thermodynamically stable -lithiodibromothiophenes, which were transmetalated with ZnCl2 and subjected to Negishi cross-coupling to provide the corresponding arylated dibromothiophenes in one pot. The resultant -bromo group was much less reactive than the remaining -bromo group, which was used in a one-pot double Suzuki-Miyaura cross-coupling, enabling facile synthesis of multiply arylated thiophenes.

    WILEY-V C H VERLAG GMBH, Nov. 2016, CHEMISTRY-A EUROPEAN JOURNAL, 22 (46), 16450 - 16454, English

    [Refereed]

    Scientific journal

  • Yuki Murase, Kana Ashida, Shota Tanaka, Kentaro Okano, Atsunori Mori

    Synthesis of furyloxazole was performed from biomass-derived furfural and senile methyl ester through dehydrative condensation and oxidation in one pot. Bromination and subsequent palladium-catalyzed arylation with arylboronates proceeded smoothly at the furan ring to provide arylated furylthiazoles. Arylation of C-H bond at the 5 position of the oxazole ring under Fagnou's conditions led to formation of diarylated furyloxazoles, which exhibit higher quantum yields over those of the related furylthiazole derivatives.

    PERGAMON-ELSEVIER SCIENCE LTD, Apr. 2016, HETEROCYCLES, 93 (1), 140 - 149, English

    [Refereed]

    Scientific journal

  • Kosuke Fujioka, Naoya Miyamoto, Hiroki Toya, Kentaro Okano, Hidetoshi Tokuyama

    Synthetic studies on acochlearine are described. The pentacyclic A/B/C/E/F ring system of acochlearine was constructed from a bicyclic enone via chemoselective reductive amination, one-pot bromination-intramolecular Mannich reaction cascade, and 6-electrocyclization.

    GEORG THIEME VERLAG KG, Mar. 2016, SYNLETT, 27 (4), 621 - 625, English

    [Refereed]

    Scientific journal

  • Shun Okaya, Keiichiro Okuyama, Kentaro Okano, Hidetoshi Tokuyama

    Wiley Blackwell, 2016, Organic Syntheses, 93, 63 - 74, English

    [Refereed]

    Scientific journal

  • Taichi Kurogi, Shun Okaya, Hideto Fujiwara, Kentaro Okano, Hidetoshi Tokuyama

    The first total synthesis of an epidithiodiketopiperazine alkaloid, (+)-MPC1001B, was accomplished. This synthesis features a tetra-n-butylammonium fluoride mediated intramolecular aldol reaction for forming the 15-membered macrolactone ring, and the construction of an epidithiodiketopiperazine substructure through a stepwise sulfenylation reaction involving a novel trityl trisulfide (TrSSS)-group transfer.

    WILEY-V C H VERLAG GMBH, Jan. 2016, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 55 (1), 283 - 287, English

    [Refereed]

    Scientific journal

  • DIBALH-Mediated Reductive Ring-Expansion Reaction of Cyclic Ketoxime

    IMAIZUMI Taku, OKANO Kentaro, TOKUYAMA Hidetoshi

    2016, Org. Synth., 93, 1 - 13, English

    [Refereed]

    Scientific journal

  • Toshiharu Noji, Kentaro Okano, Hidetoshi Tokuyama

    One-pot synthesis of tryptophanol derivative from N-Boc-aziridine and indole has been developed. The ring opening reaction of the aziridine takes place smoothly at -30 degrees C in a regioselective manner and tolerates a wide range of functional groups including halogens attached to the aromatic ring, which was also performed on a gram scale. The resulting tryptophanol derivative was converted to (-)-indolactam V from commercially available 4-bromoindole through a copper-mediated aryl amination in nine steps with an overall yield of 32%. (C) 2015 Elsevier Ltd. All rights reserved.

    PERGAMON-ELSEVIER SCIENCE LTD, Jun. 2015, TETRAHEDRON, 71 (23), 3833 - 3837, English

    [Refereed]

    Scientific journal

  • Yu Yoshii, Takanori Otsu, Norihiko Hosokawa, Kiyosei Takasu, Kentaro Okano, Hidetoshi Tokuyama

    Enantiocontrolled construction of B-E rings of penitrem E was accomplished from 4-iodoindole in 13 steps with an overall yield of 1.7%. Diastereoselective Tf2NH-catalyzed (2+2)-cycloaddition between silyl enol ether and methyl acrylate furnished a tetracyclic product possessing the characteristic cyclobutane ring bearing a hydroxyl group.

    ROYAL SOC CHEMISTRY, 2015, CHEMICAL COMMUNICATIONS, 51 (6), 1070 - 1073, English

    [Refereed]

    Scientific journal

  • Kentaro Okano, Shun Okaya, Taichi Kurogi, Hideto Fujiwara, Hidetoshi Tokuyama

    The steric effect of vinylogous Rubottom oxidation of proline-fused cyclohexadienol silyl ether was investigated. The facial selectivity in the oxidation is governed by a synergistic effect of the proximal ester and a protective group on the nitrogen.

    PERGAMON-ELSEVIER SCIENCE LTD, Jan. 2015, HETEROCYCLES, 90 (2), 1299 - 1308, English

    [Refereed]

    Scientific journal

  • Yuichi Momoi, Kei-ichiro Okuyama, Hiroki Toya, Kenji Sugimoto, Kentaro Okano, Hidetoshi Tokuyama

    The enantiocontrolled total synthesis of (-)-haouamine B pentaacetate was accomplished via an optically active indane-fused beta-lactam, which was prepared by a newly developed Friedel-Crafts reaction. Subsequent cleavage of the beta-lactam and an intramolecular McMurry coupling reaction provided the core indane-fused tetrahydropyridine, which led to the elucidation of the structure, as proposed by Trauner and Zubia.

    WILEY-V C H VERLAG GMBH, Nov. 2014, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 53 (48), 13215 - 13219, English

    [Refereed]

    Scientific journal

  • Hiroki Toya, Takahito Satoh, Kentaro Okano, Kiyosei Takasu, Masataka Ihara, Atsushi Takahashi, Haruo Tanaka, Hidetoshi Tokuyama

    Total synthesis of (-)- and (+)-petrosin was accomplished. Stereocontrolled construction of the quinolizidine ring was achieved through a diastereoselective Mannich reaction and an aza-Michael reaction. Head-to-tail dimerization was performed by assembly of the two monomers using Suzuki-Miyaura cross coupling and subsequent ring-closing metathesis to construct the 16-membered ring. Biological evaluation of synthetic (-)- and (+)-petrosin and its derivatives indicated that the bispiperidine structure was necessary for the inhibition of syncytium formation. (C) 2014 Elsevier Ltd. All rights reserved.

    PERGAMON-ELSEVIER SCIENCE LTD, Oct. 2014, TETRAHEDRON, 70 (43), 8129 - 8141, English

    [Refereed]

    Scientific journal

  • Yuichi Momoi, Kentaro Okano, Hidetoshi Tokuyama

    A mild and straightforward synthesis of biaryls is described that is performed through direct arylation of the C-H bond of (arene) Cr(CO)(3) upon deprotonation with Mg(2,2,6,6-tetramethylpiperazide)(2)center dot 2LiCl and subsequent palladium-catalyzed cross-coupling reaction.

    GEORG THIEME VERLAG KG, Oct. 2014, SYNLETT, 25 (17), 2503 - 2507, English

    [Refereed]

    Scientific journal

  • Hidetsura Cho, Yusuke Iwama, Kentaro Okano, Hidetoshi Tokuyama

    Synthesis of three clinical candidates for medicines, a human urate transporter-1 inhibitor, an arginine vasopressin antagonist, and a 17 beta-hydroxysteroid dehydrogenase type-3 inhibitor, is described. These compounds were synthesized via construction of their 3,4-dihydro-2H-benzo[b][1,4]oxazine, dibenzodiazepine, and dibenzazocine skeletons, respectively, using the reductive ring-expansion reaction of the corresponding bicyclic or tricyclic oximes with diisobutylaluminum hydride.

    PHARMACEUTICAL SOC JAPAN, Apr. 2014, CHEMICAL & PHARMACEUTICAL BULLETIN, 62 (4), 354 - 363, English

    [Refereed]

    Scientific journal

  • Yusuke Iwama, Takahiro Noro, Kentaro Okano, Hidetsura Cho, Hidetoshi Tokuyama

    Synthesis of xanthone oxime and related compounds via nitrosation of the dibenzylic position using a combination of tert-butyl nitrite and potassium hexamethyldisilazide is described. The reaction conditions are effective for the synthesis of xanthone oxime as well as thioxanthone, acridone, and anthrone oximes, which have been difficult to synthesize from the corresponding ketones by conventional dehydrative condensation with hydroxylamine.

    PERGAMON-ELSEVIER SCIENCE LTD, Jan. 2014, HETEROCYCLES, 88 (2), 1433 - 1444, English

    [Refereed]

    Scientific journal

  • Kentaro Okano, Nakako Mitsuhashi, Hidetoshi Tokuyama

    A concise total synthesis of PDE-I and -II featuring copper-mediated double aryl amination with the combination of CuI, CsOAc, and Cs2CO 3 is described. The highly substituted pyrroloindole skeleton was constructed by a one-pot five-step sequence including double aryl amination, β-elimination, deprotection of a Cbz group, and unexpected formation of an indole via removal of an Ns group followed by rearomatization. The undesired elimination of the protecting group (Ns group) was hampered by using the Boc group as a protecting group in the second-generation synthesis, which excluded the reduction of the indole required in the first-generation synthesis. © 2013 Elsevier Ltd. All rights reserved.

    23 Dec. 2013, Tetrahedron, 69 (51), 10946 - 10954, English

    [Refereed]

    Scientific journal

  • Takahiro Noro, Kentaro Okano, Hidetoshi Tokuyama

    A formal synthesis of a hepatitis C virus (HCV) inhibitor is described. The synthesis features a benzyne-mediated one-pot indoline formation-methylation sequence and an In(OTf)(3)-mediated mild oxa-Pictet-Spengler reaction for the synthesis of substituted electron-rich pyranoindole.

    GEORG THIEME VERLAG KG, Oct. 2013, SYNLETT, 24 (16), 2143 - 2147, English

    [Refereed]

    Scientific journal

  • Yusuke Iwama, Kentaro Okano, Kenji Sugimoto, Hidetoshi Tokuyama

    A racemic synthesis of mersicarpine (1) was achieved by the Mizoroki-Heck reaction and a DIBALH-mediated reductive ring-expansion reaction. Based on a first-generation synthesis, a second-generation enantiocontrolled total synthesis of (-)-mersicarpine (1) was achieved by an 8-pot/11-step sequence in 21% overall yield from commercially available 2-ethylcyclohexanone. Subjection of a ketoester, which was prepared by an asymmetric Michael addition (according to the protocol by d'Angelo and Desmaele), and phenylhydrazine to modified Fischer indole conditions provided a six-membered tricyclic indole. Benzylic oxidation and subsequent oxime formation provided a ketoxime, which was treated with diisobutylaluminum hydride (DIBALH) to construct the characteristic azepinoindole skeleton in good yield. In the DIBALH-mediated reductive ring-expansion reaction, gradually increasing the reaction temperature and in situ-protection of the nitrogen in an oxygen-sensitive azepinoindole with a benzyloxycarbonyl (Cbz) group were crucial for the high-yielding process. With these methodologies, the short-step and efficient synthesis of (-)-mersicarpine was accomplished. Several synthetic efforts are also described.

    WILEY-V C H VERLAG GMBH, Jul. 2013, CHEMISTRY-A EUROPEAN JOURNAL, 19 (28), 9325 - 9334, English

    [Refereed]

    Scientific journal

  • Toshiharu Noji, Hideto Fujiwara, Kentaro Okano, Hidetoshi Tokuyama

    A benzyne-mediated synthesis of substituted indolines and carbazoles was developed. The reaction includes generation of benzyne using Mg(TMP)(2)center dot 2LiCl as a base, cyclization, and trapping the resulting organomagnesium intermediate with an electrophile to provide a series of substituted indolines and carbazoles in a regiospecific manner. This was applied to a concise five-pot total synthesis of heptaphylline.

    AMER CHEMICAL SOC, Apr. 2013, ORGANIC LETTERS, 15 (8), 1946 - 1949, English

    [Refereed]

    Scientific journal

  • Hidetsura Cho, Yusuke Iwama, Kentaro Okano, Hidetoshi Tokuyama

    Synthetic studies on a 17 beta-hydroxysteroid dehydrogenase type 3 (17 beta-HSD3) inhibitor are described. The unsymmetrical dibenzazocine skeleton was constructed by a regiocontrolled ring-expansion reaction of a cyclic oxime with DIBAL-H.

    GEORG THIEME VERLAG KG, Apr. 2013, SYNLETT, 24 (7), 813 - 816, English

    Scientific journal

  • Takashi Oshiyama, Takahito Satoh, Kentaro Okano, Hidetoshi Tokuyama

    Total synthesis of pyrroloquinoline alkaloids, such as makaluvamine AID, damirone B, batzelline C, makaluvone, and isobatzelline C, was achieved featuring a one-pot benzyne-mediated cyclization-functionalization reaction. The synthetic utility was demonstrated by the construction of the common pyrrolo[4,3,2-de]quinoline skeleton. (C) 2012 Elsevier Ltd. All rights reserved.

    PERGAMON-ELSEVIER SCIENCE LTD, Nov. 2012, TETRAHEDRON, 68 (46), 9376 - 9383, English

    Scientific journal

  • Hidetsura Cho, Yusuke Iwama, Nakako Mitsuhashi, Kenji Sugimoto, Kentaro Okano, Hidetoshi Tokuyama

    The ring-expansion reactions of heterocyclic ketoximes and carbocyclic ketoximes with several reductants such as AlHCl2, AlH3 (alane), LiAlH4, LiAlH((OBu)-Bu-t)(3), and (MeOCH2CH2O)(2)AlH2Na (Red-Al) were examined. Among reductants, AlHCl2 (LiAlH4:AlCl3 = 1:3) in cyclopentyl methyl ether (CPME) has been found to be a suitable reagent for the reaction, and the rearranged cyclic secondary amines were obtained in good to excellent yields.

    MDPI AG, Jun. 2012, MOLECULES, 17 (6), 7348 - 7355, English

    Scientific journal

  • Yusuke Iwama, Kentaro Okano, Kenji Sugimoto, Hidetoshi Tokuyama

    A concise total synthesis of (-)-mersicarpine from a known cyclohexanone was accomplished. The azepinoindole core was constructed by a DIBAL-H-mediated reductive ring-expansion reaction of oxime.

    AMER CHEMICAL SOC, May 2012, ORGANIC LETTERS, 14 (9), 2320 - 2322, English

    [Refereed]

    Scientific journal

  • Takashi Oshiyama, Takahito Satoh, Kentaro Okano, Hidetoshi Tokuyama

    The total synthesis of batzelline C and isobatzelline C was accomplished. The synthesis features the construction of the highly substituted pyrrolo[4,3,2-de] quinoline skeleton by a benzyne-mediated cyclization- functionalization sequence.

    ROYAL SOC CHEMISTRY, 2012, RSC ADVANCES, 2 (12), 5147 - 5149, English

    [Refereed]

    Scientific journal

  • Hideto Fujiwara, Taichi Kurogi, Shun Okaya, Kentaro Okano, Hidetoshi Tokuyama

    WILEY-V C H VERLAG GMBH, 2012, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 51 (52), 13062 - 13065, English

    [Refereed]

    Scientific journal

  • Kentaro Okano, Yu Yoshii, Hidetoshi Tokuyama

    The common pentacyclic skeleton of indole diterpene alkaloids, paspaline and its derivatives was constructed by a sequential reaction. The appropriate choice of the protecting group on the indole nitrogen was critical for the formation of bis(methylthio)allylic alcohol, which then underwent sulfonium ion formation and intramolecular electrophilic C-C-bond formation at the indole 3-position.

    PERGAMON-ELSEVIER SCIENCE LTD, Jan. 2012, HETEROCYCLES, 84 (2), 1325 - 1334, English

    Scientific journal

  • Hiroki Azuma, Kentaro Okano, Hidetoshi Tokuyama

    An acylsilane synthesis by a Pd-catalyzed cross-coupling reaction of thiol esters and silylzinc chlorides was developed. S-Phenyl thiol esters with a variety of functional groups were converted to corresponding acylsilanes.

    CHEMICAL SOC JAPAN, Sep. 2011, CHEMISTRY LETTERS, 40 (9), 959 - 961, English

    [Refereed]

    Scientific journal

  • Hiroki Azuma, Kentaro Okano, Tohru Fukuyama, Hidetoshi Tokuyama

    Wiley Blackwell, 01 Jul. 2011, Organic Syntheses, 88, 152 - 161, English

    [Refereed]

    Scientific journal

  • Toshiharu Noji, Kentaro Okano, Tohru Fukuyama, Hidetoshi Tokuyama

    Wiley Blackwell, 01 Jul. 2011, Organic Syntheses, 88, 388 - 397, English

    [Refereed]

    Scientific journal

  • Hidetsura Cho, Kenji Sugimoto, Yusuke Iwama, Nakako Mitsuhashi, Kentaro Okano, Hidetoshi Tokuyama

    A systematic investigation of a reductive ring-expansion reaction of N-monosubstituted hydroxylamines with diisobutylaluminum hydride (DIBALH) was carried out. The reaction regiospecifically provided a variety of bicyclic or tricyclic heterocycles or linear secondary amines containing nitrogen attached to an aromatic ring.

    PERGAMON-ELSEVIER SCIENCE LTD, Mar. 2011, HETEROCYCLES, 82 (2), 1633 - +, English

    Scientific journal

  • Hidetoshi Tokuyama, Kentaro Okano, Hideto Fujiwara, Toshiharu Noji, Tohru Fukuyama

    A highly efficient total synthesis of dictyodendrins A-E was accomplished. The synthesis features a novel benzyne-mediated one-pot indoline formation/cross-coupling sequence for the construction of a highly substituted key indoline intermediate. Peripheral substituents were introduced onto this intermediate in a modular fashion to complete the total synthesis of dictyodendrins A-E.

    WILEY-V C H VERLAG GMBH, Feb. 2011, CHEMISTRY-AN ASIAN JOURNAL, 6 (2), 560 - 572, English

    [Refereed]

    Scientific journal

  • Kei-ichiro Okuyama, Yuichi Momoi, Kenji Sugimoto, Kentaro Okano, Hidetoshi Tokuyama

    Synthetic studies on haouamine B are described. The characteristic indenotetrahydropyridone skeleton was constructed by intramolecular Friedel-Crafts alkylation of mesyloxy beta-lactam derivative and intramolecular McMurry coupling as key processes.

    GEORG THIEME VERLAG KG, Jan. 2011, SYNLETT, 2011 (1), 73 - 76, English

    Scientific journal

  • Hiroki Toya, Kentaro Okano, Kiyosei Takasu, Masataka Ihara, Atsushi Takahashi, Haruo Tanaka, Hidetoshi Tokuyama

    The enantioselective total synthesis of (-)- and (+)-petrosin is described. The union of two key segments was executed by Suzuki Miyaura coupling. The quinolizidine rings were stereoselectively constructed via a diastereoselective Mannich reaction and an aza-Michael reaction. The 16-membered ring was constructed by ring-closing metathesis with the second-generation Grubbs catalyst.

    AMER CHEMICAL SOC, Nov. 2010, ORGANIC LETTERS, 12 (22), 5196 - 5199, English

    [Refereed]

    Scientific journal

  • Manabu Fujitani, Masami Tsuchiya, Kentaro Okano, Kiyosei Takasu, Masataka Ihara, Hidetoshi Tokuyama

    A total synthesis of (+/-)-lepadiformine A was accomplished through construction of the 1-azaspiro[4.5]decane skeleton by a sequential radical translocation-cyclization reaction.

    GEORG THIEME VERLAG KG, Mar. 2010, SYNLETT, (5), 822 - 826, English

    Scientific journal

  • Kentaro Okano, Nakako Mitsuhashi, Hidetoshi Tokuyama

    A concise total synthesis of PDE-II featuring copper-mediated double aryl amination with the combination of CuI, CsOAc, and Cs(2)CO(3) is described. The highly substituted pyrroloindole skeleton was constructed by a one-pot five-step sequence including double aryl amination, beta-elimination, deprotection of a Cbz group, and removal of an Ns group followed by rearomatization.

    ROYAL SOC CHEMISTRY, 2010, CHEMICAL COMMUNICATIONS, 46 (15), 2641 - 2643, English

    [Refereed]

    Scientific journal

  • Kentaro Okano, Hideto Fujiwara, Toshiharu Noji, Tohru Fukuyama, Hidetoshi Tokuyama

    WILEY-BLACKWELL, 2010, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 49 (34), 5925 - 5929, English

    [Refereed]

    Scientific journal

  • ヨウ化銅を用いる芳香族アミノ化反応を基盤とした(+)-ヤタケマイシンの不斉全合成

    OKANO KENTARO

    Mar. 2009, 東京大学学位論文, English

    Doctoral thesis

  • Protection of Diols with p-(tert-Butyldimethylsilyloxy)benzylidene Acetal and Its Deprotection: (4-((4R,5R)-4,5-Diphenyl-1,3-dioxolan-2-yl)phenoxy)(tert-butyl)dimethylsilane

    OSAJIMA Hiroyuki, OKANO Kentaro, TOKUYAMA Hidetoshi, FUKUYAMA Tohru

    2009, Org. Synth., 86, 130 - 140, English

    [Refereed]

    Scientific journal

  • Tetsuji Kubo, Chiharu Katoh, Ken Yamada, Kentaro Okano, Hidetoshi Tokuyama, Tohru Fukuyama

    A unique combination of CuI and CsOAc was found to catalyze aryl amination under mild conditions. The reaction takes place at room temperature or at 90 degrees C with broad functional group compatibility. The intramolecular reaction was able to form five-, six-, and seven-membered rings with various protecting groups on the nitrogen atom. The scope of the intermolecular amination, as well as its applications to unsymmetrical N,N'-dialkylated phenylenediamines, was investigated. (C) 2008 Elsevier Ltd. All rights reserved.

    PERGAMON-ELSEVIER SCIENCE LTD, Dec. 2008, TETRAHEDRON, 64 (49), 11230 - 11236, English

  • Kentaro Okano, Kei-ichiro Okuyama, Tohru Fukuyama, Hidetoshi Tokuyama

    Scope and limitations of the debenzylation conditions for aryl benzyl ether, which was developed during our synthetic studies on yatakemycin, were investigated. The chemoselective debenzylation proceeds at low temperature with a combination of BCl(3) and pentamethylbenzene as a cation scavenger in the presence of various functional groups.

    GEORG THIEME VERLAG KG, Aug. 2008, SYNLETT, (13), 1977 - 1980, English

    [Refereed]

    Scientific journal

  • Kentaro Okano, Kei-ichiro Okuyama, Tohru Fukuyama, Hidetoshi Tokuyama

    Scope and limitations of the debenzylation conditions for aryl benzyl ether, which was developed during our synthetic studies on yatakemycin, were investigated. The chemoselective debenzylation proceeds at low temperature with a combination of BCl(3) and pentamethylbenzene as a cation scavenger in the presence of various functional groups.

    GEORG THIEME VERLAG KG, Aug. 2008, SYNLETT, (13), 1977 - 1980, English

    Scientific journal

  • Kentaro Okano, Hidetoshi Tokuyama, Tohru Fukuyama

    A convergent total synthesis of (+)-yatakemycin was accomplished by a 20-step sequence in 13 % overall yield. The regioselective ring opening of (S)-epichlorohydrin with a 2,6-dibromophenyllithium derivative enabled us to introduce a chiral carbon center, which was required for the stereoselective construction of the cyclopropane ring. The five aryl-nitrogen bonds in (+)-yatakemycin were constructed by a mild copper-mediated aryl amination that utilized the combination of CuI with CsOAc. The efficient and chemoselective debenzylation of aryl benzyl ether with BCl3 in the presence of pentamethylbenzene was developed. With these new methodologies, the subgram-scale synthesis of (+)-yatakemycin was achieved.

    WILEY-V C H VERLAG GMBH, 2008, CHEMISTRY-AN ASIAN JOURNAL, 3 (2), 296 - 309, English

    [Refereed]

    Scientific journal

  • Kentaro Okano, Hidetoshi Tokuyama, Tohru Fukuyama

    AMER CHEMICAL SOC, Jun. 2006, JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 128 (22), 7136 - 7137, English

    [Refereed]

    Scientific journal

  • Y Kawashima, K Okano, K Nozaki, T Hiyama

    Hydroesterification of vinylarenes using a mixture of PdCl2 and monodentate phosphorus ligands as a catalyst was studied. As ligands, menthyldiphenylphosphine (MDPP). neomenthyldiphenylphosphine (NMDPP), and dicyclohexyl(phenyl)phosphine (Cy2PPh) were effective to obtain branched esters with high regioselectivity under the moderate reaction conditions Without additives such as acids. Not only electronic effects but also steric effects of the cycloalkyl groups were revealed to be significant in order to achieve high catalytic activity. When (S)-2-dicyclopentylphosphino-2'-methoxy-1,1'-binaphthyl was used for the asymmetric hydroesterification of 2-methoxy-6-vinylnaphthalene, (S)-naproxen methyl ester was obtained with 53% ee.

    CHEMICAL SOC JAPAN, Feb. 2004, BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 77 (2), 347 - 355, English

    [Refereed]

    Scientific journal

  • K Okano, H Tokuyama, T Fukuyama

    [GRAPHICS] A mild intermolecular copper-mediated amination of aryl iodides has been developed. The reaction takes place at room temperature or heating at 90 degreesC and tolerates halogens attached to the aromatic ring. Its synthetic applications include a synthetic protocol for unsymmetrical N,N'-dialkylated phenylenediamines and both a stepwise and a general synthetic method for N-aryl secondary amines via Ns-anilides (readily obtained by reaction of the Ns-amide).

    AMER CHEMICAL SOC, Dec. 2003, ORGANIC LETTERS, 5 (26), 4987 - 4990, English

    [Refereed]

    Scientific journal

  • Atsunori Mori, Keisuke Fujita, Chihiro Kubota, Toyoko Suzuki, Kentaro Okano, Takuya Matsumoto, Takashi Nishino, Masaki Horie

    Differently substituted thiophene−thiophene alternating copolymer was formally synthesized employing a halobithiophene as a monomer. Nickel-catalyzed polymerization of bithiophene, which substituent at the 3-position involves alkyl, fluoroalkyl, or oligosiloxane containing alkyl group, afforded the corresponding copolymer in good to excellent yield. The solubility test to organic solvents was performed to reveal several copolymers show a superior solubility. X-ray diffraction analysis of the thin film of the alternating copolymer composed of methyl and branched oligosiloxane substituents was also performed and found that the film suggested formation of dual-layered structure.

    Beilstein Institut, 30 Dec. 2019

  • Kentaro Okano, Yoshiki Yamane, Aiichiro Nagaki, Atsunori Mori

    AbstractSelective trapping of (4,5-dibromo-2-thienyl)lithium, known to undergo halogen dance, was achieved in a flow microreactor. This transient thienyllithium, generated by mixing 2,3-dibromothiophene and lithium diisopropylamide at –78 °C for 1.6 seconds, reacted with benzaldehyde. The reaction system is also applicable to other carbonyl compounds to afford the corresponding adducts in good yields. Moreover, the established conditions permit the conversion of 2,5-dibromothiophene into a mixture of the two constitutional isomers. The contrasting results are discussed on the basis of the reaction pathway.

    Georg Thieme Verlag KG, Dec. 2020, Synlett, 31 (19), 1913 - 1918

    Scientific journal

MISC

  • ラジカル転位環化反応を用いた(-)‐Histrionicotoxinの全合成

    佐藤学, 我妻弘基, 大学明広, 高須清誠, 岡野健太郎, 徳山英利

    02 Nov. 2015, 複素環化学討論会講演要旨集, 45th, 311 - 312, Japanese

  • Total Synthesis of (-)-Haouamine B Pentaacetate and Structural Revision of Haouamine B

    Hidetoshi Tokuyama, Kentaro Okano, Kenji Sugimoto, Yuichi Momoi, Keiichiro Okuyama, Hiroki Toya

    GEORG THIEME VERLAG KG, Mar. 2015, SYNTHESIS-STUTTGART, 47 (5), A42 - A45, English

    Others

  • (-)‐Penitrem Eの合成研究

    OTSU TAKANORI, YOSHII YU, HOSOKAWA NORIHIKO, TAKASU KIYOSEI, OKANO KENTARO, TOKUYAMA HIDETOSHI

    27 Oct. 2014, 有機合成シンポジウム講演要旨集, 106th, 52 - 53, Japanese

  • ラジカル転位環化反応を用いるアザスピロ環の不斉構築を基盤としたHistrionicotoxinの合成研究

    OKANO KENTARO, WAGATSUMA HIROKI, SATO MANABU, DAIGAKU AKIHIRO, TAKASU KIYOSEI, TOKUYAMA HIDETOSHI

    22 Oct. 2014, 反応と合成の進歩シンポジウム講演要旨集, 40th, 100, Japanese

  • ラジカル転位環化反応を用いたHistrionicotoxin類の合成研究

    AZUMA HIROKI, SATO MANABU, DAIGAKU AKIHIRO, TAKASU KIYOSEI, OKANO KENTARO, TOKUYAMA HIDETOSHI

    06 Jun. 2014, シンポジウム「モレキュラー・キラリティー」講演要旨集, 2014, (JA)103,(EN)102, Japanese

  • 不安定な七員環をいかにつくるか?アセチルアラノチンの全合成

    TOKUYAMA Hidetoshi, OKANO Kentaro

    2014, 化学, 69 (2), 68 - 69, Japanese

    [Refereed][Invited]

    Introduction commerce magazine

  • Kentaro Okano, Hidetoshi Tokuyama, Tohru Fukuyama

    ROYAL SOC CHEMISTRY, 2014, CHEMICAL COMMUNICATIONS, 50 (89), 13650 - 13663, English

    [Refereed][Invited]

    Introduction scientific journal

  • Kentaro Okano

    Total syntheses of yatakemycin, PDE-II, dictyodendrins, and heptaphylline are described. This article focuses on the formation of aryl carbon-nitrogen bonds by two methods: first by an aromatic amination reaction using a combination of CuI and CsOAc, and then by a benzyne-mediated one-pot cyclization-functionalization sequence. The aryl amination reaction shows a high functional group compatibility and applicability for highly hindered substrates. The utility of this reaction has been fully demonstrated through a total synthesis of yatakemycin, which features the regioselective ring opening of (S)-epichlorohydrin with 2,6-dibromophenyllithium species and the efficient deprotection of benzyl groups of aryl benzyl ether with BCl3 in the presence of pentamethylbenzene. The copper-mediated aryl amination reaction was applied to a one-pot double aryl amination for facile access to the highly substituted pyrroloindole skeleton, which led to a concise total synthesis of PDE-II. A highly efficient total synthesis of dictyodendrins A-E was accomplished by the development of a novel benzyne-mediated one-pot indoline formation/cross-coupling sequence for the construction of a highly substituted key indoline intermediate. Peripheral substituents were introduced onto this intermediate in a modular fashion to complete the total synthesis of dictyodendrins A-E. The utility of the one-pot benzyne-mediated cyclization-functionalization reaction was demonstrated by the total synthesis of carbazole alkaloid, heptaphylline.

    PHARMACEUTICAL SOC JAPAN, Oct. 2013, YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN, 133 (10), 1065 - 1078, Japanese

    [Refereed][Invited]

    Book review

  • Yusuke Iwama, Kentaro Okano, Hidetoshi Tokuyama

    This review focuses on synthetic studies on mersicarpine that has a characteristic skeleton including seven-membered cyclic imine fused with indoline and delta-lactam. After a brief discussion of structural features and proposed biogenesis of this compound, several synthetic efforts toward construction of mersicarpine core are described. Total syntheses of mersicarpine are described including Kerr's racemic synthesis utilizing a formation of seven-membered cyclic imine from alpha-hydroxyketone prepared by oxidation of indole, racemic syntheses of the Kerr's synthetic intermediate by Zard and Han, the first enantiocontrolled total synthesis by Fukuyama based on the construction of seven-membered alpha-hydroxyimine by autoxidation of azepinoindole, and the second enantiocontrolled synthesis by Tokuyama employing a DIBALH-mediated ring-expansion reaction of cyclic ketoxime fused with indole.

    SOC SYNTHETIC ORGANIC CHEM JPN, Sep. 2013, JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 71 (9), 926 - 934, Japanese

    [Refereed][Invited]

    Introduction scientific journal

  • 不斉転写型ラジカル転位環化反応を利用した(-)‐HTXの合成研究

    AZUMA HIROKI, DAIGAKU AKIHIRO, TAKASU KIYOSEI, OKANO KENTARO, TOKUYAMA HIDETOSHI

    02 Jun. 2012, 万有生命科学振興国際交流財団仙台シンポジウム, 23rd, 62, Japanese

  • 不斉転写型ラジカル転位環化反応を利用した(-)‐Histrionicotoxinの合成研究

    AZUMA HIROMOTO, DAIGAKU AKIHIRO, TAKASU KIYOSEI, OKANO KENTARO, TOKUYAMA HIDETOSHI

    30 May 2012, 有機合成シンポジウム講演要旨集, 101st, 113 - 116, Japanese

  • ラジカル転位環化反応を利用した(-)‐Histrionicotoxinの合成研究

    AZUMA HIROKI, DAIGAKU AKIHIRO, OKANO KENTARO, TAKASU KIYOSEI, TOKUYAMA HIDETOSHI

    05 Mar. 2012, 日本薬学会年会要旨集, 132nd (2), 111, Japanese

  • Penitrem Eの合成研究

    YOSHII YU, OTSU TAKANORI, OKANO KENTARO, HOSOKAWA NORIHIKO, TAKASU KIYOSEI, TOKUYAMA HIDETOSHI

    05 Mar. 2012, 日本薬学会年会要旨集, 132nd (2), 140, Japanese

  • Petrosinの不斉全合成および抗HIV活性に関する構造活性相関研究

    SATO TAKAHITO, TOTANI HIROKI, OKANO KENTARO, TAKASU KIYOMASA, IHARA MASATAKA, TAKAHASHI JUN, TANAKA HARUO, TOKUYAMA HIDETOSHI

    05 Mar. 2012, 日本薬学会年会要旨集, 132nd (2), 219, Japanese

  • 23 Total Synthesis of (-)-Perhydrohistrionicotoxin using Radical Translocation-Cyclization Reaction(Oral Presentation)

    Azuma Hiroki, Daigaku Akihiro, Fujitani Manabu, Okano Kentaro, Takasu Kiyosei, Tokuyama Hidetoshi

    Histrionicotoxin (1) and perhydrohistrionicotoxin (2), are non-competitive blockers of nicotinic acetylcholine-acceptors. The important bioactivity and the characteristic azaspirocyclic skeleton have attracted considerable interests from the synthetic community. However, there are few effective methods for enantiocontrolled construction of the azaspirocyclic ring. Herein, we report a diastereoselective construction of the core six-membered spirolactam utilizing a radical translocation-cyclization strategy and application to a total synthesis of (-)-2. In our preliminary experiments, the radical reaction using enantiomerically pure lactam 6 resulted in significant decrease of the enantiomeric purity, which indicated inversion of the sp^3 radical center generated via 1,5-hydrogen radical shift was much faster than cyclization. Based on these results, we considered a stereoselective radical reaction with chiral-transfer from other stereocenter introduced on the side chain. With this idea in mind, we examined radical reaction with diastereomeric 16 or 19 having the same chiral side chain. As we expected, the reactions of both compounds gave the same 18 albeit in low yield probably due to the undesired radical translocation to the a-position of the silyloxy group. The low yielding problem was circumvented by conducting the reaction with ketal 22 with no hydrogen. Encouraged by this successful result, we then investigated the diastereoselective radical reaction of a substrate with a chiral ketal moiety derived from a C_2-symmetrical diol. Among a variety of diols tested, we found that 2,4-pentanediol was effective for achieving high enantiomeric excess. Based on the formation of the azaspirocyclic compound 31, we accomplished a total synthesis of (-)-perhydrohistrionicotoxin (2).

    Symposium on the Chemistry of Natural Products Steering Committee, 2012, Symposium on the Chemistry of Natural Products, symposium papers, 54 (0), 133 - 138, Japanese

  • Petrosinの不斉全合成および抗HIV活性に関する構造活性相関研究

    SATO TAKAHITO, TOTANI HIROKI, OKANO KENTARO, TAKASU KIYOSEI, IHARA MASATAKA, TAKAHASHI JUN, TANAKA HARUO, TOKUYAMA HIDETOSHI

    2012, 日本薬学会東北支部大会講演要旨集, 51st, 32, Japanese

  • (-)‐および(+)‐petrosinの全合成

    TOTANI HIROKI, OKANO KENTARO, TAKASU KIYOSEI, IHARA MASATAKA, TAKAHASHI JUN, TANAKA HARUO, TOKUYAMA HIDETOSHI

    05 Mar. 2011, 日本薬学会年会要旨集, 131st (2), 143, Japanese

  • Kentaro Okano, Tohru Fukuyama, Hidetoshi Tokuyama

    This article focuses on the development of an aromatic amination reaction using CuI and CsOAc and its application to total syntheses of nitrogen-containing cyclic natural products. The reaction conditions present several unprecedented features that have not been observed in conventional palladium-catalyzed systems, including high functional group compatibility (e.g., N-alloc-and sp2-Br are retained) and applicability for highly hindered substrates. The utility of this reaction has been fully demonstrated through total syntheses of duocarmycins, yatakemycin, and PDE-II.

    Oct. 2010, Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 68 (10), 1036 - 1046, Japanese

  • Kentaro Okano, Tohru Fukuyama, Hidetoshi Tokuyama

    This article focuses on the development of an aromatic amination reaction using CuI and CsOAc and its application to total syntheses of nitrogen-containing cyclic natural products. The reaction conditions present several unprecedented features that have not been observed in conventional palladium-catalyzed systems, including high functional group compatibility (e.g., N-alloc-and sp(2)-Br are retained) and applicability for highly hindered substrates. The utility of this reaction has been fully demonstrated through total syntheses of duocarmycins, yatakemycin, and PDE-II.

    SOC SYNTHETIC ORGANIC CHEM JPN, Oct. 2010, JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 68 (10), 1036 - 1046, Japanese

    [Refereed]

    Introduction scientific journal

  • (-)および(+)‐Petrosinの全合成

    TOYA HIROKI, OKANO KENTARO, TAKAHASHI ATSUSHI, TANAKA HARUO, TAKASU KIYOSEI, IHARA MASATAKA, TOKUYAMA HIDETOSHI

    14 Sep. 2010, 複素環化学討論会講演要旨集, 40th, 73 - 74, Japanese

  • (-)および(+)‐Petrosinの全合成

    OKANO KENTARO, TOYA HIROKI, TAKAHASHI ATSUSHI, TANAKA HARUO, TAKASU KIYOSEI, IHARA MASATAKA, TOKUYAMA HIDETOSHI

    02 Sep. 2010, 有機合成化学セミナー講演予稿集, 27th, 112, Japanese

  • (-)および(+)‐Petrosinの全合成

    TOYA HIROKI, OKANO KENTARO, TAKAHASHI ATSUSHI, TANAKA HARUO, TAKASU KIYOSEI, IHARA MASATAKA, TOKUYAMA HIDETOSHI

    01 Sep. 2010, 天然有機化合物討論会講演要旨集, 52nd, 229 - 234, Japanese

  • (±)‐Lepadiformine Aの全合成

    FUJITANI MANABU, TSUCHIYA MASAMI, OKANO KENTARO, TAKASU KIYOSEI, IHARA MASATAKA, TOKUYAMA HIDETOSHI

    05 Mar. 2010, 日本薬学会年会要旨集, 130th (2), 141, Japanese

  • アリル位C-H酸化が切り開くマクロリド合成の新展開

    岡野 健太郎

    2010, ファルマシア, 46 (6), 548 - 549, Japanese

    [Refereed]

    Introduction scientific journal

  • 抗HIV活性を示す(-)‐Petrosinの不斉全合成

    OKANO KENTARO, TOYA HIROKI, TAKAHASHI ATSUSHI, TANAKA HARUO, TAKASU KIYOSEI, IHARA MASATAKA, TOKUYAMA HIDETOSHI

    10 Nov. 2009, メディシナルケミストリーシンポジウム講演要旨集, 28th, 170 - 171, Japanese

  • Synthetic Studies on(-)-Histrionicotoxin by Radical Translocation-Cyclization

    DAIGAKU AKIHIRO, OKANO KENTARO, TAKASU KIYOSEI, TOKUYAMA HIDETOSHI

    25 Sep. 2009, 複素環化学討論会講演要旨集, 39th, 37 - 38, Japanese

  • Lepadiformine類の合成研究

    FUJITANI MANABU, TSUCHIYA MASAMI, OKANO KENTARO, TAKASU KIYOSEI, IHARA MASATAKA, TOKUYAMA HIDETOSHI

    19 Sep. 2009, 化学系学協会東北大会プログラムおよび講演予稿集, 2009, 73, Japanese

  • 9環性インドールアルカロイドPenitrem Eの合成研究

    OTSU TAKANORI, HOSOKAWA NORIHIKO, TAKASU KIYOSEI, OKANO KENTARO, TOKUYAMA HIDETOSHI

    11 Sep. 2009, 有機合成化学セミナー講演予稿集, 26th, 89, Japanese

  • 9環性インドールアルカロイドPenitrem Eの合成研究

    OTSU TAKANORI, HOSOKAWA NORIHIKO, OKANO KENTARO, TAKASU KIYOSEI, TOKUYAMA HIDETOSHI

    05 Mar. 2009, 日本薬学会年会要旨集, 129th (2), 110, Japanese

  • Petrosinの全合成

    TOTANI HIROKI, OKANO KENTARO, TAKASU KIYOSEI, IHARA MASATAKA, TOKUYAMA HIDETOSHI

    2009, 有機合成シンポジウム講演要旨集, 95th, 145 - 148, Japanese

  • Kentaro Okano

    Recent development of synthetic studies on novel marine alkaloids, haouamine A and B, is described. Haouamines have attracted considerable attention of synthetic chemists because of their unique structure and selective activity against human colon carcinoma cell line HT-29, however, only two groups have so far reported successful formation of their highly strained 3-aza-[7]-paracyclophane core. This review focuses on synthetic efforts to construct the core skeleton of haouamines reported by Baran and Wipf.

    SOC SYNTHETIC ORGANIC CHEM JPN, Apr. 2008, JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 66 (4), 387 - 388, Japanese

    [Refereed]

    Book review

  • 抗HIV作用を持つPetrosinの合成研究

    TOYA HIROKI, OKANO KENTARO, TAKASU KIYOMASA, IHARA MASATAKA, TOKUYAMA HIDETOSHI

    05 Mar. 2008, 日本薬学会年会要旨集, 128th (2), 15, Japanese

  • (-)‐ヒストリオニコトキシンの合成研究

    DAIGAKU AKIHIRO, OKANO KENTARO, TAKASU KIYOMASA, TOKUYAMA HIDETOSHI

    05 Mar. 2008, 日本薬学会年会要旨集, 128th (2), 137, Japanese

  • Lepadiformine類の合成研究

    FUJITANI MANABU, TSUCHIYA MASAMI, OKANO KENTARO, TAKASU KIYOSEI, IHARA MASATAKA, TOKUYAMA HIDETOSHI

    2008, 日本薬学会東北支部大会講演要旨集, 47th, 20, Japanese

  • (-)‐Histrionicotoxinの合成研究

    DAIGAKU AKIHIRO, OKANO KENTARO, TAKASU KIYOSEI, TOKUYAMA HIDETOSHI

    2008, 日本薬学会東北支部大会講演要旨集, 47th, 20, Japanese

  • 抗HIV作用を持つPetrosinの合成研究

    TOTANI HIROKI, OKANO KENTARO, TAKASU KIYOSEI, IHARA MASATAKA, TOKUYAMA HIDETOSHI

    2007, 日本薬学会東北支部大会講演要旨集, 46th, 19, Japanese

Books etc

  • 天然物合成で活躍した反応 実験のコツとポイント

    OKANO KENTARO

    Joint work, 化学同人, 2011, Japanese

    Scholarly book

  • 天然物の全合成 2000〜2008(日本)

    OKANO KENTARO

    Joint work, 化学同人, 2009, Japanese

    Scholarly book

  • 演習で学ぶ有機反応機構

    OKANO KENTARO

    Joint work, 化学同人, 2005, Japanese

    Scholarly book

Presentations

  • 不安定カルボアニオンの制御を基盤とするヘテロ芳香族化合物の官能基化(招待講演)

    OKANO Kentaro

    日本薬学会北陸支部 特別講演会, 14 Dec. 2018, Japanese, Domestic conference

    [Invited]

    Invited oral presentation

  • ハロゲンダンスの制御を基盤とするヘテロ芳香族化合物の官能基化

    OKANO Kentaro

    第4回近畿薬学シンポジウム:化学系の若い力, 29 Sep. 2018, Japanese, Domestic conference

    [Invited]

    Invited oral presentation

  • 機能性チオフェンの構造設計と精密重合

    MORI ATSUNORI, FUJITA KEISUKE, OGURA TADAYUKI, KUBOTA CHIHIRO, OKANO KENTARO, FUNAHASHI MASAHIRO

    第67回高分子討論会, Sep. 2018, Japanese, 高分子学会, 北海道大学, Domestic conference

    [Invited]

    Invited oral presentation

  • Synthesis of water-soluble regioregular polythiophenes

    MORI ATSUNORI, FUJITA KEISUKE, OGURA TADAYUKI, KUBOTA CHIHIRO, OKANO KENTARO, FUNAHASHI MASAHIRO

    The 22th International Symposium on Advanced Display Materials and Devices (ADMD 2018), Jul. 2018, English, Ulsan National Institute of Science and Gechnology (UNIST), Jeju, Korea, International conference

    [Invited]

    Invited oral presentation

  • ブロモチオフェンの金ナノ粒子上におけるハロゲンダンス

    AOKI Masato, MIYAGAQA Naoki, OKANO KENTARO, MORI Astunori

    日本化学会第98春季年会, Mar. 2018, Japanese, 日本化学会, 日本大学船橋キャンパス, Domestic conference

    Oral presentation

  • Recent Development of Halogen Dance

    OKANO KENTARO

    International Congress on Pure & Applied Chemistry (ICPAC) 2018, Mar. 2018, English, Siem Reap, Cambodia, International conference

    [Invited]

    Invited oral presentation

  • ハロゲンダンスを基盤としたヘテロ芳香族化合物の集積型官能基化

    OKANO KENTARO

    新学術領域研究「反応集積化が導く中分子戦略:高次生物機能分子の創製平成29年度第5回成果報告会, Jan. 2018, Japanese, 大阪大学豊中キャンパス, Domestic conference

    Oral presentation

  • Deprotonation of Dibromothiophenes Controlled by Flash Chemistry

    OKANO KENTARO, RIKAKO TADA, YOSHIKI YAMANE, AIICHIRO NAGAKI, JUNICHI YOSHIDA, MORI ATSUNORI

    The First International Conference on Automated Flow and Microreactor Synthesis(ICAMS-1), Jan. 2018, English, 大阪, International conference

    Poster presentation

  • Synthesis of Thienoindoles by Halogen Dance and Ligand-Controlled One-Pot Sequential Coupling Reactions

    YUKI HAYASHI, OKANO KENTARO, MORI ATSUNORI

    The 11th International Symposium on Integrated Synthesis, Nov. 2017, English, 淡路島, International conference

    Poster presentation

  • Synthesis of Furan-Dimer Based Biopolyester

    NAOKI MIYAGAWA, TADAYUKI OGURA, OKANO KENTARO, TAKUYA MATSUMOTO, TAKASHI NISHINO, MORI ATSUNORI

    The 11th International Symposium on Integrated Synthesis, Nov. 2017, English, 淡路島, International conference

    Poster presentation

  • Regiocontrolled Halogen Dance of α-Bromothiophenes and α-Bromofurans

    DAICHI MARI, NAOKI MIYAGAWA, OKANO KENTARO, MORI ATSUNORI

    The 11th International Symposium on Integrated Synthesis, Nov. 2017, English, 淡路島, International conference

    Poster presentation

  • Deprotonation of Dibromothiophenes Controlled by Flash Chemistry

    RIKAKO TADA, YOSHIKI YAMANE, AIICHIRO NAGAKI, JUNICHI YOSHIDA, OKANO KENTARO, MORI ATSUNORI

    The 11th International Symposium on Integrated Synthesis, Nov. 2017, English, 淡路島, International conference

    Poster presentation

  • ハロゲンダンスを用いる多置換ヘテロ芳香族化合物の合成

    OKANO KENTARO, MORI ATSUNORI

    第35回メディシナルケミストリーシンポジウム, Oct. 2017, Japanese, 名古屋大学, Domestic conference

    Poster presentation

  • 新規合成方法論の開発を基盤とする含窒素高次縮環天然物の全合成(奨励賞受賞講演)

    OKANO KENTARO

    第34回有機合成化学セミナー, Sep. 2017, Japanese, 金沢市文化ホール, Domestic conference

    [Invited]

    Invited oral presentation

  • 高歪み中間体の効率的発生方法の開発

    HIOKI YUTO, OKANO KENTARO, MORI ATSUNORI

    GSCシンポジウム, Jul. 2017, Japanese, 東京国際フォーラム・ホール, Domestic conference

    Poster presentation

  • ハロゲンダンスを基盤としたヘテロ芳香族化合物の集積型官能基化

    OKANO KENTARO

    新学術領域研究「反応集積化が導く中分子戦略:高次生物機能分子の創製平成29年度第4回成果報告会, Jul. 2017, Japanese, 京都大学桂キャンパス船井講堂, Domestic conference

    Poster presentation

  • マグネシウムビスアミドを用いるシクロアルキンの脱プロトン的発生法の開発

    HIOKI YUTO, OKANO KENTARO, MORI ATSUNORI

    第111回有機合成シンポジウム, Jun. 2017, Japanese, 有機合成化学協会, 岡山大学津島キャンパス, Domestic conference

    Oral presentation

  • Control of transient anion species for synthesis of multiply substituted heteroaromatic compounds

    OKANO Kentaro

    MPI-KobeU-RIKEN Joint Symposium, 21 Feb. 2017, English, International conference

    [Invited]

    Invited oral presentation

  • フルフラールを原料とする共役系ポリマーの合成

    MURASE YUKI, ASHIDA KANA, MIYAGAWA NAOKI, OKANO KENTARO, MORI ATSUNORI

    高分子研究会(神戸), Jul. 2016, Japanese, 高分子学会関西支部, 神戸県民会館, Domestic conference

    Poster presentation

  • Kinetic Resolution of Heterobiaryl Derivatives with Winding-vine-shaped Molecular Asymmetry

    MARUHASHI KAZUKI, YOICHI OKAYAMA, TOYOMORI YUKA, OKANO KENTARO, MORI ATSUNORI

    Molecular Chirality Asia 2016 – Chiral Science and Technology: From Asia to the World –, Apr. 2016, English, Knowledge Capital Congress Convention Center, International conference

    Poster presentation

  • 炭素-塩素結合をもつチオフェン誘導体のC-H結合におけるカップリング反応によるチオフェン-チオフェン結合の生成

    FUJITA KEISUKE, NAKAGAWA NAOKI, SUNAHARA KAZUHIRO, YAMANE YOSHIKI, OKANO KENTARO, MORI ATSUNORI

    日本化学会第96春季年会, Mar. 2016, Japanese, 日本化学会, 同志社大学, Domestic conference

    Oral presentation

  • マグネシウムビスアミドを用いるブロモチオフェン類のハロゲンダンス

    YAMANE YOSHIKI, SUNAHARA KAZUHIRO, OKANO KENTARO, MORI ATSUNORI

    日本化学会第96春季年会, Mar. 2016, Japanese, 日本化学会, 同志社大学, Domestic conference

    Oral presentation

  • マグネシウムビスアミドを用いるエノールトリフラートの脱プロトン的シクロアルキン発生法の開発

    HIOKI YUTO, OKANO KENTARO, MORI ATSUNORI

    日本化学会第96春季年会, Mar. 2016, Japanese, 日本化学会, 同志社大学, Domestic conference

    Oral presentation

  • ハロゲンダンスを利用したポリアリールチオフェン類の効率的合成法の開発

    SUNAHARA KAZUHIRO, YAMANE YOSHIKI, OKANO KENTARO, MORI ATSUNORI

    日本化学会第96春季年会, Mar. 2016, Japanese, 日本化学会, 同志社大学, Domestic conference

    Oral presentation

  • つるまき状分子不斉を有するビチオフェン誘導体の速度論的光学分割

    ASHIDA SHIOMI, OKAYAMA YOICHI, TOYOMORI YUKA, OKANO KENTARO, MORI ATSUNORI

    日本化学会第96春季年会, Mar. 2016, Japanese, 日本化学会, 同志社大学, Domestic conference

    Oral presentation

  • つるまき状分子不斉を有するビスイミダゾール誘導体の速度論的光学分割

    MARUHASHI KAZUKI, INOUE RYO, JIN GUANHONG, OKANO KENTARO, MORI ATSUNORI

    日本化学会第96春季年会, Mar. 2016, Japanese, 日本化学会, 同志社大学, Domestic conference

    Oral presentation

  • チオフェン誘導体のC-Hカップリング重合における配位子効果の検討

    OGURA TADAYUKI, NAKAGAWA NAOKI, FUJIO MAKOTO, HASHIMOTO TAKAYOSHI, OKANO KENTARO, MORI ATSUNORI

    日本化学会第96春季年会, Mar. 2016, Japanese, 日本化学会, 同志社大学, Domestic conference

    Oral presentation

  • チオフェン誘導体のC-Hカップリング重合におけるモノマー構造多様性の検討

    NAKAGAWA NAOKI, OGURA TADAYUKI, FUJITA KEISUKE, SUMINO YUGO, FUKUI YUTA, OKANO KENTARO, MORI ATSUNORI

    日本化学会第96春季年会, Mar. 2016, Japanese, 日本化学会, 同志社大学, Domestic conference

    Oral presentation

  • カルボアニオンの反応性制御を基盤とする多置換ヘテロ芳香族化合物の合成

    OKANO Kentaro

    ヘテロ原子部会平成27年度第3回懇話会, 10 Feb. 2016, Japanese, Domestic conference

    [Invited]

    Invited oral presentation

  • 特異な骨格を有するアルカロイド類の合成研究

    OKANO Kentaro

    分子イメージングセミナー RIKEN Molecular Imaging Seminar, 29 Sep. 2015, Japanese, Domestic conference

    [Invited]

    Invited oral presentation

  • 特異な骨格を有するアルカロイド類の合成研究

    OKANO Kentaro

    岡山大学異分野融合研究育成支援事業「有機合成を基盤とした生体機能制御分子の創製」第2回講演会, 31 Jul. 2015, Japanese, Domestic conference

    [Invited]

    Invited oral presentation

  • Total Synthesis of (+)-Yatakemycin

    ICOB-5&ISCNP-25 IUPAC, International Conference on Biodiversity and Natural Product, 2006

    Poster presentation

  • (+)-Yatakemycinの全合成

    第48回天然有機化合物討論会, 2006

  • Total Synthesis of (+)-Yatakemycin

    ICOB-5&ISCNP-25 IUPAC, International Conference on Biodiversity and Natural Product, 2006

    Poster presentation

  • (+)-Yatakemycinの全合成

    第48回天然有機化合物討論会, 2006

  • Synthetic Studies on (+)-Yatakemycin

    2005環太平洋国際化学会議, 2005

    Poster presentation

  • (+)-ヤタケマイシンの全合成研究

    第87回有機合成シンポジウム, 2005

  • (+)-ヤタケマイシンの全合成研究

    第87回有機合成シンポジウム, 2005

  • Synthetic Studies on (+)-Yatakemycin

    2005環太平洋国際化学会議, 2005

    Poster presentation

Association Memberships

  • 国際複素環化学会

  • The Society of Synthetic Organic Chemistry, Japan

  • The Chemical Society of Japan

  • The Pharmaceutical Society of Japan

  • 近畿化学協会

  • 日本薬学会

  • 日本化学会

  • 有機合成化学協会

Research Projects

  • 短寿命炭素アニオンの捕捉を基盤とするヘテロ芳香環の直接的官能基化法の開発

    岡野 健太郎

    科学研究費補助金/基盤研究(B), Apr. 2019 - Mar. 2023, Principal investigator

    Competitive research funding

  • 高ひずみ短寿命中間体の実用的発生法の開発

    岡野 健太郎

    公益財団法人 ハーモニック伊藤財団, 2019年度助成金, Apr. 2019 - Mar. 2021, Principal investigator

    Competitive research funding

  • 高ひずみ短寿命炭化水素の実用的発生法の開発と機能性高分子の合成

    岡野 健太郎

    公益財団法人 総合工学振興財団, 令和元年度研究奨励, Apr. 2019 - Mar. 2020, Principal investigator

    Competitive research funding

  • 精密in situトランスメタル化を鍵とするハロゲンダンスの制御

    岡野 健太郎

    公益財団法人 京都技術科学センター, 2019年度研究開発助成, Apr. 2019 - Mar. 2020, Principal investigator

    Competitive research funding

  • 高ひずみ炭化水素前駆体の実用的合成と機能性分子の創製

    岡野 健太郎

    公益財団法人 東燃ゼネラル石油研究奨励・奨学財団, 第38回(平成30年度)東燃ゼネラル石油研究奨励助成, Mar. 2019 - Mar. 2020, Principal investigator

    Competitive research funding

  • ハロゲンダンスの制御を基盤とするヘテロ芳香族化合物の集積型合成

    岡野 健太郎

    科学研究費補助金/新学術領域研究, Apr. 2018 - Mar. 2020, Principal investigator

    Competitive research funding

  • 岡野 健太郎

    学術研究助成基金助成金/基盤研究(C), Apr. 2016 - Mar. 2019, Principal investigator

    Competitive research funding

  • カルボアニオンの反応性制御を基盤としたワンポット連続反応の開発

    岡野 健太郎

    公益財団法人 川西記念新明和教育財団, 平成28年度 研究助成金, Apr. 2016 - Mar. 2018, Principal investigator

    Competitive research funding

  • 岡野 健太郎

    科学研究費補助金/新学術領域研究, Apr. 2016 - Mar. 2018, Principal investigator

    Competitive research funding

  • 岡野 健太郎

    学術研究助成基金助成金/基盤研究(C), Apr. 2013 - Mar. 2016, Principal investigator

    Competitive research funding

  • 植物由来アコニチンアルカロイド類の合成研究

    岡野 健太郎

    公益財団法人 松籟科学技術振興財団, 研究助成金, Apr. 2014 - Mar. 2015, Principal investigator

    Competitive research funding

  • C-H活性化を鍵とする直接的ヘテロ原子導入法の開発

    岡野 健太郎

    科学研究費補助金/新学術領域研究, Apr. 2013 - Mar. 2015, Principal investigator

    Competitive research funding

  • 有用な生物活性を有するジチオジケトピペラジン天然物の合成研究

    岡野 健太郎

    公益財団法人 薬学研究奨励財団, 研究助成金グループA, Apr. 2013 - Mar. 2014, Principal investigator

    Competitive research funding

  • 動的速度論的分割を鍵とするアザスピロ環の不斉構築

    岡野 健太郎

    公益財団法人 アステラス病態代謝研究会, 研究助成金, Apr. 2012 - Mar. 2013, Principal investigator

    Competitive research funding

  • 多様な誘導体合成を指向した新規ジチオジケトピペラジン天然物の網羅的全合成

    岡野 健太郎

    公益財団法人 東京生化学研究会, 研究奨励金(Ⅰ), Apr. 2012 - Mar. 2013, Principal investigator

    Competitive research funding

  • マグネシウムビスアミドを用いる新規ベンザイン発生法の開発と生理活性天然物の全合成

    岡野 健太郎

    科学研究費補助金/若手研究(B), Apr. 2011 - Mar. 2013, Principal investigator

    Competitive research funding

  • 不斉転写型ラジカル反応を鍵とするHTXの合成研究

    岡野 健太郎

    公益信託 三菱化学研究奨励基金, 平成22年度研究助成金, Apr. 2010 - Mar. 2011, Principal investigator

    Competitive research funding

  • ベンザインを経由するワンポット連続的環化ー官能基化に基づく多置換複素環骨格構築法の開発と生理活性天然物の革新的全合成

    岡野 健太郎

    公益財団法人 アステラス病態代謝研究会, 研究助成金, Apr. 2010 - Mar. 2011, Principal investigator

    Competitive research funding

  • ベンザインを基軸とする多置換複素環化合物の新規合成法の開発と天然物合成への展開

    岡野 健太郎

    科学研究費補助金/若手研究(B), Apr. 2009 - Mar. 2011, Principal investigator

    Competitive research funding

  • 第41回アメリカ有機化学シンポジウム

    岡野 健太郎

    財団法人 薬学研究奨励財団, 研究者の海外派遣に対する補助, Jun. 2009 - Jun. 2009, Principal investigator

    Competitive research funding

  • テロメラーゼ阻害活性を有するディクティオデンドリン類の合成研究

    岡野 健太郎

    科学研究費補助金/スタートアップ, May 2007 - Mar. 2009, Principal investigator

    Competitive research funding

  • ヤタケマイシンをはじめとする複雑な含窒素環状化合物の合成研究

    岡野 健太郎

    科学研究費補助金/特別研究員奨励費, Apr. 2006 - Apr. 2007, Principal investigator

    Competitive research funding