Takao, Kenichi

写真a

Affiliation

Faculty of Science and Technology, Department of Applied Chemistry （Yagami）

Position

Professor

Related Websites

External Links
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Career 【 Display / hide 】

  • 1995.04
    -
    1996.03

    Research Chemist in Sagami Chemical Research Center

  • 1996.04
    -
    1998.03

    Instructor in Faculty of Pharmaceutical Sciences, Science University of Tokyo

  • 1998.04
    -
    2001.03

    Instructor in Faculty of Science and Technology, Keio University

  • 2001.04
    -
    2008.03

    Assistant Professor in Faculty of Science and Technology, Keio University

  • 2005.08
    -
    2006.07

    Research Associate, Scripps Florida, USA

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Academic Background 【 Display / hide 】

  • 1990.03

    Keio University, Faculty of Science and Technology, 応用化学科

    University, Graduated

  • 1992.03

    Keio University, Graduate School, Division of Science and Technology, 応用化学専攻

    Graduate School, Completed, Master's course

  • 1995.03

    Keio University, Graduate School, Division of Science and Technology, 応用化学専攻

    Graduate School, Completed, Doctoral course

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Academic Degrees 【 Display / hide 】

  • Ph.D., Keio University, Coursework, 1995.03

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Research Areas 【 Display / hide 】

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry (Organic Chemistry)

  • Nanotechnology/Materials / Synthetic organic chemistry (Synthetic Chemistry)

  • Life Science / Bioorganic chemistry (Organic Chemistry)

  • Life Science / Pharmaceutical chemistry and drug development sciences (Chemical Pharmaceutics)

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Books 【 Display / hide 】

  • 有機合成実験法ハンドブック　第２版

    高尾 賢一, 丸善出版, 2015.11

    Scope: 15.2.1　ヒドロキシ基の保護と脱保護

  • Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.

    Ken-ichi Takao and Kin-ichi Tadano, Elsevier: Amsterdam, 2013.04

    Scope: 161-187

  • ベーシックマスター有機化学

    高尾 賢一, オーム社, 2011.11

    Scope: 第14章　有機合成化学

  • Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.

    Yoshikazu Suzuki, Ken-ichi Takao, and Kin-ichi Tadano, Elsevier: Amsterdam, 2003.12

    Scope: 127-167

  • Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.

    Ken-ichi Takao, Jun Ishihara, Kin-ichi Tadano, Elsevier: Amsterdam, 2000.12

    Scope: 3-51

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Papers 【 Display / hide 】

  • Red-light-mediated Barton decarboxylation reaction and one-pot wavelength-selective transformations

    Yamamoto H., Yamaoka K., Shinohara A., Shibata K., Takao K.I., Ogura A.

    Chemical Science （Chemical Science)  14 （ 40 ） 11243 - 11250 2023.09

    ISSN  20416520

    　View Summary

    In organic chemistry, selecting mild conditions for transformations and saving energy are increasingly important for achieving sustainable development goals. Herein, we describe a red-light-mediated Barton decarboxylation using readily available red-light-emitting diodes as the energy source and zinc tetraphenylporphyrin as the catalyst, avoiding explosive or hazardous reagents or external heating. Mechanistic studies suggest that the reaction probably proceeds via Dexter energy transfer between the activated catalyst and the Barton ester. Furthermore, a one-pot wavelength-selective reaction within the visible light range is developed in combination with a blue-light-mediated photoredox reaction, demonstrating the compatibility of two photochemical transformations based on mechanistic differences. This one-pot process expands the limits of the decarboxylative Giese reaction beyond polarity matching.

  • Open system synthesis of narrow-bandwidth red-fluorescent carbon quantum dots with a function of multi-metal ion sensing

    Katakami R., Sato K., Ogura A., Takao K.I., Iso Y., Isobe T.

    Journal of Materials Chemistry C （Journal of Materials Chemistry C)  11 （ 12 ） 4143 - 4152 2023.03

    　View Summary

    Carbon quantum dots (CQDs) are environmentally friendly phosphors. However, there have been few reports on red-emitting CQDs with narrow-bandwidths, all of which were synthesized via solvothermal methods using autoclaves. Here, red-emitting CQDs were synthesized from 4,6-diaminoresorcinol dihydrochloride (DAR), which is an aromatic compound with electron-donating hydroxy and amino groups. The synthesis involved heating at 180 °C for 6 h in a high-boiling-point 1,2-pentanediol solvent in an open system without using autoclaves and catalysts. The DAR-derived-CQDs in ethanol exhibited red photoluminescence with a 0.14 eV full width at half-maximum that was comparable to that of narrow-bandwidth blue-fluorescent phloroglucinol (PG)-derived-CQDs. The red emission was attributed to a weakened quantum-size effect and electron-donating NH2 groups. The hydroxy groups of PG-derived-CQDs interacted with Al3+ and Fe3+ ions, resulting in fluorescence quenching. DAR-derived-CQDs have hydroxy and amino groups, which facilitate the fluorescence quenching for Al3+, Fe3+, Cu2+, and Pb2+ ions.

  • Asymmetric Synthesis of Cyclopentene Compounds Containing All-Carbon Quaternary Stereocenters by (3 + 2) Cycloaddition and Its Application in the Formal Synthesis of (R)-(-)-Puraquinonic Acid

    Oga M., Takamatsu Y., Ogura A., Takao K.I.

    Journal of Organic Chemistry （Journal of Organic Chemistry)  87 （ 13 ） 8788 - 8795 2022.07

    ISSN  00223263

    　View Summary

    A highly stereoselective (3 + 2) cycloaddition for the asymmetric synthesis of versatile cyclopentene compounds containing all-carbon quaternary stereocenters was developed. The phosphine-catalyzed reactions of alkynoates with α-alkylated electron-deficient alkenes bearing Oppolzer's camphorsultam showed high to excellent diastereoselectivities and perfect regioselectivities. The usefulness of this reaction was demonstrated in the concise formal synthesis of (R)-(-)-puraquinonic acid.

  • Elucidation of structure-activity relationship of humulanolides and identification of humulanolide analog as a novel HSP90 inhibitor

    Saegusa J., Osada Y., Miura K., Sasazawa Y., Ogura A., Takao K.i., Simizu S.

    Bioorganic and Medicinal Chemistry Letters （Bioorganic and Medicinal Chemistry Letters)  60 2022.03

    ISSN  0960894X

    　View Summary

    Humulanolides are natural products isolated from Asteriscus, and the isolation and total synthesis of many types of humulanolides have been reported. In this study, we evaluated anti-proliferative activity of twelve humulanolides against various human cancer cell lines and found that humulanolide analog E, which was newly designed and synthesized, exhibited the highest anti-proliferative activity. Structure-activity relationship analysis revealed that α,β-unsaturated carbonyl moieties in humulanolides play an important role for anti-proliferative activity. To identify molecular targets of humulanolide analog E, we investigated various cell-based and in vitro assays. Treatment with humulanolide analog E against human fibrosarcoma HT1080 cells increased the expression level of HSP70 protein and decreased the levels of AKT and CDK4, which are HSP90 client proteins. Moreover, humulanolide analog E inhibited refolding of denatured luciferase protein via suppression of HSP90 activity in vitro. These results suggest that humulanolide analog E possesses the anti-proliferative activity against human cancer cells by inhibiting HSP90 functions.

  • Development of TfOH-Catalyzed Spirocyclization by Intramolecular Friedel-Crafts-type 1,4-Addition: Application to the Total Synthesis of the Unusual Proaporphine Alkaloid (±)-Misrametine

    Yoshida K., Hidaka A., Fukami Y., Fujino Y., Imaizumi Y., Takao K.i., Kitagaki S.

    Chemistry - A European Journal （Chemistry - A European Journal)  28 （ 60 ）  2022

    ISSN  09476539

    　View Summary

    An effective method was developed for TfOH-catalyzed construction of spiroindanes and spirotetralines containing an all-carbon quaternary stereocenter. Intramolecular Friedel-Crafts-type 1,4-addition of the substrates which were di- or trimethoxybenzene and 2-cyclohexenone linked by an alkyl chain proceeded smoothly in the presence of 30 mol % of TfOH. A variety of spiroindanes and spirotetralines were obtained with moderate to excellent yield by this method. The reaction was successfully applied in the first total synthesis of the unusual proaporphine alkaloid (±)-misrametine, which included the gram-scale spirocyclization and selective O-demethylation used KCN in DMSO condition as key steps.

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Papers, etc., Registered in KOARA 【 Display / hide 】

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Reviews, Commentaries, etc. 【 Display / hide 】

  • 分子内野崎-檜山-高井-岸反応を用いた天然物の全合成

    高尾賢一

    THE CHEMICAL TIMES  ( No.3 ) 12 - 16 2018.07

    Article, review, commentary, editorial, etc. (scientific journal), Single Work

  • 有機化学の反応のしくみ

    高尾賢一・只野金一

    化学と教育 Vol.65   620 - 623 2017.12

    Article, review, commentary, editorial, etc. (scientific journal), Joint Work

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Presentations 【 Display / hide 】

  • 分子内野崎-檜山-高井-岸反応を用いた天然物の全合成

    高尾賢一

    有機合成化学協会関東支部ミニシンポジウム多摩2023 (八王子市) , 

    2023.11
    , 

    Oral presentation (invited, special)

  • ビールショウスキーシンの全合成研究

    寺内　頌・笹田祥吾・小椋章弘・高尾賢一

    第123回有機合成シンポジウム (東京) , 

    2023.11
    , 

    Oral presentation (general)

  • 連続的[3,3]-シグマトロピー転位を鍵としたテトラヒドロ-β-カルボリン合成法の開発

    岡　大輝・大塚友美・高尾賢一・小椋章弘

    第52回複素環化学討論会 (仙台市) , 

    2023.10
    , 

    Oral presentation (general)

  • カロフィコ酸Aの全合成研究究

    相崎来安・遠藤誠也・中村龍伍・小椋章弘・高尾賢一

    第65回天然有機化合物討論会 (東京) , 

    2023.09
    , 

    Poster presentation

  • シグマトロピー転位を駆使した原子効率の高いインドール合成法の開発

    斉藤綾佑・内田知希・高尾賢一・小椋章弘

    第122回有機合成シンポジウム (東京) , 

    2023.07
    , 

    Poster presentation

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Research Projects of Competitive Funds, etc. 【 Display / hide 】

  • 立体選択的な第四級不斉炭素構築法の開発とそれに基づく生物活性物質の合成

    2021.04
    -
    2025.03

    MEXT,JSPS, Grant-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (B), Principal investigator

  • Development and Application of Methods for Constructing New Skeletons by Use of Ring-Rearrangement Metathesis and Biomimetic Reactions

    2015.04
    -
    2018.03

    MEXT,JSPS, Grant-in-Aid for Scientific Research, Grant-in-Aid for Scientific Research (C), Principal investigator

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Awards 【 Display / hide 】

  • Astellas Award in Synthetic Organic Chemistry, Japan

    Ken-ichi Takao, 2006.11, 社団法人 有機合成化学協会, Development of Methods for Asymmetric Synthesis of Cyclobutanes and Application to Total Synthesis of Natural Products

    Type of Award： Award from Japanese society, conference, symposium, etc.

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Courses Taught 【 Display / hide 】

  • TOPICS IN ORGANIC SYNTHETIC CHEMISTRY

    2023

  • SEMINAR IN APPLIED CHEMISTRY

    2023

  • LABORATORIES IN APPLIED CHEMISTRY B

    2023

  • INDEPENDENT STUDY ON FUNDAMENTAL SCIENCE AND TECHNOLOGY

    2023

  • GRADUATE RESEARCH ON FUNDAMENTAL SCIENCE AND TECHNOLOGY 2

    2023

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Memberships in Academic Societies 【 Display / hide 】

  • The Chemical Society of Japan, 

    1990.04
    -
    Present

  • The Society of Synthetic Organic Chemistry, Japan, 

    1990.04
    -
    Present

  • The Pharmaceutical Society of Japan, 

    1996.04
    -
    Present

  • American Chemical Society, 

    1999.01
    -
    Present

  • The Japanese Society for Process Chemistry, 

    2003.04
    -
    Present
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Committee Experiences 【 Display / hide 】

  • 2022.02
    -
    Present

    理事（事業担当）, 有機合成化学協会

  • 2021.02
    -
    2023.02

    関東支部常任幹事, 有機合成化学協会

  • 2019.02
    -
    2021.02

    関東支部幹事, 有機合成化学協会

  • 2016.12
    -
    2021.12

    幹事, 新規素材探索研究会

  • 2016.01
    -
    2017.12

    化学グランプリ小委員会委員, 日本化学会

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