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 】

  • 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.

  • Asymmetric Diels–Alder reaction between furans and propiolates

    Ogura A., Ito T., Moriya K., Horigome H., Takao K.i.

    Tetrahedron Letters （Tetrahedron Letters)  72 2021.05

    ISSN  00404039

    　View Summary

    We report the first asymmetric Diels–Alder reaction between furan and propiolates. Propiolate, a dienophile, was equipped with an Evans’ auxiliary and a sulfonyl group to control and facilitate diastereoselective cycloaddition. Treatment with furan as a diene and aluminium Lewis acid afforded a 7-oxabicyclo[2.2.1]heptadiene skeleton diastereoselectively. The origin of diastereoselectivity can be explained by chelation of aluminium center to carbonyl groups and oxygen of furan. Friedel–Crafts-type products were obtained when pyrrole was used as diene.

  • Glycothermally Synthesized Carbon Dots with Narrow-Bandwidth and Color-Tunable Solvatochromic Fluorescence for Wide-Color-Gamut Displays

    Yoshinaga T., Shinoda M., Iso Y., Isobe T., Ogura A., Takao K.I.

    ACS Omega （ACS Omega)  6 （ 2 ） 1741 - 1750 2021.01

    ISSN  2470-1343

    　View Summary

    Fluorescent carbon dots (CDs) represent a promising eco-friendly next-generation phosphor. However, most CDs exhibit broad photoluminescence (PL) spectra [full width at half-maximum (fwhm) over 60 nm]; few works on CDs with sharp PL spectra (fwhm less than 40 nm) have been reported. In addition, their syntheses and color tuning require harsh conditions of high temperatures, long reaction times, and high pressures with catalysts. Here, we successfully prepared narrow-bandwidth emissive CDs (fwhm of 27-40 nm) from phloroglucinol in a glycol solvent of 1,2-pentanediol at temperatures as low as 180 °C for a reaction duration of as short as 6 h under ambient conditions without any catalysts via an open reaction system in which dehydration and condensation reactions among phloroglucinol molecules were enhanced. We shifted the emission peak from 463 to 511 nm by selecting seven kinds of solvents with different polarities, that is, emission colors could be tuned from blue to green by taking advantage of fluorescence solvatochromism. The CD-dispersed polymer films showed a similar solvatochromic behavior and sharp PL spectra, verifying the feasibility of applying the CDs to displays with a wide color gamut.

  • Diaryliodonium Salt-Based Synthesis of N-Alkoxyindolines and Further Insights into the Ishikawa Indole Synthesis

    Shibata K., Takao K.I., Ogura A.

    Journal of Organic Chemistry （Journal of Organic Chemistry)  86 （ 15 ） 10067 - 10087 2021

    ISSN  00223263

    　View Summary

    A diaryliodonium salt-based strategy enabled the first systematic synthesis of rarely accessible N-alkoxyindoles. Mechanistic analyses suggested that the reaction likely involves reductive elimination of iodobenzene from iodaoxazepine via a four-membered transition state, followed by Meisenheimer rearrangement. Substrates with N-carbamate protection afforded indole in a manner similar to that of the Ishikawa indole synthesis. Preinstallation of a stannyl group as an iodonium salt precursor greatly expanded the substrate scope, and further mechanistic insights are discussed.

  • The stereoselective construction of all-carbon quaternary stereocenters by allylations and its application to synthetic studies of natural products

    Sakama A., Ogura A., Yoshida K., Takao K.I.

    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry （Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry)  78 （ 11 ） 1039 - 1047 2020.11

    ISSN  00379980

    　View Summary

    © 2020 Society of Synthetic Organic Chemistry. All rights reserved. The synthesis of organic compounds containing all.. carbon quaternary stereocenters through the addition of allylmetals to aldehydes is still a challenge. In this account we describe two methods to achieve this transformation stereoselectively: One involves the zinc-mediated Barbier-type allylation and the other allylboration of a sugar.. derived aldehyde. These methods were applied to the total synthesis of (+)-vibsanin A, and the synthesis of the tricyclic core of (-)-callophycoic acid A.

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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 】

  • 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82回有機合成化学協会関東支部（横浜国大）シンポジウム (横浜市) , 

    2022.05
    , 

    Oral presentation (general)

  • 赤色光を用いたBarton脱炭酸的ヘテロ原子導入反応の開発

    篠原　杏・山本拓樹・高尾賢一・小椋章弘

    第82回有機合成化学協会関東支部（横浜国大）シンポジウム (横浜市) , 

    2022.05
    , 

    Oral presentation (general)

  • ゼイラニジンの全合成研究

    名川啓史・楠畑光太郎・小椋章弘・高尾賢一

    日本化学会第102春季年会 (オンライン) , 

    2022.03
    , 

    Oral presentation (general)

  • ハイフェンロンAの全合成研究

    小林武史・横矢悠介・小椋章弘・高尾賢一

    日本化学会第102春季年会 (オンライン) , 

    2022.03
    , 

    Oral presentation (general)

  • グッチフェロンAの全合成研究

    七瀧智俊・青木太祐・小椋章弘・高尾賢一

    第81回有機合成化学協会関東支部シンポジウム (オンライン) , 

    2021.11
    , 

    Oral presentation (general)

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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

    2022

  • SEMINAR IN APPLIED CHEMISTRY

    2022

  • OFF-CAMPUS WORK-STUDY PROGRAM

    2022

  • LABORATORIES IN APPLIED CHEMISTRY B

    2022

  • INDEPENDENT STUDY ON FUNDAMENTAL SCIENCE AND TECHNOLOGY

    2022

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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
    -
    Present

    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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