Takao, Ken-ichi

写真a

Affiliation

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

Position

Professor

E-mail Address

E-mail address

Related Websites

External Links
Scopus Paper Info  
Paper Count: 124 Citation Count: 3163 h-index: 30

Click to view the Scopus page. The data was downloaded from Scopus API in April 14, 2026, via http://api.elsevier.com and http://www.scopus.com .

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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 】

  • Synthesis of Tetrahydro-β-carbolines via Cascade Sigmatropic Rearrangements

    Oka D., Ohtsuka T., Takao K.i., Ogura A.

    Advanced Synthesis and Catalysis 367 ( 3 )  2025.02

    ISSN  16154150

    　View Summary

    We have developed a synthesis for tetrahydro-β-carbolines involving cascade sigmatropic rearrangements. The substrates were conveniently prepared from parent anilines via a [2,3]-sigmatropic rearrangement and cyanomethylation. Silver-mediated decyanation afforded the corresponding iminium cation, which underwent a cascade consisting of an aza-Cope rearrangement, an aza-oxa-Cope rearrangement, an aromatization, and a Pictet-Spengler reaction, and tetrahydro-β-carbolines were obtained as the single product. The reaction involved seven bond scissions and four bond formations and was triggered by a single reagent.

  • Synthetic Studies of Polycyclic Polyprenylated Acylphloroglucinols: Asymmetric Construction of a Cyclohexanone Moiety

    Nanataki S., Aoki D., Onozawa H., Akiya T., Okuyama G., Abo K., Yoshida K., Ogura A., Takao K.I.

    Synlett 36 ( 10 ) 1375 - 1378 2025

    ISSN  09365214

    　View Summary

    As a common intermediate for polycyclic polyprenylated acylphloroglucinols (PPAPs), we successfully synthesized a cyclohexanone moiety that contains two adjacent stereocenters, one of which is a quaternary carbon. Our synthetic strategy relied on an asymmetric Claisen rearrangement using Oppolzer's camphorsultam and a regioselective Dieckmann condensation.

  • Antiproliferative activities through accelerating autophagic flux by basidalin and its analogs in human cancer cells

    Matagawa T., Sasazawa Y., Agui K., Fujimaki M., Kawano S., Ogura A., Takao K.i., Igarashi M., Simizu S.

    Bioorganic and Medicinal Chemistry Letters (Bioorganic and Medicinal Chemistry Letters)  104 2024.05

    ISSN  0960894X

    　View Summary

    Basidalin, isolated from the basidiomycete Leucoagaricus naucina, has previously demonstrated antibacterial and antitumor properties against murine cancer cells in vivo, but its effects on human cancer cells remain unknown. In this study, we found that basidalin possesses antiproliferative activity against human cancer cell lines. To elucidate the antiproliferative mechanism of basidalin, we focused on autophagy. Treatment with basidalin led to an increase in LC3-II expression level, and accelerated autophagic flux through an mTOR-independent pathway. Moreover, according to the structure–activity relationship analysis—including newly synthesized basidalin analogs—the formyl group, not the amino group, contributes to the antiproliferative activities of basidalin against human cancer cells. Additionally, the antiproliferative activity of basidalin analogs was strongly correlated with autophagy-inducing activity, indicating that basidalin exhibits antiproliferative activity through autophagy induction. These data suggest that basidalin, characterized by its ability to upregulate autophagic flux, emerges as a novel anticancer drug.

  • Open system massive synthesis of narrow-band blue and green fluorescent graphene quantum dots and their application in water sensing

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

    Journal of Materials Chemistry C (Journal of Materials Chemistry C)  12 ( 18 ) 6548 - 6558 2024.04

    ISSN  20507526

    　View Summary

    Graphene quantum dots (GQDs) are environmentally friendly fluorescent carbon-based nanomaterials. However, there is no report on the massive synthesis of GQDs with narrow-band fluorescence and a high photoluminescence quantum yield (PLQY) using a simple liquid-phase method under atmospheric conditions. In this study, GQDs were successfully synthesized in ∼100% product yield by heating phloroglucinol (PG) with Na3PO4·12H2O in 1,2-pentanediol at 180 °C for 6 h in an open system with air flow, followed by dialysis purification. The high product yield was attributed to the addition of Na3PO4·12H2O as a base catalyst, which promoted the dehydration-condensation reaction between PG molecules. The dispersion of PG derived GQDs (PG-GQDs) in ethanol resulted in blue fluorescence with a full width at half maximum of 32 nm and a PLQY of 54%. Further purification of PG-GQDs by silica gel column chromatography improved the PLQY to 75%. Fourier-transform infrared spectroscopy, 1H nuclear magnetic resonance spectroscopy, and X-ray photoelectron spectroscopy confirmed that dehydration-condensation reactions occurred not only between PGs but also between GQDs and 1,2-pentanediol. The binding of 1,2-pentanediol to the edges of GQDs suppressed the stacking of GQDs and prevented concentration quenching, resulting in a high PLQY. PG-GQDs exhibited negative fluorescence solvatochromism, i.e., the fluorescence wavelength blue-shifted with increasing solvent polarity. Dispersion of PG-GQDs in N-methyl-2-pyrrolidone (MP) resulted in green fluorescence with a PLQY of 96%. Dispersion of PG-GQDs in water resulted in blue fluorescence and a low PLQY of 6% at pH 7, while the PLQY was more than 50% at pH ≥ 11. Using these properties, the sensing of water (pH 13) in MP was investigated. The results showed that as the water content was increased from 0% to 100%, the fluorescence color gradually changed from green to blue and the fluorescence wavelength continuously shifted from 514 nm to 466 nm, indicating their applicability in water sensing.

  • 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.

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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 】

  • カロフィコ酸Aの全合成研究

    谷口広太郎・小椋章弘・高尾賢一

    [Domestic presentation]  日本化学会第106春季年会 (船橋市) , 

    2026.03
    , 

    Oral presentation (general)

  • ハイフェンロンBの全合成研究

    原田現輝・大田将馬・小椋章弘・高尾賢一

    [Domestic presentation]  日本化学会第106春季年会 (船橋市) , 

    2026.03
    , 

    Oral presentation (general)

  • 赤色光で駆動する新規ラジカル開始剤の開発

    牛山千聖・谷川麟太郎・篠原　杏・竹橋侑矢・高尾賢一・小椋章弘

    [Domestic presentation]  第54回複素環化学討論会 (東京) , 

    2025.10
    , 

    Poster presentation

  • グッチフェロンAおよびハイペレラトンAの全合成研究

    龍岡資将・滝本実里・七瀧智俊・小椋章弘・高尾賢一

    [Domestic presentation]  第67回天然有機化合物討論会 (仙台市) , 

    2025.09
    , 

    Poster presentation

  • Synthesis of Indoles via Aza-oxa-Cope Rearrangement

    Ryosuke Saito, Tomomi Ohtsuka, Tomoki Uchida, Daiki Oka, Ken-ichi Takao, and Akihiro Ogura

    [International presentation]  The Second Asian Conference for “MONODUKURI” Strategy by Synthetic Organic Chemistry (Okinawa) , 

    2025.07
    -
    2025.08
    , 

    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 】

  • BASIC ORGANIC CHEMISTRY

    2026

  • GRADUATE RESEARCH ON CHEMISTRY, LIFE SCIENCE, AND INFORMATICS 2

    2026

  • BACHELOR'S THESIS

    2026

  • SEMINAR IN APPLIED CHEMISTRY

    2026

  • TOPICS IN MOLECULAR CHEMISTRY AND CHEMICAL BIOLOGY 1

    2026

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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 】

  • 2025.12
    -
    Present

    代議員, 有機合成化学協会

  • 2023.02
    -
    2024.02

    事業委員長, 有機合成化学協会

  • 2022.02
    -
    2024.02

    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

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