OGURA Akihiro

写真a

Affiliation

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

Position

Associate Professor

Related Websites

External Links
Scopus Paper Info  
Paper Count: 42 Citation Count: 712 h-index: 14

Click to view the Scopus page. The data was downloaded from Scopus API in July 26, 2026, via http://api.elsevier.com and http://www.scopus.com .

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Profile 【 Display / hide 】

  • 2022~ Senior Assistant Professor, Keio Univ. 2021~ Assistant Professor, Keio Univ. 2016~ Research Associate, Keio Univ. (Prof. Ken-ichi Takao) 2013~ Postdoctoral Fellow, RIKEN (Dr. Katsunori Tanaka) 2013 Ph.D. (Prof. Tohru Fukuyama) 2010~ JSPS Research Fellow, Univ. of Tokyo (Prof. Tohru Fukuyama) 2008~ Graduate School of Pharmaceutical Sciences, Univ. of Tokyo (Prof. Tohru Fukuyama)

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Career 【 Display / hide 】

  • 2010.04
    -
    2013.03

    JSPS, Research Fellow (DC1)

  • 2013.04
    -
    2016.03

    RIKEN, 特別研究員

  • 2016.04
    -
    2021.03

    Keio University, Faculty of Science and Technology Department of Applied Chemistry, 助教

  • 2021.04
    -
    2026.03

    Keio University, Faculty of Science and Technology Department of Applied Chemistry, 専任講師

  • 2025.04
    -
    Present

    理化学研究所, 客員研究員

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Academic Background 【 Display / hide 】

  • 2004.04
    -
    2008.03

    The University of Tokyo, Faculty of Pharmaceutical Sciences, Department of Pharmacy

  • 2008.04
    -
    2013.03

    東京大学大学院, 薬学系研究科, 分子薬学専攻

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Academic Degrees 【 Display / hide 】

  • 博士（薬学）, The University of Tokyo, Coursework, 2013.03

    Anisatin及びYuzurimineの全合成研究

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Licenses and Qualifications 【 Display / hide 】

  • Drivers License, Non-Professional, 2004.09

  • STEP Eiken, Grade Pre-1, 2005.02

  • Hazardous Materials Engineer's License, Class A, 2005.12

  • The Official Business Skill Test in Book-keeping, 2nd Grade, 2006.06

  • Pharmacist License, 2008.08

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Research Areas 【 Display / hide 】

  • Nanotechnology/Materials / Structural organic chemistry and physical organic chemistry

  • Nanotechnology/Materials / Synthetic organic chemistry

  • Nanotechnology/Materials / Bio chemistry

  • Life Science / Bioorganic chemistry

  • Life Science / Pharmaceutical chemistry and drug development sciences

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Research Keywords 【 Display / hide 】

  • 新反応開発

  • 全合成

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Research Themes 【 Display / hide 】

  • 新規複素環合成法の開発, 

    2020
    -
    Present

  • 天然有機化合物の全合成, 

    2016
    -
    Present

  • 可視光を駆動力とする有機化学反応の開発, 

    2016
    -
    Present

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Proposed Theme of Joint Research 【 Display / hide 】

  • 生物活性化合物の探索

    Interested in joint research with industry (including private organizations, etc.),  Desired form： Technical Consultation, Funded Research

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Books 【 Display / hide 】

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Papers 【 Display / hide 】

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

    Ken-ichi Takao, Satoshi Nanataki, Daisuke Aoki, Hayato Onozawa, Takashi Akiya, Genki Okuyama, Kohei Abo, Keisuke Yoshida, Akihiro Ogura

    Synlett 36 ( 10 ) 1375 - 1378 2025.03

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  0936-5214

    　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.

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

    Daiki Oka, Tomomi Ohtsuka, Ken‐ichi Takao, Akihiro Ogura

    Advanced Synthesis & Catalysis 367 ( 3 )  2024.11

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  1615-4150

    　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.

  • 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 KI, Igarashi M, Simizu S

    Bioorganic & medicinal chemistry letters (Bioorganic and Medicinal Chemistry Letters)  104   129713 - 129713 2024.03

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  0960-894X

    　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.

  • Synthesis of Indoles via Sigmatropic Rearrangements and Olefin Isomerization

    Tomoki Uchida, Ryosuke Saito, Ken‐ichi Takao, Akihiro Ogura

    Advanced Synthesis & Catalysis (Advanced Synthesis and Catalysis)  366 ( 3 ) 465 - 472 2024.02

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  1615-4150

    　View Summary

    Indoles are important heterocycles in pharmaceuticals and agrochemicals, and their atom-economical synthesis is needed. Herein, we describe the synthesis of indoles using sigmatropic rearrangements. The N-allylaniline was oxidized by environmentally benign hydrogen peroxide, and spontaneous [2,3]-Meisenheimer rearrangement gave N-allyloxyaniline. Subsequent treatment with a ruthenium catalyst afforded N-vinyloxyaniline, which underwent [3,3]-sigmatropic rearrangement to give indoles, expelling water as the only byproduct. The whole sequence is free of quantitative salt byproducts, thereby avoiding aqueous work up and cutting off the inorganic waste.

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

    Yukino Ochi, Ayano Otani, Rika Katakami, Akihiro Ogura, Ken-ichi Takao, Yoshiki Iso, Tetsuhiko Isobe

    Journal of Materials Chemistry C (Journal of Materials Chemistry C)  12 ( 18 ) 6548 - 6558 2024

    Research paper (scientific journal), Joint Work, Accepted,  ISSN  2050-7526

    　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.

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

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Reviews, Commentaries, etc. 【 Display / hide 】

  • 可視光照射で進行するBirch還元

    小椋　章弘

    月刊化学 (化学同人)  75 ( 12 ) 60 - 61 2020.12

    Single Work, Lead author, Last author, Corresponding author

  • The Stereoselective Construction of All-Carbon Quaternary Stereocenters by Allylations and Its Application to Synthetic Studies of Natural Products

    Akihiro Sakama, Akihiro Ogura, Keisuke Yoshida, Ken-ichi Takao

    Journal of Synthetic Organic Chemistry, Japan (The Society of Synthetic Organic Chemistry, Japan)  78 ( 11 ) 1039 - 1047 2020.11

    Article, review, commentary, editorial, etc. (scientific journal), Joint Work,  ISSN  0037-9980

  • Total Synthesis of Natural Products Using Intramolecular Nozaki–Hiyama–Takai–Kishi Reactions

    Ken-ichi Takao, Akihiro Ogura, Keisuke Yoshida, Siro Simizu

    Synlett (Georg Thieme Verlag {KG})  31 ( 05 ) 421 - 433 2020.02

    Article, review, commentary, editorial, etc. (scientific journal), Joint Work,  ISSN  0936-5214

    　View Summary

    In this Account, we describe our studies on the total synthesis of several natural products using intramolecular Nozaki–Hiyama–Takai–Kishi (NHTK) reactions. In each synthesis, an NHTK reaction is used to efficiently construct a medium-sized ring. These examples demonstrate the utility of the intramolecular NHTK reaction in natural product synthesis.

    1 Introduction

    2 Total Synthesis of (+)-Pestalotiopsin A

    3 Total Synthesis of (+)-Cytosporolide A

    4 Total Synthesis of (+)-Vibsanin A

    5 Total Syntheses of (+)-Aquatolide and Related Humulanolides

    6 Conclusion

  • Recent Advances in the Total Synthesis of Clavilactones

    Ken-ichi Takao, Akihiro Ogura

    HETEROCYCLES (Japan Institute of Heterocyclic Chemistry)  100 ( 9 ) 1355 - 1355 2020

    Article, review, commentary, editorial, etc. (scientific journal), Joint Work,  ISSN  0385-5414

  • Next-generation glycocluster for achieving pattern recognition in living system

    Akihiro Ogura, Katsunori Tanaka

    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN (SOC SYNTHETIC ORGANIC CHEM JPN)  77 ( 2 ) 163 - 172 2019.02

    Article, review, commentary, editorial, etc. (scientific journal), Joint Work, Lead author,  ISSN  1883-6526

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Presentations 【 Display / hide 】

  • Synthetic Studies of Callophycoic Acid A

    Kotaro Taniguchi, Akihiro Ogura, Ken-ichi Takao

    [International presentation]  The 5th International Symposium on Process Chemistry (浜松) , 

    2026.07
    , 

    Poster presentation

  • Synthesis of Indoles via Aza-oxa-Cope Rearrangement

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

    [International presentation]  The 5th International Symposium on Process Chemistry (浜松) , 

    2026.07
    , 

    Poster presentation

  • ステルヒルスチン類の全合成研究

    松原 悠太、小椋 章弘、高尾 賢一

    [Domestic presentation]  第90回有機合成化学協会関東支部シンポジウム (横浜) , 

    2026.05
    , 

    Oral presentation (general)

  • アザーオキサCope転位による3-セレニル-2-ビニルインドールの合成

    宮澤 優輔、斉藤 綾佑、大塚 友美、高尾 賢一、小椋 章弘

    [Domestic presentation]  第90回有機合成化学協会関東支部シンポジウム (横浜) , 

    2026.05
    , 

    Oral presentation (general)

  • 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) , 

    2026.03
    , 

    Oral presentation (general)

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

  • 水のみを副生成物とするインドール合成による低副作用生体内合成化学治療

    2024.04
    -
    2025.03

    Research grant, Principal investigator

  • High atom-economy low-waste synthesis of heterocycles via [2,3]-sigmatropic rearrangement

    2023.04
    -
    2024.03

    Fujimori Science and Technology Foundation, 2023年度研究助成, Research grant, Principal investigator

  • One-pot synthesis of complex structure by wavelength-selective visible light-mediated reactions

    2022.04
    -
    2025.03

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

    　View Summary

    Barton esters were irradiated with red light in the presence of catalyst, and various functional groups including oxygen and nitrogen were introduced. In particular, the carboxylic acid unit could be introduced, which was then subjected to blue-light-mediated reaction with iridium catalyst to achieve one-pot functionalization by using different wavelengths. One-pot red and blue light reaction was successfully applied to substrates with both a Barton ester moiety and redox-active ester moiety.
    DFT calculation, control experiments and measurement of redox potentials were conducted to elucidate the reaction mechanism.

  • Development of red light-mediated organic reactions

    2019.04
    -
    2022.03

    Japan Society for the Promotion of Science, Grants-in-Aid for Scientific Research, Ogura Akihiro, Grant-in-Aid for Early-Career Scientists, Research grant, Principal investigator

    　View Summary

    We have developed a red light-mediated Barton-McCombie reaction and related reactions. The reaction conditions requires very mild conditions, which can be characterized by a readily available catalyst, ambient temperature and red LED irradiation. Also, we achieved red ligh-mediated decarboxylative Giese reaction to realize carbon-carbon bond cleavage and formation within one operation. Elucidation of reaction mechanism was also conducted.

  • Development of red light-driven organic reactions

    2018.04
    -
    2019.03

    Tobe Maki Foundation, 平成30年度 研究助成, Research grant, Principal investigator

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Intellectual Property Rights, etc. 【 Display / hide 】

  • Albumin-sugar chain complex

    Date applied： PCT/JP2016/069438   

    Date announced： WO 2017002918 A1  2017.01 

    Patent, Joint

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Awards 【 Display / hide 】

  • Meiji Seika ファルマ研究企画賞

    2024.12

    Type of Award： Award from publisher, newspaper, foundation, etc.

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Courses Taught 【 Display / hide 】

  • ORGANIC CHEMISTRY

    2026

  • BACHELOR'S THESIS

    2026

  • FUNDAMENTAL COMPUTATION IN APPLIED CHEMISTRY

    2026

  • LABORATORIES IN BASIC CHEMISTRY

    2026

  • SEMINAR IN APPLIED CHEMISTRY

    2026

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Courses Previously Taught 【 Display / hide 】

  • 応用化学計算基礎

    慶應義塾大学

    2024.04
    -
    Present
    , 

    Spring Semester, Undergraduate (specialized), Seminar, Within own ｆaculty, 113people

  • 応用化学計算基礎

    慶應義塾大学

    2024
    -
    Present

  • 現代化学概論

    慶應義塾大学

    2023.10
    , 

    Autumn Semester, Undergraduate (liberal arts), Lecture, Within own ｆaculty, 180people

  • 有機化学

    慶應義塾大学

    2022.04
    -
    Present
    , 

    Spring Semester, Undergraduate (specialized), Lecture, Within own ｆaculty, 116people

  • 有機化学

    慶應義塾大学

    2022
    -
    Present

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Academic Activities 【 Display / hide 】

  • The 5th International Symposium on Process Chemistry

    2026.07

    　View Summary

    Chair for invited lecture by Prof. Thomas Wirth

  • 日本化学会第106春季年会

    2026.03

    　View Summary

    H933-1am座長

  • 第58回天然物化学談話会

    2025.07

    　View Summary

    招待講演座長

  • 日本化学会第105春季年会

    2025.03

    　View Summary

    座長

  • 日本化学会第104春季年会

    2024.03

    　View Summary

    座長

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Memberships in Academic Societies 【 Display / hide 】

  • 日本プロセス化学会, 

    2023.06
    -
    Present

  • 日本プロセス化学会, 

    2023.06

  • 日本化学会, 

    2013.11
    -
    Present

  • 日本糖質学会, 

    2013.08
    -
    2017.06

  • 日本薬学会, 

    2009.02
    -
    Present

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Committee Experiences 【 Display / hide 】

  • 2026.04
    -
    2027.09

    Steering Committee, ISCNP33-ICOB13

    　View Remarks

    Web担当

  • 2025.03
    -
    Present

    幹事, 日本化学会関東支部

  • 2025
    -
    Present

    幹事, 日本化学会関東支部

  • 2023.03
    -
    Present

    将来計画委員, 日本プロセス化学会

  • 2023
    -
    Present

    将来計画委員, 日本プロセス化学会

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