OGURA Akihiro

写真a

Affiliation

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

Position

Assistant Professor/Senior Assistant Professor

Related Websites

External Links
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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, Biofunctional Synthetic Chemistry Laboratory, Postdoctoral Associate

  • 2016.04
    -
    2019.03

    Keio University, Department of Applied Chemistry, Faculty of Science and Technology, Research Associate

  • 2019.04
    -
    2021.03

    Keio University, Department of Applied Chemistry, Faculty of Science and Technology, Research Associate

  • 2021.04
    -
    Present

    Keio University, Department of Applied Chemistry, Faculty of Science and Technology, Senior Assistant Professor

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Academic Background 【 Display / hide 】

  • 2004.04
    -
    2008.03

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

    University, Graduated, Other

  • 2008.04
    -
    2010.03

    The University of Tokyo, Graduate School of Pharmaceutical Sciences, Division of Pharmaceutical Chemistry

    Graduate School, Completed, Master's course

  • 2010.04
    -
    2013.03

    The University of Tokyo, Graduate School of Pharmaceutical Sciences, Division of Pharmaceutical Chemistry

    Graduate School, Completed, Doctoral course

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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

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

    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

    Oka, D; Ohtsuka, T; Takao, KI; Ogura, A

    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

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

    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 】

  • 連続的渡環ラジカル環化反応を鍵としたステルヒルスチン類の全合成研究

    松原 悠太, 南 友紀子, 小椋 章弘, 高尾 賢一

    第88回有機合成化学協会関東支部シンポジウム (東京) , 

    2025.05
    , 

    Oral presentation (general)

  • 生体内インドール合成に向けた人工金属酵素およびインドール骨格を有する生物活性物質の合成研究

    雨宮 司, 関 健太, 高尾 賢一, Tsung-che Chang, 田中 克典, 小椋 章弘

    日本化学会第105春季年会 (吹田) , 

    2025.03
    , 

    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

    大塚 友美, 岡 大輝, 高尾 賢一, 小椋 章弘

    日本化学会第105春季年会 (吹田) , 

    2025.03
    , 

    Oral presentation (general)

  • Synthesis of Indoles via Sigmatropic Rearrangements

    Akihiro Ogura

    17th Yonsei CECS-Keio LCC Joint Symposium (Seoul, Korea) , 

    2024.11
    , 

    Oral presentation (invited, special)

  • ステルヒルスチンAおよびBの全合成研究

    南 友紀子 野村 亮太, 小椋 章弘, 高尾 賢一

    第66回天然有機化合物討論会 (京都) , 

    2024.09
    , 

    Poster presentation

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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

  • 可視光の波長制御による複雑骨格のワンポット構築法の開発

    2022.04
    -
    2025.03

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

    　View Summary

    赤色光は低コストや高エネルギー変換効率、安全性といった明確な利点を有するにもかかわらず、その有機合成化学における利用は見過ごされてきた。本研究では、注目されてこなかったこの未開拓のエネルギー源である赤色光の可能性を最大限引き出し、真に持続可能な社会にふさわしい反応の開発を目指すため、青色光との波長選択的なラジカル反応を実現する。具体的には、赤色光を用いたBarton脱炭酸的官能基化反応の開発、赤色光→青色光の照射によるワンポットでの炭素-炭素結合の自在な生成と切断に取り組み、最終的にはこれらを光フロー反応に展開する。

  • 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 】

  • FUNDAMENTAL COMPUTATION IN APPLIED CHEMISTRY

    2025, Spring Semester, Undergraduate (specialized), Seminar, Within own ｆaculty

  • LABORATORIES IN APPLIED CHEMISTRY B

    2025, Spring Semester, Undergraduate (specialized), Laboratory work/practical work/exercise, Within own ｆaculty

  • LABORATORIES IN BASIC CHEMISTRY

    2025, Autumn Semester, Undergraduate (specialized), Laboratory work/practical work/exercise, Within own ｆaculty

  • ORGANIC CHEMISTRY

    2025, Spring Semester, Undergraduate (specialized), Lecture, Within own ｆaculty

  • SEMINAR IN APPLIED CHEMISTRY

    2025, Full academic year, Undergraduate (specialized), Lecture, Within own ｆaculty

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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

  • 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

  • 応用化学輪講

    慶應義塾大学

    2021.04
    -
    Present
    , 

    Full academic year, Undergraduate (specialized), Lecture, Within own ｆaculty, 7people

  • 卒業研究

    慶應義塾大学

    2021.04
    -
    Present
    , 

    Full academic year, Undergraduate (specialized), Lecture, Within own ｆaculty, 7people

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Academic Activities 【 Display / hide 】

  • 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

  • 日本化学会第104春季年会

    2024.03

    　View Summary

    座長

  • 第56回天然物化学談話会　奨励賞受賞講演

    2023.06

    　View Summary

    座長

  • 日本化学会第103春季年会

    2023.03

    　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

  • 日本化学会, 

    2013.11
    -
    Present

  • 日本薬学会, 

    2009.02
    -
    Present

  • 有機合成化学協会, 

    2007.05
    -
    Present
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Committee Experiences 【 Display / hide 】

  • 2025.03
    -
    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

  • 2019.09
    -
    2020.12

    プログラム編成小委員会, 日本化学会

  • 2018.12
    -
    2019.05

    第77回関東支部シンポジウム実行委員会, 有機合成化学協会

  • 2017.09
    -
    Present

    世話人, 天然物談話会

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