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

Profile 【 Display / hide

  • 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)

Career 【 Display / hide

  • 2010.04
    -
    2013.03

    JSPS, Research Fellow (DC1)

  • 2013.04
    -
    2016.03

    RIKEN, Biofunctional Synthetic Chemistry Laboratory, Postdoctoral Associate

  • 2016.04
    -
    Present

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

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

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

 

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

 

Papers 【 Display / hide

  • 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)   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

    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.

  • Red-light-mediated BartonMcCombie reaction

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

    Bulletin of the Chemical Society of Japan (Bulletin of the Chemical Society of Japan)  93 ( 7 ) 936 - 941 2020.07

    ISSN  00092673

     View Summary

    A red-light-mediated BartonMcCombie reaction is described, in which chlorophyll a is used as a photocatalyst and tris(trimethylsilyl)silane or Hantzsch ester is used as the hydrogen source. The reaction can be performed with a set of easily available equipment and reagents, and a variety of linear and cyclic xanthates could be applied. In contrast to the traditional conditions, the reaction does not involve toxic organotin or an explosive radical initiator. The reaction mechanism was analyzed both by experiments and computation, and it was suggested that the radical chain mechanism initiated by excitation of complex followed by charge transfer is likely to be operative.

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Presentations 【 Display / hide

  • 赤色LEDを用いたBarton-MacCombie反応の開発

    第113回有機合成シンポジウム, 

    2018.06

    Poster presentation

  • ミスラミンの不斉全合成

    第75回有機合成化学協会関東支部シンポジウム, 

    2018.05

    Oral presentation (general)

  • ステルヒルスチンAのヒルスタン型セスキテルペン部の合成研究

    日本化学会第98春季年会, 

    2018.03

    Oral presentation (general)

  • ビブサニンBの全合成研究

    日本化学会第98春季年会, 

    2018.03

    Oral presentation (general)

  • ゼイラニジンの全合成研究

    日本化学会第98春季年会, 

    2018.03

    Oral presentation (general)

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

  • 赤色光を用いた有機化学反応の開発

    2019.04
    -
    2021.03

    日本学術振興会, 科学研究費助成事業, 若手研究, Research grant, Principal investigator

     View Summary

    本研究においてはエネルギー変換効率や安全性に優れた赤色LEDをエネルギー源として用いた、新しい有機化学反応の開発を行う。有機化合物の骨格をなす炭素-炭素結合の生成のみならず、これを切断したり、酸素など他の原子の着脱を赤色光をエネルギー源として自在に行うことを目指す。

  • Controlling protein/cell biofunction by chemical introduction of glycans

    2014.04
    -
    2017.03

    MEXT,JSPS, Grant-in-Aid for Scientific Research, Grant-in-Aid for Challenging Exploratory Research, Principal investigator

     View Summary

    We have developed an efficient strategy for synthesis of artificial glycoprotein. This strategy provides the target molecule just by mixing the reagent under mild conditions and does not need prior genetic modification. The glycoproteins thus synthesized were injected to mice and their in vivo kinetics was analyzed. It was revealed that excretion pathway could be controlled and cell selective accumulation was achieved depending on the glycan structure on the protein. Furthermore, first organ-selective metal-catalyzed organic reaction was realized by attaching metal catalyst onto this artificial glycoprotein.

 

Courses Taught 【 Display / hide

  • SEMINAR IN APPLIED CHEMISTRY

    2022

  • ORGANIC CHEMISTRY

    2022

  • LABORATORIES IN BASIC CHEMISTRY

    2022

  • LABORATORIES IN APPLIED CHEMISTRY B

    2022

  • BACHELOR'S THESIS

    2022

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Courses Previously Taught 【 Display / hide

  • 基礎化学実験

    Keio University

    2017.04
    -
    2018.03

    Autumn Semester, Laboratory work/practical work/exercise, Lecturer outside of Keio

  • 応用化学実験B

    Keio University

    2017.04
    -
    2018.03

    Spring Semester, Laboratory work/practical work/exercise, Lecturer outside of Keio

 

Memberships in Academic Societies 【 Display / hide

  • 日本化学会

     
  • 有機合成化学協会

     
  • 日本薬学会

     

Committee Experiences 【 Display / hide

  • 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

  • 2016.11
    -
    Present

    実行委員, 慶應有機化学若手シンポジウム実行委員会

  • 2016.06
    -
    2017.03

    第97春季年会 会場総務委員, 日本化学会