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Development of Method for Molecular Transformations Based on Photoredox Reaction of Quinones

Research Project

Project/Area Number 26810018
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

ANDO Yoshio  東京工業大学, 理学院, 助教 (40532742)

Project Period (FY) 2014-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2016: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2015: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords有機合成化学 / キノン / 光化学反応 / 天然物 / 全合成 / ナフトキノン / CH官能基化 / 酸化還元 / 立体特異的合成
Outline of Final Research Achievements

Quinones are widely distributed in nature as pigments and bioactive molecules. Some quinones show particular reactivity under photo-irradiation. However, such reactivity has been overlooked and not been employed in organic synthesis so far.
In this research, a new synthetic method for organic compounds, which have been unachievable by conventional method, was developed by exploiting photoredox reaction of quinones. The substrate scope has been clarified. Moreover, it was found that the photoredox reaction proceeds with stereospecific manner. As the application, the first enantioselective total synthesis of spiroxin C, dimerized naphthoquinone natural product, has been accomplished by employing stereospecific photoredox reaction as the key step.

Report

(5 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • 2014 Research-status Report
  • Research Products

    (20 results)

All 2018 2017 2016 2015 Other

All Journal Article (2 results) (of which Peer Reviewed: 2 results) Presentation (16 results) (of which Int'l Joint Research: 5 results,  Invited: 4 results) Remarks (2 results)

  • [Journal Article] Intramolecular Photoredox Reaction of Naphthoquinone Derivatives2017

    • Author(s)
      Yoshio Ando, Takashi Matsumoto, Keisuke Suzuki
    • Journal Title

      Synlett

      Volume: 28 Issue: 09 Pages: 1040-1045

    • DOI

      10.1055/s-0036-1589001

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereospecificity in Intramolecular Photoredox Reactions of Naphthoquinones: Enantioselective Total Synthesis of (-)-Spiroxin C2017

    • Author(s)
      Yoshio Ando, Atsuko Hanaki, Ryota Sasaki, Ken Ohmori, Keisuke Suzuki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 56 Issue: 38 Pages: 11460-11465

    • DOI

      10.1002/anie.201705562

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Presentation] 連続的酸化還元反応を鍵とするスピロキシンAの全合成研究2018

    • Author(s)
      安藤吉勇、佐々木亮太、大森建、鈴木啓介
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] スピロキシンAの合成研究:合成中間体の保護基の検討2018

    • Author(s)
      田中大裕、佐々木亮太、安藤吉勇、大森建、鈴木啓介
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 分子内光酸化還元反応を鍵とするγ-ルブロマイシンの全合成研究2017

    • Author(s)
      脇田 文博、安藤 吉勇、大森 建、鈴木 啓介
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      慶應義塾大学日吉キャンパス (横浜)
    • Year and Date
      2017-03-18
    • Related Report
      2016 Research-status Report
  • [Presentation] Total synthesis of γ-rubromycin by exploiting intramolecular photoredox reaction2017

    • Author(s)
      Fumihiro Wakita, Yoshio Ando, Ken Ohmori, Keisuke Suzuki
    • Organizer
      10th Workshop on Organic Chemistry for Junior Chemist (WOCJC-10)
    • Place of Presentation
      National Tsing Ua University (Hsinchu, Taiwan
    • Year and Date
      2017-01-06
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Stereospecificity in Intramolecular Photoredox Reactions of Naphthoquinones: Enantioselective Total Synthesis of (-)-Spiroxin C2017

    • Author(s)
      Yoshio Ando, Atsuko Hanaki, Ryota Sasaki, Takashi Matsumoto, Ken Ohmori, Keisuke Suzuki
    • Organizer
      The 26th International Society of Heterocyclic Chemistry (26th ISHC Congress)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Redox Reaction of Naphthoquinones: Total Syntheses of Spiroxin C and Engelharquinone2016

    • Author(s)
      Yoshio Ando
    • Organizer
      ACP Lecureship Tour in China
    • Place of Presentation
      Shaanxi Normal University, (Xi’an, China)
    • Year and Date
      2016-11-10
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Redox Reaction of Naphthoquinones: Total Syntheses of Spiroxin C and Engelharquinone2016

    • Author(s)
      Yoshio Ando
    • Organizer
      ACP Lecureship Tour in China
    • Place of Presentation
      Lanzhou University, (Lanzhou, China)
    • Year and Date
      2016-11-08
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] 1,2-ナフトキノン誘導体を用いた分子内光酸化還元反応の開発研究2016

    • Author(s)
      脇田 文博、安藤 吉勇、大森 建、鈴木 啓介
    • Organizer
      第109回有機合成シンポジウム
    • Place of Presentation
      東京工業大学大岡山キャンパス (東京)
    • Year and Date
      2016-06-08
    • Related Report
      2016 Research-status Report
  • [Presentation] ナフトキノンの特異な反応性を活用した天然物合成2016

    • Author(s)
      安藤 吉勇
    • Organizer
      第4回慶應有機化学若手シンポジウム
    • Place of Presentation
      慶應義塾大学矢上キャンパス (横浜)
    • Year and Date
      2016-05-07
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] 1,2-ナフトキノン誘導体の分子内酸化還元反応2016

    • Author(s)
      脇田文博、安藤吉勇、大森建、鈴木啓介
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス (京都府)
    • Year and Date
      2016-03-26
    • Related Report
      2015 Research-status Report
  • [Presentation] スピロキシンAの全合成研究2016

    • Author(s)
      佐々木亮太、安藤吉勇、大森建、鈴木啓介
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学京田辺キャンパス (京都府)
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] ナフトキノン類の酸化還元能を活用した分子変換法の開発と天然物合成への応用2015

    • Author(s)
      安藤 吉勇
    • Organizer
      第39回星薬科大学大学院研究科助手会・大学院自治会 合同公開セミナー
    • Place of Presentation
      星薬科大学 医薬品化学研究所 5F 大谷ホール (東京都)
    • Year and Date
      2015-11-07
    • Related Report
      2015 Research-status Report
    • Invited
  • [Presentation] Total Synthesis of (-)-spiroxin C2015

    • Author(s)
      Yoshio Ando, Atsuko Hanaki, Ryota Sasaki, Takashi Matsumoto, Ken Ohmori, Keisuke Suzuki
    • Organizer
      ICCEOCA-10
    • Place of Presentation
      85 Sky Tower Hotel, Kaohsiung, Taiwan
    • Year and Date
      2015-11-04
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] ナフトキノンの立体特異的な光酸化還元反応:スピロキシン類の不斉全合成2015

    • Author(s)
      安藤吉勇、花木淳子、佐々木亮太、松本隆司、大森建、鈴木啓介
    • Organizer
      第57回天然有機化合物討論会
    • Place of Presentation
      神奈川県民ホール (神奈川県)
    • Year and Date
      2015-09-10
    • Related Report
      2015 Research-status Report
  • [Presentation] (-)-スピロキシンCの全合成研究2015

    • Author(s)
      安藤吉勇、花木淳子、大森建、鈴木啓介
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] スピロキシンAの合成研究2015

    • Author(s)
      佐々木亮太、安藤吉勇、大森建、鈴木啓介
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2015-03-28
    • Related Report
      2014 Research-status Report
  • [Remarks] Suzuki-Ohmori research group

    • URL

      http://www.org-synth.chem.sci.titech.ac.jp/suzukilab/

    • Related Report
      2017 Annual Research Report
  • [Remarks] Suzuki–Ohmori Research Group

    • URL

      http://www.org-synth.chem.sci.titech.ac.jp/suzukilab/

    • Related Report
      2016 Research-status Report

URL: 

Published: 2014-04-04   Modified: 2019-03-29  

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