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Development of Methods for Synthesis of Aminosugars by Catalytic Asymmetric Addition Reactions of alpha-Ketoesters

Research Project

Project/Area Number 18K05123
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Review Section Basic Section 33020:Synthetic organic chemistry-related
Research InstitutionOkayama University

Principal Investigator

Sakakura Akira  岡山大学, 自然科学研究科, 教授 (80334043)

Project Period (FY) 2018-04-01 – 2021-03-31
Project Status Completed (Fiscal Year 2020)
Budget Amount *help
¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000)
Fiscal Year 2020: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2019: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2018: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Keywords不斉合成 / 不斉触媒 / 炭素-炭素結合形成反応 / アミノ糖 / ルイス酸 / ブレンステッド酸 / 触媒 / キラルルイス酸 / Mannich反応 / Diels-Alder反応 / アミノアルコール / アミノ酸 / ルイス酸触媒 / α-ケトエステル / 付加反応 / 有機分子触媒 / 不斉付加反応
Outline of Final Research Achievements

Amino sugars, which are useful antibiotics, have carbon skeleton bearing several hydroxy and amino groups. Since the structures of amino sugars are highly complex, the stereoselective synthesis of amino sugars is quite difficult. In this study, we have developed the methods of stereoselective synthesis of amino sugars by using asymmetric catalyst. As results, we succeeded to develop several enantioselective carbon-carbon bond forming reaction. In addition, we achieved formal total synthesis of manzacidin B, which have carbon skeleton bearing continuous amino and hydroxy groups.

Academic Significance and Societal Importance of the Research Achievements

アミノ糖類は,最も汎用される抗生物質の一つである。その活性は,立体化学を含む構造に大きく依存する。副作用の少ない新規アミノ糖抗生物質を開発するためには,アミノ糖類の様々な誘導体を自在に化学合成できるようにならなければならない。本研究は,様々なアミノ糖類を立体選択的に化学合成するための方法を提案するものである。本研究で開発した方法を用いれば,アミノ糖類のいくつかを立体選択的に化学合成できるため,副作用の少ない新しいアミノ糖抗生物質の開発が可能となる。

Report

(4 results)
  • 2020 Annual Research Report   Final Research Report ( PDF )
  • 2019 Research-status Report
  • 2018 Research-status Report
  • Research Products

    (10 results)

All 2021 2020 2019 Other

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (5 results) Remarks (1 results)

  • [Journal Article] Enantioselective Diels?Alder Reaction of 3-Nitrocoumarins Promoted by Chiral Organoammonium Salt Catalysts2020

    • Author(s)
      Sakakura Akira、Fujii Yudai、Nakao Ryota、Sugihara Saki、Fujita Keita、Araki Yuya、Kudoh Takayuki、Hayakawa Ichiro、Mizoguchi Haruki
    • Journal Title

      Synlett

      Volume: 31 Issue: 20 Pages: 2013-2017

    • DOI

      10.1055/s-0040-1707302

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Kinetic Resolution of α-Nitrolactones by Catalytic Asymmetric Hydrolysis or Ester-Amide Exchange Reaction2020

    • Author(s)
      Sakakura Akira、Nakao Ryota、Fujii Yudai、Hayakawa Ichiro、Mizoguchi Haruki
    • Journal Title

      Synlett

      Volume: 31 Issue: 20 Pages: 2018-2022

    • DOI

      10.1055/s-0040-1707303

    • Related Report
      2020 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Formal Total Synthesis of Manzacidin B via Sequential Diastereodivergent Henry Reaction2019

    • Author(s)
      Araki Yuya、Miyoshi Natsumi、Morimoto Kazuki、Kudoh Takayuki、Mizoguchi Haruki、Sakakura Akira
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 85 Issue: 2 Pages: 798-805

    • DOI

      10.1021/acs.joc.9b02811

    • NAID

      120006948961

    • Related Report
      2019 Research-status Report
    • Peer Reviewed
  • [Journal Article] Catalytic enantioselective Hosomi-Sakurai reaction of α-ketoesters promoted by chiral copper(II) complexes2019

    • Author(s)
      Yutaro Niwa, Mayu Miyake, Ichiro Hayakawa, Akira Sakakura
    • Journal Title

      Chemical Communications

      Volume: 55 Issue: 27 Pages: 3923-3926

    • DOI

      10.1039/c9cc01159e

    • NAID

      120006823173

    • Related Report
      2018 Research-status Report
    • Peer Reviewed
  • [Presentation] キラル有機アンモニウム塩触媒を用いた3-ニトロクマリンのエナンチオ選択的Diels-Alder反応2021

    • Author(s)
      藤田 啓太、杉原 早紀、荒木 雄也、早川 一郎、溝口 玄樹、坂倉 彰
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] α-ケトエステルの直截的不斉Mannich反応に有効なキラル銅(II)触媒の設計2021

    • Author(s)
      近藤 真由、岩木 伸穏、三宅 麻由、溝口 玄樹、坂倉 彰
    • Organizer
      日本化学会第101春季年会
    • Related Report
      2020 Annual Research Report
  • [Presentation] キラルルイス酸触媒を用いたα,α-二置換-β-ヒドロキシ-α-アミノ酸構造の立体選択的構築法の開発2020

    • Author(s)
      花田将人,荒木雄也,溝口玄樹,坂倉彰
    • Organizer
      日本化学会第100春季年会
    • Related Report
      2019 Research-status Report
  • [Presentation] ジアステレオ選択的Henry反応を鍵とするマンザシジンBの形式全合成2019

    • Author(s)
      荒木雄也,三好夏美,森本一樹,溝口玄樹,坂倉彰
    • Organizer
      第61回天然有機化合物討論会
    • Related Report
      2019 Research-status Report
  • [Presentation] キラル銅(II)触媒を用いたα-ケトエステルの直截的な不斉Mannich反応の開発2019

    • Author(s)
      三宅麻由,重森圭介,早川一郎,坂倉彰
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Research-status Report
  • [Remarks] 生物有機化学研究室

    • URL

      http://www.cc.okayama-u.ac.jp/~sakakura/bioorgchem/

    • Related Report
      2020 Annual Research Report

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Published: 2018-04-23   Modified: 2022-01-27  

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