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Short total synthesis of prostaglandin

Research Project

Project/Area Number 25620074
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionTohoku University

Principal Investigator

Hayashi Yujiro  東北大学, 理学(系)研究科(研究院), 教授 (00198863)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2014: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords有機触媒 / 全合成 / 不斉触媒 / プロスタグランジン / 有機合成 / 不斉合成 / 天然物合成
Outline of Final Research Achievements

Prostaglandins regulate a broad range of physiological activities and some of their derivatives are used as effective drugs, but previously their preparation has required many operations. In the present investigation, we developed formal 3+2 cycloaddition reaction, which proceeds between succinaldehyde and nitroalkene catalyzed by diphenylprolinol silyl ether, which has been developed in my group, to afford substituted cyclopentanecarbaldehyde with excellent diastereo- and enantioselectivity. Using this reaction as a ley step, we established one of the shortest and highest-yielding asymmetric total syntheses of prostaglandin A1 and E1 methyl ester in a small number of synthetic operations using only three pots via an environmentally-benign process. Newly-developed organocatalysis technology and practical, single-pot operations involving several successive reactions produce PGA1 and PGE1 efficiently.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (12 results)

All 2015 2014 2013 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 1 results) Presentation (9 results)

  • [Journal Article] Asymmetric Formal [3+2] Cycloaddition Reaction of Succinaldehyde and Nitro­alkene Catalyzed by Diphenylprolinol Silyl Ether2015

    • Author(s)
      S. Umemiya, Y. Hayashi
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 20 Issue: 20 Pages: 4320-4324

    • DOI

      10.1002/ejoc.201500623

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nef Reaction with Molecular Oxygen in the Absence of Metal Additives, and Mechanistic Insights2014

    • Author(s)
      Shigenobu Umemiya, Kentaro Nishino, Itaru Sato, Yujiro Hayashi
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Issue: 48 Pages: 15753-15759

    • DOI

      10.1002/chem.201403475

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Asymmetric Mannich Reaction of α-Keto Imines Catalyzed by Diarylprolinol Silyl Ether2013

    • Author(s)
      Y. Hayashi, D. Sakamoto, H. Shomura, D. Hashizume
    • Journal Title

      Chem. Eur. J.

      Volume: 19 Issue: 12 Pages: 7678-7681

    • DOI

      10.1002/anie.201209380

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] プロスタグランジン類の合成研究2015

    • Author(s)
      梅宮茂伸、坂本大輔、林雄二郎
    • Organizer
      第32回有機合成化学セミナー
    • Place of Presentation
      ニューウェルシティ湯河原
    • Year and Date
      2015-09-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] Total Synthesis of Prostaglandin E1 Methyl Ester by Three One-pot Operations2015

    • Author(s)
      Y. Hayashi, S. Umemiya
    • Organizer
      The 3rd International Symposium of Process Chemistry
    • Place of Presentation
      Kyoto International Conference Center, Kyoto
    • Year and Date
      2015-07-14
    • Related Report
      2015 Annual Research Report
  • [Presentation] ジフェニルプロリノールシリルエーテル触媒を用いる形式的不斉[3+2]付加環化反応2015

    • Author(s)
      梅宮茂伸、河内元希、林雄二郎
    • Organizer
      モレキュラー・キラリティー2015
    • Place of Presentation
      早稲田大学 西早稲田キャンパス
    • Year and Date
      2015-06-12
    • Related Report
      2015 Annual Research Report
  • [Presentation] 酸素を用いるNef反応の開発と反応機構解析2015

    • Author(s)
      梅宮茂伸、西野健太郎、佐藤格、林雄二郎
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部
    • Year and Date
      2015-03-26
    • Related Report
      2014 Research-status Report
  • [Presentation] 酸素を用いるNef反応の開発とプロスタグランジン合成への応用2014

    • Author(s)
      梅宮茂伸、西野健太郎、佐藤格、林雄二郎
    • Organizer
      第106回有機合成シンポジウム
    • Place of Presentation
      早稲田大学国際会議場
    • Year and Date
      2014-11-06 – 2014-11-07
    • Related Report
      2014 Research-status Report
  • [Presentation] プロスタグランジンE1メチルエステルの3ポット合成

    • Author(s)
      梅宮茂伸、林雄二郎
    • Organizer
      第24回 万有仙台シンポジウム
    • Place of Presentation
      仙台国際センター
    • Related Report
      2013 Research-status Report
  • [Presentation] プロスタグランジンE1メチルエステルの3ポット合成

    • Author(s)
      梅宮茂伸、林雄二郎
    • Organizer
      第55回天然有機化合物討論会
    • Place of Presentation
      同志社大学・寒梅館
    • Related Report
      2013 Research-status Report
  • [Presentation] Total Synthesis of Prostaglandin E1 Methyl Ester by Three One-pot Operations

    • Author(s)
      Shigenobu Umemiya, Yujiro Hayashi
    • Organizer
      第13回国際抗生物質関連化学会議
    • Place of Presentation
      富士ビューホテル
    • Related Report
      2013 Research-status Report
  • [Presentation] Concise Total Synthesis of Prostaglandin E1 Methyl Ester

    • Author(s)
      Shigenobu Umemiya, Yujiro Hayashi
    • Organizer
      平成25年度化学系学協会東北大会及び日本化学会東北支部70周年記念国際会議
    • Place of Presentation
      東北大学・川内キャンパス
    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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