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Synthesis of macrocyclic natural products

Research Project

Project/Area Number 15K05493
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionIbaraki University

Principal Investigator

Sato Itaru  茨城大学, 理工学研究科(理学野), 教授 (80318196)

Project Period (FY) 2015-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2018: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2017: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Keywords天然物合成 / 有機合成化学 / ウスチロキシン / アリールエーテル形成 / ガレオン / 全合成 / 生理活性天然物 / アリールエーテル / 生理活性化合物
Outline of Final Research Achievements

Convenient and reliable method for aryl ether formation was developed. By using this methodology, a macrocyclic bioactive natural product, ustiloxin D was successfully synthesized .

Academic Significance and Societal Importance of the Research Achievements

医薬として臨床に用いられているタキソールと同様,有糸分裂阻害剤活性を有する環状ペプチドであるウスチロキシンの全合成は医薬のリード化合物の合成として社会的意義を有する。またこの合成の過程で明らかにすることができた充分に温和な条件下でのアリールエーテル形成法の確立は,多官能基性の天然物合成を行う上で問題となるアリールエーテル形成を,合成の最初ではなく最終段階に行うことを可能にしたものであり,学術的にも重要な意義を持つ

Report

(5 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • 2015 Research-status Report

Research Products

(14 results)

All 2018 2017 2016 2015

All Journal Article Presentation Book

  • [Journal Article] Prolinate Salt as a Catalyst in the syn-Selective, Asymmetric Mannich Reaction of Alkynyl Imine2018

    • Author(s)
      Hayashi Yujiro、Yamazaki Tatsuya、Kawauchi Genki、Sato Itaru
    • Journal Title

      Organic Letters

      Volume: 20 Pages: 2391-2394

    • DOI

      10.1021/acs.orglett.8b00728

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Two-Pot Synthesis of Chiral 1,3-syn-Diols through Asymmetric Organocatalytic Aldol and Wittig Reactions Followed by Domino Hemiacetal/Oxy-Michael Reactions2018

    • Author(s)
      Hayashi Yujiro、Saitoh Takanobu、Arase Hiromu、Kawauchi Genki、Takeda Naohiro、Shimasaki Yasuharu、Sato Itaru
    • Journal Title

      Chemistry - A European Journal

      Volume: 24 Pages: 4909-4915

    • DOI

      10.1002/chem.201705930

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Prolinate Salt as a Catalyst in the syn-Selective, Asymmetric Mannich Reaction of Alkynyl Imine2018

    • Author(s)
      Hayashi, Yujiro; Yamazaki, Tatsuya; Kawauchi, Genki; Sato, Itaru
    • Journal Title

      Org. Lett.

      Volume: 20 Pages: 2391-2394

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Two-Pot Synthesis of Chiral 1,3-syn-Diols through Asymmetric Organocatalytic Aldol and Wittig Reactions Followed by Domino Hemiacetal/Oxy-Michael Reactions2018

    • Author(s)
      Hayashi, Yujiro; Saitoh, Takanobu; Arase, Hiromu; Kawauchi, Genki; Takeda, Naohiro; Shimasaki, Yasuharu; Sato, Itaru
    • Journal Title

      Chem. Eur. J

      Volume: 24 Pages: 4909-4915

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Point-to-point ultra-remote asymmetric control with flexible linker2017

    • Author(s)
      T. Kawasaki, Y. Ishikawa, Y. Minato, T. Otsuka, S. Yonekubo, I. Sato, T. Shibata, A. Matsumoto, K. Soai
    • Journal Title

      Chemistry A European Journal

      Volume: 23 Pages: 282-285

    • DOI

      10.1002/chem.201605076

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Thermodynamics of Complexation between Thiourea-based Receptor and Acetate in Water/Acetonitrile Mixture2016

    • Author(s)
      Takaya Suzuki, Yuuta Shibuya, Takaya Sato, Seiichi Nishizawa, Itaru Sato, Akira Yamaguchi
    • Journal Title

      Anal. Sci.

      Volume: 32 Issue: 7 Pages: 741-744

    • DOI

      10.2116/analsci.32.741

    • NAID

      130005163085

    • ISSN
      0910-6340, 1348-2246
    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Oxidative Amidation of Nitroalkanes with Amine Nucleophiles using Molecular Oxygen and Iodine2015

    • Author(s)
      Jing Li, Martin J. Lear, Yuya Kawamoto, Shigenobu Umemiya, Alice R. Wong, Eunsang Kwon, Itaru Sato, Yujiro Hayashi
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 53 Pages: 12986-12990

    • DOI

      10.1002/anie.201505192

    • Related Report
      2015 Research-status Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Aldol Reaction of α,α-Disubstituted Acetaldehydes Catalyzed by Diphenylprolinol Silyl Ether for the Construction of Quaternary Stereogenic Centers2015

    • Author(s)
      Yujiro Hayashi, Hiroki Shomura, Qianqian Xu, Martin J. Lear, Itaru Sato
    • Journal Title

      Eur. J. Org. Chem

      Volume: 2015 Pages: 4316-4319

    • DOI

      10.1002/ejoc.201500585

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] トリビニルビスマスをビニル化剤とするフェノール類のO-ビニル化反応2018

    • Author(s)
      安部 侑央・岩上 由姫・佐藤 格
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 環状ジアリールエーテルヘプタノイド(+)-メチルガレオンのエナンチオ選択的全合成2018

    • Author(s)
      鈴木 華子・藤田 圭一郎・佐藤 格
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 光学活性な環状ジアリールエーテルヘプタノイド(+)-methylgaleonの合成研究2017

    • Author(s)
      鈴木 華子・藤田 圭一郎・佐藤 格
    • Organizer
      第28回日本化学会関東支部茨城地区研究交流会
    • Related Report
      2017 Research-status Report
  • [Presentation] トリビニルビスマスを用いたフェノール類のO-ビニル化2017

    • Author(s)
      安部 侑央・佐藤 格
    • Organizer
      第28回日本化学会関東支部茨城地区研究交流会
    • Related Report
      2017 Research-status Report
  • [Presentation] Ustiloxin Dの全合成研究2017

    • Author(s)
      五頭 史泰・佐藤 格
    • Organizer
      第28回日本化学会関東支部茨城地区研究交流会
    • Related Report
      2017 Research-status Report
  • [Book] Synthesis of Pyrimidine-terminated Chiral Large Molecular Architectures with Functions of Self-replication and Self-improvement by Asymmetric Autocatalysis in Advances in Asymmetric Autocatalysis and Related Topics 1st Edition2017

    • Author(s)
      Tsuneomi Kawasaki, Arimasa Matsumoto, Itaru Sato, Kenso Soai
    • Publisher
      Elsevier
    • Related Report
      2016 Research-status Report

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Published: 2015-04-16   Modified: 2020-03-30  

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