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Controlled Synthesis and Development of Higher-order Functional Biomass Polyphenols

Research Project

Project/Area Number 16H04107
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

Ohmori Ken  東京工業大学, 理学院, 准教授 (50282819)

Research Collaborator Suzuki Keisuke  
Misaka Takumi  
Project Period (FY) 2016-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥17,030,000 (Direct Cost: ¥13,100,000、Indirect Cost: ¥3,930,000)
Fiscal Year 2018: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2017: ¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2016: ¥6,500,000 (Direct Cost: ¥5,000,000、Indirect Cost: ¥1,500,000)
Keywordsポリフェノール / 天然有機化合物 / フラボノイド / カテキン / 有機合成 / オリゴマー / オルトゴナル活性化法 / 天然物合成 / イソフラボノイド / ロテノン / デグエリン / プシラチン / フラバンオリゴマー / バイオマス
Outline of Final Research Achievements

Although natural polyphenols have long played a part in human life as ingredients of wine, tea, or herbal medicines, it was only recently that their biological functions have been unveiled at the molecular level. The realization that specific interactions of polyphenols with biomolecules, such as proteins, exert powerful biological activities has stimulated the search for new pharmaceutical entities derived from polyphenolic entities. These investigations, however, are often hampered by the difficulty in isolating the requisite compounds in pure and structurally defined form, largely because their procurement has relied on natural sources, e.g., plant extracts. This study successfully offers one of synthetic solutions to provide such compounds, in particular, doubly-linked oligomeric flavans. The present study is based on an orthogonal synthetic strategy coupled with an annulation method, enabling efficient accesses to various types of flavan oligomers.

Academic Significance and Societal Importance of the Research Achievements

本研究により、これまで入手困難であった複雑な構造を有する様々なフラバンオリゴマーの合成が自在かつ簡便にできるようになった。これにより、従来いわゆる「物質」として、ある組成を持った混合物のまま取り扱われてきたポリフェノールを、純度が高く構造の定まった標品として供給することができるようになった。今後はそれぞれの生理活性や機能評価を進めることが可能となり、これまで未知であった個々の化合物の化学的特性が分子レベルで明らかになるものと期待される。これらの成果は、従来興味を示さなかった産業界や学術領域にも多大なインパクトをもたらすものと予想される。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Annual Research Report
  • 2016 Annual Research Report
  • Research Products

    (34 results)

All 2019 2018 2017 2016

All Journal Article (7 results) (of which Peer Reviewed: 7 results,  Open Access: 1 results,  Acknowledgement Compliant: 3 results) Presentation (27 results) (of which Int'l Joint Research: 3 results,  Invited: 12 results)

  • [Journal Article] Total Synthesis of Carthamin, a Traditional Natural Red Pigment2019

    • Author(s)
      K. Azami, T. Hayashi, T. Kusumi, K. Ohmori, K. Suzuki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 58 Issue: 16 Pages: 5321-5326

    • DOI

      10.1002/anie.201900454

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] General Synthetic Approach to Rotenoids via Stereospecific, Group-Selective 1,2-Rearrangement and Dual SNAr Cyclizations of Aryl Fluorides2019

    • Author(s)
      S. Matsuoka, K. Nakamura, K. Ohmori, K. Suzuki
    • Journal Title

      Syntheis

      Volume: 51 Issue: 05 Pages: 1139-1156

    • DOI

      10.1055/s-0037-1611654

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Total Syntheses of Pusilatins A-C, Liverwort-Derived Macrocyclic Bisbibenzyl Dimers2018

    • Author(s)
      T. Yamada, H. Takiguchi, K. Ohmori, K. Suzuki
    • Journal Title

      Organic Letters

      Volume: 20 Issue: 12 Pages: 3579-3582

    • DOI

      10.1021/acs.orglett.8b01366

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Selligueain A, a Sweet Flavan Trimer2018

    • Author(s)
      Noguchi Yuka、Takeda Rikako、Suzuki Keisuke、Ohmori Ken
    • Journal Title

      Organic Letters

      Volume: 20 Issue: 10 Pages: 2857-2861

    • DOI

      10.1021/acs.orglett.8b00873

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereocontrolled Total Syntheses of (-)-Rotenone and (-)-Dalpanol by 1,2-Rearrangement and SNAr Oxycyclizations2017

    • Author(s)
      K. Nakamura, K. Ohmori, K. Suzuki
    • Journal Title

      Angewandte Chemie Int Ed

      Volume: 56 Issue: 1 Pages: 182-187

    • DOI

      10.1002/anie.201609253

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthetic Study on Carthamin. 2 Stereoselective Approach to C-Glycosyl Quinochalcone via Desymmetrization2017

    • Author(s)
      T. Hayashi, K. Ohmori, K. Suzuki
    • Journal Title

      Organic Letters

      Volume: 19 Issue: 4 Pages: 866-869

    • DOI

      10.1021/acs.orglett.6b03899

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Total Synthesis of (+)-Vicenin-22016

    • Author(s)
      T. C. Ho, K. Ohmori, K. Suzuki
    • Journal Title

      Organic Letters

      Volume: 18 Issue: 18 Pages: 4488-4490

    • DOI

      10.1021/acs.orglett.6b02203

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 連続した二重連結構造を有するフラバンオリゴマーの合成研究2019

    • Author(s)
      武田梨花子、野口柚華、鈴木啓介、大森 建
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 累積二重連結型フラバンオリゴマーの合成研究2018

    • Author(s)
      武田梨花子、野口柚華、鈴木啓介、大森 建
    • Organizer
      第114回有機合成シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] 高次構造フラボノイドの合成と構造解析2018

    • Author(s)
      大森 建
    • Organizer
      理研シンポジウム「高磁場・高感度NMR利活用のための天然物分野シンポジウム2018」
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Orthogonal Annulation Strategy, Enabling an Efficient Assembly of Doulbly-Linked Oligoflavans2018

    • Author(s)
      Ken Ohmori
    • Organizer
      The 4th International Symposium on Middle Molecular Strategy (ISMMS-4)
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] ポリフェノールの合成から学んだ有機化学2018

    • Author(s)
      大森 建
    • Organizer
      有機合成化学協会関東支部ミニシンポジウム多摩2018
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] 二重連結型フラバンオリゴマーの de novo合成と甘味活性評価2018

    • Author(s)
      大森 建、武田梨花子、野口柚華、三坂 巧、鈴木啓介
    • Organizer
      第60回天然有機化合物討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 美しき天然物を美しき戦略で攻略する2018

    • Author(s)
      大森 建
    • Organizer
      日本化学会化学フェスタ2018
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Synthetic Studies on Flavan-Derived Natural Polyphenols2018

    • Author(s)
      Ken Ohmori
    • Organizer
      ACP-Lectureship Tour in China (at Otsuka Shanghai Research Institute)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Stereochemical-Relay Strategy in Polycycllic Natural Product Syntheses2018

    • Author(s)
      Ken Ohmori
    • Organizer
      ACP-Lectureship Tour in China (at Shanghai Institute of Materia Medica)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] De novo synthetic approach to flavan-derived natural polyphenols2018

    • Author(s)
      Ken Ohmori
    • Organizer
      ACP-Lectureship Tour in China (at Shanghai Institute of Organic Chemistry)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Stereochemical-Relay Strategy in Polycycllic Natural Product Syntheses2018

    • Author(s)
      Ken Ohmori
    • Organizer
      ACP-Lectureship Tour in China (at Shanghai Institute of Organic Chemistry)
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] Total Synthesis of Oxirapentyn D, a Highly Oxidized Chromene Natural Product2018

    • Author(s)
      Takahiro Sakai, Keisuke Suzuki, Ken Ohmori
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 累積二重連結型フラバンオリゴマーの合成研究2018

    • Author(s)
      武田梨花子、瀬古雄介、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] カテキン類の新規効率合成法2018

    • Author(s)
      福井謙一、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] Synthetic Studies on Flavan-Derived Natural Polyphenols2018

    • Author(s)
      Ken Ohmori
    • Organizer
      The 27th Mona Symposium
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 高次構造を有するフラボノイド系ポリフェノールの合成研究と機能開拓2017

    • Author(s)
      大森 建
    • Organizer
      第112回有機合成シンポジウム
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] ベニバナの赤色色素カルタミンの不斉全合成2017

    • Author(s)
      浅見幸平、林大貴、大森建、鈴木啓介
    • Organizer
      第112回有機合成シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] First Total Synthesis of Carthamin: a Traditional Flower Pigment2017

    • Author(s)
      Ken Ohmori
    • Organizer
      The 12th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-12)
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Total Synthesis of (-)-Rotenone and (-)-Deguelin2017

    • Author(s)
      Seiya Matsuoka, Kayo Nakamura, Ken Ohmori, Keisuke Suzuki
    • Organizer
      The 26th International Society of Heterocyclic Chemistry (26th ISHC Congress)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 1,2-転位反応を鍵とするロテノン類の全合成研究2017

    • Author(s)
      松岡 誠也・中村 佳代・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
    • Related Report
      2016 Annual Research Report
  • [Presentation] エスクリタンニンCの全合成研究2017

    • Author(s)
      瀬古 雄介・野口 柚華・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
    • Related Report
      2016 Annual Research Report
  • [Presentation] オルトゴナル法を用いた連続二重連結型フラバンオリゴマーの合成研究2017

    • Author(s)
      野口柚華、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
    • Related Report
      2016 Annual Research Report
  • [Presentation] ベニバナ色素カルタミンの合成研究:対象化/非対称化に基づく立体選択的アプローチ2017

    • Author(s)
      浅見 幸平・林 大貴・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
    • Related Report
      2016 Annual Research Report
  • [Presentation] β位にフルオロ基を有するパラキノンモノアセタールの合成とその反応性2017

    • Author(s)
      阿部 徳子・Reinhardt Katja・松下 享平・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
    • Related Report
      2016 Annual Research Report
  • [Presentation] Aryl Fluorides: a Versatile Synthetic Platform for Natural Product Synthesis2017

    • Author(s)
      Ken Ohmori
    • Organizer
      7th CCS-CSJ Young Chemists Forum 2017
    • Place of Presentation
      慶應義塾大学日吉キャンパス
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 甘味ポリフェノールSelligueainAの合成研究2016

    • Author(s)
      野口柚華、伊藤勇次、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
    • Related Report
      2016 Annual Research Report
  • [Presentation] アリール基の1,2-転位を利用したイソフラボノイド類の合成研究2016

    • Author(s)
      中村佳代、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
    • Related Report
      2016 Annual Research Report

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Published: 2016-04-21   Modified: 2020-03-30  

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