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Synthetic study of ellagitannins based on coupling reactions between two aromatic rings

Research Project

Project/Area Number 15K07854
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionUniversity of Toyama

Principal Investigator

Abe Hitoshi  富山大学, 大学院理工学研究部(工学), 教授 (70221728)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,040,000 (Direct Cost: ¥800,000、Indirect Cost: ¥240,000)
Fiscal Year 2016: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2015: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords全合成 / 芳香族化合物 / カップリング反応 / グルコース / ポリフェノール / Ullmann 反応 / 軸不斉 / 没食子酸 / 酸化的フェノールカップリング / エラジタンニン / Ullmann反応
Outline of Final Research Achievements

Although ellagitannins, which are natural polyphenol compounds, composed of only limited structures, glucose and gallic acid, many kinds of compounds have been known. Since ellagitannin compounds often exhibit interesting biological activities, they have been expected to be medicinal seeds. However, studies on organic synthesis of ellagitannins have insufficiently progressed, and a few examples of total synthesis of simple ellagitannins have been reported. In this study, we challenged syntheses of complex-structured ellagitannins based on coupling reactions between two gallic acids, involving the C-C or C-O oxidative coupling.

Report

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

    (23 results)

All 2018 2017 2016 2015

All Journal Article (5 results) (of which Peer Reviewed: 5 results,  Acknowledgement Compliant: 3 results) Presentation (18 results) (of which Int'l Joint Research: 1 results,  Invited: 1 results)

  • [Journal Article] Improved Synthesis of Nigricanin2017

    • Author(s)
      H. Abe, T. Nagai, H. Imai, Y. Horino
    • Journal Title

      Chem. Pharm. Bull.

      Volume: 65 Pages: 1078-1080

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Natural Product Syntheses Using Biaryl Coupling Reactions2017

    • Author(s)
      阿部 仁
    • Journal Title

      Journal of Synthetic Organic Chemistry, Japan

      Volume: 75 Issue: 8 Pages: 850-863

    • DOI

      10.5059/yukigoseikyokaishi.75.850

    • NAID

      130005966766

    • ISSN
      0037-9980, 1883-6526
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Synthesis of Oenothein C2017

    • Author(s)
      H. Abe, D. Ogura, Y. Horino
    • Journal Title

      Heterocycles

      Volume: 95 Issue: 1 Pages: 131-136

    • DOI

      10.3987/com-16-s(s)6

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Initial Synthesis of Valoneic and Woodfordinic Acid Dilactones2016

    • Author(s)
      H. Abe, S. Ishikura, Y. Horino
    • Journal Title

      Synlett

      Volume: 27 Issue: 06 Pages: 859-863

    • DOI

      10.1055/s-0035-1561271

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 2,3,9,10-Tetraoxygenated Benzo[c]phenanthridine Derivatives via Palladium-mediated Aryl-aryl Coupling Reaction2016

    • Author(s)
      H. Abe, N. Kobayashi, Y. Kadoshima, Y. Takeuchi, T. Harayama, Y. Horino
    • Journal Title

      Heterocycles

      Volume: 91 Issue: 2 Pages: 673-673

    • DOI

      10.3987/com-15-s(t)56

    • NAID

      120006799047

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] isoDHDG unit 及び Nilotinin M3 の合成研究2018

    • Author(s)
      今井遥、堀野良和、阿部仁
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Ullorithin 類の網羅的合成に向けた Urolithin A glucuronide の位置選択的合成研究2018

    • Author(s)
      永井孝典、西森豪、堀野良和、阿部仁
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Isorugosin B の合成研究2018

    • Author(s)
      江本萌、梅基大地、堀野良和、阿部仁
    • Organizer
      日本薬学会第138年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Ullmann反応を鍵とするエラジタンニン類の合成研究2017

    • Author(s)
      小倉大知、加藤由泰、今井遥、堀野良和、阿部仁
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] Isoschimawalin A の合成研究2017

    • Author(s)
      平岡翔太郎、小倉大知、石倉慎吾、堀野良和、阿部仁
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] Nigricanin の改良合成2017

    • Author(s)
      永井孝典、今井遥、堀野良和、阿部仁
    • Organizer
      日本薬学会第137年会
    • Place of Presentation
      仙台
    • Year and Date
      2017-03-24
    • Related Report
      2016 Research-status Report
  • [Presentation] Isoschimawalin A の全合成研究2017

    • Author(s)
      平岡翔太郎、小倉大知、石倉慎吾、堀野良和、阿部仁
    • Organizer
      第43回反応と合成の進歩シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 銅を用いたジアリールエーテルの構築及びエラジタンニン類の合成研究2017

    • Author(s)
      今井遥、小倉大知、加藤由泰、堀野良和、阿部仁
    • Organizer
      第47回複素環化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Urolithin A Glucuronide の位置選択的合成研究2017

    • Author(s)
      永井孝典、西森豪、堀野良和、阿部仁
    • Organizer
      平成29年度有機合成化学北陸セミナー
    • Related Report
      2017 Annual Research Report
  • [Presentation] isoDHDG unit の合成研究2016

    • Author(s)
      今井遥、堀野良和、阿部仁
    • Organizer
      有機合成化学北陸セミナー
    • Place of Presentation
      金沢
    • Year and Date
      2016-10-07
    • Related Report
      2016 Research-status Report
  • [Presentation] ニグリカニンの合成2016

    • Author(s)
      永井孝典、今井遥、堀野良和、阿部仁
    • Organizer
      有機合成化学北陸セミナー
    • Place of Presentation
      金沢
    • Year and Date
      2016-10-07
    • Related Report
      2016 Research-status Report
  • [Presentation] Synthesis of Biaryl-type Natural Products2016

    • Author(s)
      Hitoshi Abe
    • Organizer
      The First International Symposium on Toyama-Asia-Africa Pharmaceutical Network
    • Place of Presentation
      富山
    • Year and Date
      2016-09-12
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research / Invited
  • [Presentation] Ullmann 反応を利用するエラジタンニン類の合成2016

    • Author(s)
      加藤由泰、小倉大知、石倉慎吾、堀野良和、阿部仁
    • Organizer
      日本プロセス化学会2016サマーシンポジウム
    • Place of Presentation
      名古屋
    • Year and Date
      2016-07-28
    • Related Report
      2016 Research-status Report
  • [Presentation] エラジタンニンの合成研究:DHDG 及び isoDHDG ユニットの合成2016

    • Author(s)
      今井遥、塩江一磨、堀野良和、阿部仁
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-27
    • Related Report
      2015 Research-status Report
  • [Presentation] Coriariin B の合成研究2016

    • Author(s)
      加藤由泰、石倉慎吾、塩江一磨、堀野良和、阿部仁
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      京田辺
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] IsoschimawalinA の全合成研究2016

    • Author(s)
      平岡翔太郎、小倉大知、石倉慎吾、堀野良和、阿部仁
    • Organizer
      日本化学会近畿支部北陸地区講演会と研究発表会
    • Place of Presentation
      福井
    • Related Report
      2016 Research-status Report
  • [Presentation] エラジタンニンの合成研究:isoDHDG ユニットの合成2016

    • Author(s)
      今井遥、堀野良和、阿部仁
    • Organizer
      第36回有機合成若手セミナー
    • Place of Presentation
      京都
    • Related Report
      2016 Research-status Report
  • [Presentation] 古典的 Ullmann 反応を応用した coriariin B の全合成研究2015

    • Author(s)
      加藤由泰、石倉慎吾、塩江一磨、堀野良和、阿部仁
    • Organizer
      有機合成化学北陸セミナー
    • Place of Presentation
      富山
    • Year and Date
      2015-10-02
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2019-03-29  

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