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Development of one-pot synthesis of 3a-subsituted pyrroloindole and exhaustive synthesis of associated biologically active natural products

Research Project

Project/Area Number 25860014
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionMeiji Pharmaceutical University

Principal Investigator

Tayu Masanori  明治薬科大学, 薬学部, 助手 (20632780)

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 2015: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2013: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsインドール / 天然物合成 / 不斉合成 / C2対称性 / スルホキシド / アルカロイド / 有機化学 / 天然物 / 複素環 / ピロロインドール / ワンポット / ヘテロカップリング
Outline of Final Research Achievements

DMSO/Tf2O Mediated one-pot construction of 3a-substituted pyrroloindole framework has been developed. In investigation of a variety of nucleophiles, the synthetic method of 3-(1-indolyl)pyrroloindole framework with indoline nucleus has been developed, which was applied in total synthesis of (±)-psychotriasine.
In the case of tryptamine nucleophile, one-pot synthesis of bisquaternary carbon containing bispyrroloindole core has been achieved. Furthermore, the first one-pot heterodimerization has been successfully developed with tryptamine derivative which was different from starting one.
In addition, enantioselective synthetic method has been achieved with newly designed C2-symmetric chiral sulfoxide. The synthetic utility of this method was declared through the enantioselective total synthesis of (+)-psychotriasine.

Report

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

    (11 results)

All 2016 2015 2014 Other

All Journal Article (4 results) (of which Peer Reviewed: 4 results,  Acknowledgement Compliant: 1 results) Presentation (7 results) (of which Int'l Joint Research: 1 results)

  • [Journal Article] C2-Symmetric Chiral Sulfoxide-Mediated Intermolecular Interrupted Pummerer Reaction for Enantioselective Construction of C3a-Substituted Pyrroloindolines2016

    • Author(s)
      Masanori Tayu, Takako Ishizaki, Kazuhiro Higuchi, Tomomi Kawasaki
    • Journal Title

      Synlett

      Volume: 27 Issue: 06 Pages: 941-945

    • DOI

      10.1055/s-0035-1560548

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] DMSO/Tf2O-Mediated Cross-Coupling of Tryptamine with Substituted Aniline to Access C3a-N1'-Linked Pyrroloindoline Alkaloids2015

    • Author(s)
      M. Tayu, T. Ishizaki, K. Higuchi, T. Kawasaki
    • Journal Title

      Org. Biomol. Chem.

      Volume: 13 Issue: 13 Pages: 3863-3865

    • DOI

      10.1039/c5ob00190k

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Asymmetric Total Synthesis of (–)-Leuconoxine via Chiral Phosphoric Acid-Catalyzed Desymmetrization of a Prochiral Diester2015

    • Author(s)
      K. Higuchi, S. Suzuki, R. Ueda, N. Oshima, E. Kobayashi, M. Tayu, T. Kawasaki
    • Journal Title

      Org. Lett.

      Volume: 17 Issue: 1 Pages: 154-157

    • DOI

      10.1021/ol5033865

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Hypervalent Iodine Mediated One-pot C-H Functionarization at 2α- or 3α-Position of Indole Derivatives2014

    • Author(s)
      K. Higuchi, M. Inaba, A. Naganuma, T. Ishizaki, M. Tayu, T. Kawasaki
    • Journal Title

      Heterocycles

      Volume: 89 Issue: 9 Pages: 2105-2121

    • DOI

      10.3987/com-14-13065

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Presentation] C2対称キラルスルホキシドにより誘起されるエナンチオ選択的分子間Interrupted Pummerer 反応2015

    • Author(s)
      田湯正法、鈴木由衣、樋口和宏、川﨑知己
    • Organizer
      第45回複素環化学討論会
    • Place of Presentation
      東京
    • Year and Date
      2015-11-20
    • Related Report
      2015 Annual Research Report
  • [Presentation] Chiral Sulfoxide-Mediated First Intermolecular Interrrupted Pummerer Reaction for Enantioselective Synthesis of C3a-Substituted Pyrroloindolines2015

    • Author(s)
      Tayu M, Suzuki Y, Higuchi K, Kawasaki T
    • Organizer
      13th International Kyoto Conference New Aspects of Organic Chemistry
    • Place of Presentation
      京都
    • Year and Date
      2015-11-11
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] DMSO-TFAAによるインドール2位での芳香族求核置換反応の開発2015

    • Author(s)
      河内 晃樹, 田湯 正法, 樋口 和宏, 川﨑 知己
    • Organizer
      日本薬学会 第135年会
    • Place of Presentation
      デザイン・クリエイティブセンター神戸
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Research-status Report
  • [Presentation] キラルスルホキシドを用いた 3a-インドリルピロロインドリン骨格のワンポット不斉合成法の開発2014

    • Author(s)
      田湯正法, 樋口和宏, 鈴木由衣, 川﨑知己
    • Organizer
      第40回反応と合成の進歩シンポジウム
    • Place of Presentation
      東北大学 川内萩ホール
    • Year and Date
      2014-11-10 – 2014-11-11
    • Related Report
      2014 Research-status Report
  • [Presentation] 天然物合成を指向した3a 位置換ピロロインドリン骨格のワンポット構築反応

    • Author(s)
      田湯正法
    • Organizer
      第11回次世代を担う有機化学シンポジウム
    • Place of Presentation
      日本薬学会長井記念ホール
    • Related Report
      2013 Research-status Report
  • [Presentation] 高効率的3a 位置換ピロロインドリン骨格構築法の開発と天然物合成への応用

    • Author(s)
      田湯正法
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      九州大学医学部 百年講堂
    • Related Report
      2013 Research-status Report
  • [Presentation] 3a位置換ピロロインドリンのone-pot合成法

    • Author(s)
      石﨑貴子
    • Organizer
      日本薬学会第134年会
    • Place of Presentation
      熊本市総合体育館
    • Related Report
      2013 Research-status Report

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

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