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Stereoselective synthesis of dimeric indole alkaloids utilizing effective construction reaction of quaternary carbon center

Research Project

Project/Area Number 24590032
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionMeiji Pharmaceutical University

Principal Investigator

KAWASAKI TOMOMI  明治薬科大学, 薬学部, 名誉教授 (70161304)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2013: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2012: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsインドールアルカロイド / 第四級炭素 / ドミノ反応 / 立体選択的反応 / 構造活性相関 / 有機化学 / 合成化学 / 薬学
Outline of Final Research Achievements

The synthesis of 2-indolinones including adjacent quaternary carbon centers was performed by the diastereoselective cascade reaction (olefination-isomerization-Claisen rearrangement) of 2-allyloxy-3-indolinones. The scope and limitation of the cascade reaction were defined. By applying this reaction, the construction of backbone architecture having all carbons of natural product communesin F was achieved. The syntheses of phenserine and 5-N-acetylardeemin derivatives and evaluations of their acetyl-/butyryl-cholinesterase and ABCG2-transporter inhibitory were performed to show their structure–activity relationship study (SARS), respectively. The synthetic route to the related compound isoroquefortine was confirmed for its SARS.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (20 results)

All 2015 2014 2013 2012

All Journal Article (7 results) (of which Peer Reviewed: 7 results,  Acknowledgement Compliant: 1 results) Presentation (13 results)

  • [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 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and ABCG2 inhibitory evaluation of 5-N-acetylardeemin derivatives2015

    • Author(s)
      D. Hayashi, N. Tsukioka, Y. Inoue, Y. Matsubayashi, T. Iizuka, K. Higuchi, Y. Ikegami, T. Kawasaki
    • Journal Title

      Bioorg. Med. Chem.

      Volume: 23 Issue: 9 Pages: 2010-2023

    • DOI

      10.1016/j.bmc.2015.03.017

    • Related Report
      2014 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 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Thionium-Based One-Pot Construction of Homo-/Heterodimeric Pyrroloindoline from Tryptamine2014

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

      Org. Lett.

      Volume: 16 Issue: 14 Pages: 3613-3615

    • DOI

      10.1021/ol5012373

    • Related Report
      2014 Annual Research 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 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Sulfoxide-TFAA and Nucleophile Combination as New Reagent for Aliphatic C-H Functionalization at Indole 2α-position2013

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

      Org. Biomol. Chem.

      Volume: 11 Issue: 3 Pages: 496-502

    • DOI

      10.1039/c2ob26944a

    • Related Report
      2013 Research-status Report 2012 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthesis of phenserine analogues and evaluation of their cholinesterase inhibitory activities.2012

    • Author(s)
      M. Shinada, F. Narumi, Y. Osada, K. Matsumoto, T. Yoshida, K. Higuchi, T. Kawasaki, H. Tanaka and M. Satoh
    • Journal Title

      Bioorganic & Medicinal Chem.

      Volume: 20 Issue: 16 Pages: 4901-4914

    • DOI

      10.1016/j.bmc.2012.06.048

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] 血小板凝集阻害剤を目指した非ペプチド性RGDミミックに関する研究2015

    • Author(s)
      村山明日美、疋田英樹、加藤愛理、樋口和宏、川崎知己
    • Organizer
      日本薬学会 第135年会
    • Place of Presentation
      神戸
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Annual Research Report
  • [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、川崎知己
    • Organizer
      日本薬学会 第135年会
    • Place of Presentation
      神戸
    • Year and Date
      2015-03-25 – 2015-03-28
    • Related Report
      2014 Annual Research Report
  • [Presentation] 血小板凝集阻害剤を目指した非ペプチド性 RGDミックの合成2014

    • Author(s)
      村山明日美、疋田英樹、加藤愛理、樋口和宏、川崎知己
    • Organizer
      第68 回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟
    • Year and Date
      2014-11-29 – 2014-11-30
    • Related Report
      2014 Annual Research Report
  • [Presentation] Roquefortine Cと関連化合物の成研究2014

    • Author(s)
      今西江里、樋口和宏、川崎知己
    • Organizer
      第68 回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟
    • Year and Date
      2014-11-29 – 2014-11-30
    • Related Report
      2014 Annual Research 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
      仙台
    • Year and Date
      2014-11-10 – 2014-11-11
    • Related Report
      2014 Annual Research Report
  • [Presentation] インドール 2α位と3α位への効率的な置換基導入法開発2014

    • Author(s)
      樋口和宏、田湯正法、稲葉真里、長沼明日香、石﨑貴子、川崎知己
    • Organizer
      第52 回日本薬学会 関東支部大会
    • Place of Presentation
      町田
    • Year and Date
      2014-10-04
    • Related Report
      2014 Annual Research Report
  • [Presentation] キラルブレンステッド酸触媒を用いたLeuconoxine の不斉全合成研究2014

    • Author(s)
      大島稚史、上田玲瑛子、鈴木真、小林恵美子、樋口和宏、川崎知己
    • Organizer
      第44 回複素環化学討論会
    • Place of Presentation
      札幌
    • Year and Date
      2014-09-10 – 2014-09-12
    • Related Report
      2014 Annual Research 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2013

    • Author(s)
      田湯正法,樋口和宏,石﨑貴子,川﨑知己
    • Organizer
      第11回次世代を担う有機化学シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2013 Research-status Report
  • [Presentation] 環縮合系2連続第四級炭素の立体選択的構築反応とインドールアルカロイド合成への適用2013

    • Author(s)
      山本由実子、川原塚悠、樋口和宏、川﨑知己
    • Organizer
      第43回複素環化学討論会
    • Place of Presentation
      岐阜
    • Related Report
      2013 Research-status Report
  • [Presentation] 天然物5-N-Acetylardeeminの誘導体合成とABCG2阻害活性評価2013

    • Author(s)
      林大悟、月岡直樹、松林喜樹、井上裕貴、樋口和宏、池上洋二、川﨑知己
    • Organizer
      第31回メディシナルケミストリーシンポジウム
    • Place of Presentation
      広島
    • Related Report
      2013 Research-status Report
  • [Presentation] インドールアルカロイドの合成に向けた立体選択的2連続第四級炭素構築反応2013

    • Author(s)
      山本由実子、田湯正法、樋口和宏、川﨑知己
    • Organizer
      第133薬学会年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Research-status Report
  • [Presentation] Novofumigatamideの合成研究2012

    • Author(s)
      大友陽介、 樋口和宏、川﨑知己
    • Organizer
      第42回複素環化学討論会、2012/10/11-13、
    • Place of Presentation
      京都
    • Related Report
      2012 Research-status Report
  • [Presentation] 5-N-Acetylardeeminの構造活性相関研究2012

    • Author(s)
      林大悟、月岡直樹、樋口和宏、井上裕貴、池上洋二、川﨑知己
    • Organizer
      第64回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟
    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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