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Synthetic Studies of Dimeric Alkaloids which Control Neuronal Differentiation

Research Project

Project/Area Number 21850003
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeSingle-year Grants
Research Field Chemistry related to living body
Research InstitutionKyoto University

Principal Investigator

TSUKANO Chihiro  Kyoto University, 薬学研究科, 助教 (70524255)

Project Period (FY) 2009 – 2010
Project Status Completed (Fiscal Year 2010)
Budget Amount *help
¥2,704,000 (Direct Cost: ¥2,080,000、Indirect Cost: ¥624,000)
Fiscal Year 2010: ¥1,287,000 (Direct Cost: ¥990,000、Indirect Cost: ¥297,000)
Fiscal Year 2009: ¥1,417,000 (Direct Cost: ¥1,090,000、Indirect Cost: ¥327,000)
Keywords全合成 / アルカロイド / コンプラナジン / リコジン / Diels-Alder反応 / Heck反応 / 生合成
Research Abstract

Complanadines, dimeric alkaloids in the lycodine class alkaloids, induce secretion of neurotrophic factors from 1321N1 cells, which promotes neuronal differentiation of PC-12 cells and enhances expression of mRNA for nerve growing factor (NGF). Because of the unique structure and interesting biological activities, we started synthetic studies for disclose the origin of biological activities. So far, we established a convenient synthetic route to (±)-lycodine by using Diels-Alder and intramolecular Mizoroki-Heck reactions. This strategy will be readily applicable to the total syntheses of related natural products including complanadines and synthetic analogues for structure-activity relationship studies.

Report

(3 results)
  • 2010 Annual Research Report   Final Research Report ( PDF )
  • 2009 Annual Research Report
  • Research Products

    (26 results)

All 2011 2010 2009 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results) Presentation (11 results) Book (2 results) Remarks (3 results)

  • [Journal Article] Control of 6-Exo and 7-Endo Cyclization of Alkynylamides using Platinum and Bismuth Catalysts.2011

    • Author(s)
      Anne-Lise Girard, Taro Enomoto, Shinsuke Yokouchi, Chihiro Tsukano, Yoshiji Takemoto
    • Journal Title

      Chem.Aisan J. 印刷中

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Flexible Strategy for Syntheses of Spirooxindoles using Palladium-catalyzed Carbosilylation and Sakurai-type Cyclization.2011

    • Author(s)
      Sudhir M.Hande, Motoyuki Nakajima, Haruhi Kamisaki, Chihiro Tsukano, Yoshiji Takemoto
    • Journal Title

      Org.Lett.

      Pages: 1828-1831

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Domino Pd-Catalyzed Heck-Type Cyclization and Bi-Catalyzed Hydroamination : Formal Syntheses of Elacomine and Isoelacomine.2011

    • Author(s)
      Haruhi Kamisaki, Tsuyoshi Nanjo, Chihiro Tsukano, Yoshiji Takemoto
    • Journal Title

      Chem.Eur.J. 17

      Pages: 626-633

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Domino Pd-Catalyzed Heck-Type Cyclization and Bi-Catalyzed Hydroamination : Formal Syntheses of Elacomine and Isoelacomine2011

    • Author(s)
      Haruhi Kamisaki, Tsuyoshi Nanjo, Chihiro Tsukano, Yoshiji Takemoto
    • Journal Title

      Chemistry-A European Journal

      Volume: 17 Pages: 626-630

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Flexible Strategy for Syntheses of Spirooxindoles using Palladium-catalyzed Carbosilylation and Sakurai-type Cyclization2011

    • Author(s)
      Sudhir M.Hande, Motoyuki Nakajima, Haruhi Kamisaki, Chihiro Tsukano, Yoshiji Takemoto
    • Journal Title

      Organic Letters

      Volume: 13 Pages: 1828-1831

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Control of 6-Exo and 7-Endo Cyclization of Alkynylamides using Platinum and Bismuth Catalysts2011

    • Author(s)
      Anne-Lise Girard, Taro Enomoto, Shinsuke Yokouchi, Chihiro Tsukano, Yoshiji Takemoto
    • Journal Title

      Chemistry-An Asian Journal

      Volume: 6(掲載確定)

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] "Dionicio R.Siegel and Samuel J.Danishefsky"多環状多プレニルアシルフロログルシノール類の全合成2010

    • Author(s)
      塚野千尋
    • Journal Title

      有機合成化学協会誌 68

      Pages: 592-600

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Concise Total Synthesis of (±)-Lycodine.2010

    • Author(s)
      Chihiro Tsukano, Le Zhao, Yoshiji Takemoto, Masahiro Hirama
    • Journal Title

      Eur.J.Org.Chem.

      Pages: 4198-4200

    • Related Report
      2010 Final Research Report
    • Peer Reviewed
  • [Journal Article] Concise Total Synthesis of (±)-Lycodine2010

    • Author(s)
      Chihiro Tsukano, Le Zhao, Yoshiji Takemoto, Masahiro Hirama
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2010 Pages: 4198-4200

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 多環状多プレニルアシルフロログルシノール類の全合成2010

    • Author(s)
      塚野千尋、D.R.Siegel, S.J.Danishefsky
    • Journal Title

      有機合成化学協会誌

      Volume: 68 Pages: 592-600

    • NAID

      10026869311

    • Related Report
      2010 Annual Research Report
    • Peer Reviewed
  • [Presentation] リコジンのラセミ全合成2010

    • Author(s)
      塚野千尋
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      大阪 (近畿大学)
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] Pd触媒によるシリルアミド化反応を鍵反応としたスピロオキシインドール骨格合成法の開発2010

    • Author(s)
      塚野千尋
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山 (岡山大学)
    • Year and Date
      2010-03-28
    • Related Report
      2009 Annual Research Report
  • [Presentation] Total synthesis of racemic lycodine2010

    • Author(s)
      塚野千尋, 趙楽, 竹本佳司, 平間正博
    • Organizer
      PACIFICHEM2010
    • Place of Presentation
      Honolulu, Hawaii
    • Related Report
      2010 Annual Research Report 2010 Final Research Report
  • [Presentation] パラジウム触媒によるシリルアミド化を鍵反応としたスピロオキシインドール骨格合成法の開発2010

    • Author(s)
      塚野千尋、Sudhir M.Hande、上崎春陽、中島基之、竹本佳司
    • Organizer
      第40回複素環化学討論会
    • Place of Presentation
      仙台
    • Related Report
      2010 Final Research Report
  • [Presentation] 多環性生理活性天然物の全合成研究2010

    • Author(s)
      塚野千尋
    • Organizer
      第45回天然物化学談話会
    • Place of Presentation
      愛知・蒲郡
    • Related Report
      2010 Final Research Report
  • [Presentation] リコジンのラセミ全合成2010

    • Author(s)
      塚野千尋、趙楽、竹本佳司、平間正博
    • Organizer
      第8回次世代を担う有機化学シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2010 Final Research Report
  • [Presentation] Pd触媒によるシリルアミド化反応を鍵反応としたスピロオキシインドール骨格合成法の開発2010

    • Author(s)
      Sudhir M.Hande,上崎春陽,塚野千尋,竹本佳司
    • Organizer
      日本薬学会第130年会
    • Place of Presentation
      岡山
    • Related Report
      2010 Final Research Report
  • [Presentation] リコジンのラセミ全合成2010

    • Author(s)
      塚野千尋、趙楽、竹本佳司、平間正博
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      大阪
    • Related Report
      2010 Final Research Report
  • [Presentation] リコジンのラセミ全合成2010

    • Author(s)
      塚野千尋、趙楽、竹本佳司、平間正博
    • Organizer
      第8回次世代を担う有機化学シンポジウム
    • Place of Presentation
      長井記念ホール(東京)
    • Related Report
      2010 Annual Research Report
  • [Presentation] 多環性生理活性天然物の全合成研究2010

    • Author(s)
      塚野千尋
    • Organizer
      第45回天然物化学談話会
    • Place of Presentation
      三谷温泉ホテル明山荘(愛知・蒲郡)
    • Related Report
      2010 Annual Research Report
  • [Presentation] パラジウム触媒によるシリルアミド化を鍵反応としたスピロオキシインドール骨格合成法の開発2010

    • Author(s)
      塚野千尋・Sudhir M.Hande・上崎春陽・中島基之・竹本佳司
    • Organizer
      第40回複素環化学討論会
    • Place of Presentation
      仙台市民会館(仙台)
    • Related Report
      2010 Annual Research Report
  • [Book] 巨大ポリエーテル天然物・ギムノシン-Aの全合成(天然物全合成の最新動向)2009

    • Author(s)
      佐々木誠、塚野千尋
    • Publisher
      シーエムシー出版
    • Related Report
      2010 Final Research Report
  • [Book] 天然物全合成の最新動向 第15章 巨大ポリエーテル天然物・ギムノシンーAの全合成2009

    • Author(s)
      佐々木誠・塚野千尋
    • Total Pages
      16
    • Publisher
      シーエムシー出版
    • Related Report
      2009 Annual Research Report
  • [Remarks] ホームページ等

    • URL

      http://www.pharm.kyoto-u.ac.jp/orgchem/

    • Related Report
      2010 Final Research Report
  • [Remarks]

    • URL

      http://www.pharm.kyoto-u.ac.jp/orgchem/04_ron.html

    • Related Report
      2010 Annual Research Report
  • [Remarks]

    • URL

      http://www.pharm.kyoto-u.ac.jp/orgchem/05_gak.html

    • Related Report
      2010 Annual Research Report

URL: 

Published: 2009-04-01   Modified: 2016-04-21  

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