Development of Au-catalyzed tandem cyclization reaction and its application to syntheses of biologically active alkaloids.

• Project/Area Number: 21790004
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Chemical pharmacy
• Research Institution: Tohoku University
• Principal Investigator: SUGIMOTO Kenji Tohoku University, 大学院・薬学研究科, 助教 (60400264)
• Project Period (FY): 2009 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000); Fiscal Year 2010: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2009: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
• Keywords: 金触媒 / 連続環化反応 / アルカロイド合成 / インドリジジン / キノリジジン / ラジニラム / 多置換ピロール / ピロール

Research Abstract

Au-catalyzed tandem cyclizations of ynamide having acetal moiety were established to afford indolizidine and quinolizidine skeletons in one-pot. This strategy was applied to a short and efficient synthesis of anti-tumor alkaloid (-)-rhazinilam. Furthermore, intermolecular version of this reaction was proved to be a convenient method to construct substituted pyrroles.

Research Products

• [Presentation] (2011)
  • Author(s): 豊島和貴、杉本健士、徳山英利
  • Organizer: 日本薬学会第131年会
  • Place of Presentation: 静岡県静岡市
  • Year and Date: 2011-03-30
• [Presentation] (2010)
  • Author(s): 豊島和貴、杉本健士、徳山英利
  • Organizer: 創薬懇話会2010 in蔵王
  • Place of Presentation: 宮城県蔵王町
  • Year and Date: 2010-11-12
• [Presentation] (2010)
  • Author(s): 野中汐里、小滝健太、杉本健士、徳山英利
  • Organizer: 創薬懇話会2010 in蔵王
  • Place of Presentation: 宮城県蔵王町
  • Year and Date: 2010-11-12
• [Presentation] (2010)
  • Author(s): 徳山英利、野中汐里、豊島和貴、小滝健太、杉本健士
  • Organizer: 第36回反応と合成の進歩シンポジウム
  • Place of Presentation: 愛知県名古屋市
  • Year and Date: 2010-11-02
• [Presentation] (2010)
  • Author(s): 野中汐里、小滝健太、杉本健士、徳山英利
  • Organizer: 第49回日本薬学会東北支部大会
  • Place of Presentation: 福島県郡山市
  • Year and Date: 2010-10-24
• [Presentation] (2010)
  • Author(s): 豊島和貴、杉本健士、徳山英利
  • Organizer: 第49回日本薬学会東北支部大会
  • Place of Presentation: 福島県郡山市
  • Year and Date: 2010-10-24
• [Remarks] ホームページ等
  • URL: http://www.pharm.tohoku.ac.jp/~seizou/presentation_2010.html
• [Remarks]
  • URL: http://www.pharm.tohoku.ac.jp/~seizou/presentation_2010.html