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Chin. J. Org. Chem. ›› 2007, Vol. 27 ›› Issue (9): 1171-1175. Previous Articles     Next Articles

Reports

苯并螺环β-溴代酮Wagner-Meerwein重排反应研究及其在(±)-Colchicine形式合成中的应用

王爱霞，宋振雷，高栓虎，姜毅君，袁道义，涂永强*, 李宁子   

  1. (兰州大学化学化工学院 功能有机分子化学国家重点实验室 兰州 730000)
  • 收稿日期:2006-12-15 修回日期:2007-02-12 发布日期:2007-08-30
  • 通讯作者: 涂永强

Studies on Wagner-Meerwein Rearrangement of Benzospirocyclic β-Bromo Ketones and Application to Formal Synthesis of (±)-Colchicine

WANG Ai-Xia,SONG Zhen-Lei,GAO Shuan-Hu,JIANG Yi-Jun
YUAN Dao-Yi,TU Yong-Qiang*,LI Ning-Zi   

  1. (State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering,
    Lanzhou University, Lanzhou 730000)
  • Received:2006-12-15 Revised:2007-02-12 Published:2007-08-30
  • Contact: TU Yong-Qiang

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Studies on the Wagner-Meerwein rearrangement of benzospirocyclic β-bromo ketones to n,7,6- tricyclic systems under the promotion of AgBF4 are reported in this paper. Application of this method led to a new approach to 7,7,6-membered core, and thus constituents a formal synthesis of (±)-colchicine.

Key words: (±)-colchicine, benzospirocyclic β-bromo ketones, tricyclic system, Wagner-Meerwein rearrangement, AgBF4