Total Synthesis of (±)-Communesin F

Jun Yang, Haoxing Wu, Liqun Shen, and Yong Qin*
Department of Chemistry of Medicinal Natural Products and Key Laboratory of Drug Targeting, West China School of Pharmacy, and State Key Laboratory of Biotherapy, Sichuan University, Chengdu 610041, P. R. China
J. Am. Chem. Soc., 2007, 129 (45), pp 13794–13795
DOI: 10.1021/ja075705g
Publication Date (Web): October 23, 2007
Copyright © 2007 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, yongqin@scu.edu.cn

Abstract

Abstract Image

Total synthesis of the complex polycyclic indole alkaloid (±)-communesin F has been accomplished in 23 reaction steps in about 3% overall yield. The key steps relied on a highly efficient methodology for assembling the pentacyclic substructure 2 with the C7 quaternary carbon, the stereoselective preparation of the second C8 quaternary carbon by a two-step one-pot O-allylation and consecutive 3,3-rearrangement (2 to 3), and the stereoselective acid-catalyzed cyclization of 4 to form the azepine ring (5). These highly stereoselective reactions guaranteed the stereochemical results, allowing the construction of the C, E, F, and G ring systems.

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History

  • Published In Issue November 14, 2007
  • Received July 31, 2007

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