A Synthetic Approach to the Stemona Alkaloids

Mira M. Hinman and Clayton H. Heathcock*
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720
J. Org. Chem., 2001, 66 (23), pp 7751–7756
DOI: 10.1021/jo0106391
Publication Date (Web): October 25, 2001
Copyright © 2001 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.

, heathcock@cchem.berkeley.edu

Abstract

Abstract Image

This paper describes our work developing a strategy for the construction of the typical core structure of the Stemona alkaloids. The approach is to control the relative stereochemistry of the groups on the core 1-azabicyclo[5.3.0]decane ring system by a [3,3] sigmatropic rearrangement of an acylimmonium ion followed by selective reduction. After optimization, this reaction sequence afforded the desired diastereomer in 62% yield. Further efforts were directed toward elaboration of the characteristic butyrolactone substituent.

View: Full Text HTML | Hi-Res PDF

Tools

History

  • Published In Issue November 16, 2001
  • Received June 22, 2001

Recommend & Share

Related Content

Other ACS content by these authors: