Total Synthesis of (±)-Cylindricines A and B

Julie Fields Liu and Clayton H. Heathcock*
Department of Chemistry, University of California, Berkeley, California, 94720
J. Org. Chem., 1999, 64 (22), pp 8263–8266
DOI: 10.1021/jo991020q
Publication Date (Web): October 14, 1999
Copyright © 1999 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.

Abstract

Abstract Image

Cylindricine A (1) and cylindricine B (2) have been synthesized in 11 steps and 19% overall yield. The key reaction involves the addition of an organocopper species to a bicyclic vinylogous amide, which provides complete stereocontrol over the installation of the hexyl side chain.

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History

  • Published In Issue October 29, 1999
  • Received June 25, 1999

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