Synthesis and stereochemical assignment of (+)-chamuvarinin

Org Lett. 2011 Feb 4;13(3):514-7. doi: 10.1021/ol1028699. Epub 2010 Dec 21.

Abstract

A stereocontrolled total synthesis of (+)-chamuvarinin, isolated from the root extract of Uvaria Chamae, utilizes a convergent modular strategy to construct the adjacently linked C15-C28 ether array, followed by a late-stage Julia-Kocienski olefination to append the butenolide motif. This constitutes the first total synthesis of (+)-chamuvarinin, defining the relative and absolute configuration of this unique annonaceous acetogenin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetogenins / chemical synthesis*
  • Acetogenins / chemistry
  • Molecular Structure
  • Plant Roots / chemistry
  • Stereoisomerism
  • Uvaria / chemistry

Substances

  • Acetogenins
  • chamuvarinin