Total synthesis of chivosazole F

J Am Chem Soc. 2010 Oct 6;132(39):13610-1. doi: 10.1021/ja107290s.

Abstract

The first synthesis of the highly biologically active chivosazole F is described. It features an intramolecular Stille coupling for the macrolactone formation and thereby circumvents the problem of isomerization associated with the tetraene segment. Additionally, the synthesis confirms the structure which has been proposed based solely on a combination of NMR/computational methods and genetic analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Macrolides / chemical synthesis*
  • Macrolides / chemistry
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Macrolides
  • chivosazole F