A convergent approach to (-)-callystatin A based on local symmetry

Chemistry. 2012 Nov 5;18(45):14267-71. doi: 10.1002/chem.201202701. Epub 2012 Sep 27.

Abstract

The key is symmetry! A convergent synthetic approach of the highly cytotoxic natural product (-)-callystatin A was developed assembling three fragments through Julia-Kocienski olefination and Stille cross-coupling. The new strategy relies on a pivotal local symmetry of the target molecule. In this preliminary study, particular attention was devoted to facilitate the catalytic enantiocontrol of strategic stereogenic centers present in each of the fragments (see scheme).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemistry
  • Animals
  • Callyspongia / chemistry
  • Fatty Acids, Unsaturated / chemical synthesis
  • Fatty Acids, Unsaturated / chemistry*
  • Stereoisomerism

Substances

  • Alkenes
  • Fatty Acids, Unsaturated
  • callystatin A