Enantioselective total synthesis of (-)-zampanolide, a potent microtubule-stabilizing agent

Org Lett. 2011 Aug 5;13(15):4108-11. doi: 10.1021/ol201626h. Epub 2011 Jul 12.

Abstract

An enantioselective total synthesis of zampanolide has been accomplished using a novel DDQ/Brønsted acid promoted cyclization as the key reaction. The synthesis features cross-metathesis to construct the trisubstituted olefin and a ring-closing metathesis to form the macrolactone. The final N-acyl aminal formation was stereoselectively accomplished by an organocatalytic reaction.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Cyclization
  • Excipients / chemical synthesis*
  • Macrolides / chemical synthesis*
  • Microtubules / metabolism
  • Molecular Structure
  • Stereoisomerism

Substances

  • Excipients
  • Macrolides
  • zampanolide