Total synthesis of hypermodified epothilone analogs with potent in vitro antitumor activity

Org Lett. 2008 Mar 20;10(6):1183-6. doi: 10.1021/ol800089x. Epub 2008 Feb 28.

Abstract

The convergent total synthesis of hypermodified epothilone analogs 1 and 2 has been achieved with the stereoselective cyclopropanation of allylic alcohol 17 and ring-closing olefin metathesis with diene 22 as the key steps. In spite of significant structural differences between these analogs and the natural epothilone scaffold, 1 and 2 are potent inducers of tubulin polymerization and inhibit the growth of human cancer cells in vitro with sub-nM IC50 values.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Cell Line, Tumor
  • Chromatography, High Pressure Liquid
  • Drug Screening Assays, Antitumor
  • Epothilones / chemical synthesis*
  • Epothilones / chemistry
  • Humans
  • In Vitro Techniques
  • Magnetic Resonance Spectroscopy
  • Molecular Structure

Substances

  • Antineoplastic Agents
  • Epothilones