Enantioselective synthesis of (+)-chamaecypanone C: a novel microtubule inhibitor

Angew Chem Int Ed Engl. 2009;48(8):1494-7. doi: 10.1002/anie.200805486.

Abstract

A bicycle built for tubulin: The total synthesis of (+)-chamaecypanone C has been achieved by using a tandem retro-Diels-Alder/Diels-Alder cascade reaction (see scheme). Initial biological studies demonstrate that (+)-chamaecypanone C is an inhibitor of tubulin assembly and binds at the colchicine site.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bridged Bicyclo Compounds / chemical synthesis*
  • Bridged Bicyclo Compounds / chemistry
  • Bridged Bicyclo Compounds / pharmacology
  • Cell Line, Tumor
  • Humans
  • Inhibitory Concentration 50
  • Potoroidae
  • Rats
  • Stereoisomerism
  • Tubulin Modulators / chemical synthesis*
  • Tubulin Modulators / chemistry
  • Tubulin Modulators / pharmacology

Substances

  • Bridged Bicyclo Compounds
  • Tubulin Modulators
  • chamaecypanone C