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Keywords:

  • cycloaddition;
  • cyclopentadienone;
  • microtubule inhibitor;
  • natural product;
  • total synthesis

Abstract

Thumbnail image of graphical 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.