Synthesis of (S)-(-)-N-acetylcolchinol using intramolecular biaryl oxidative coupling

Org Biomol Chem. 2006 Jun 7;4(11):2193-207. doi: 10.1039/b603857c. Epub 2006 May 2.

Abstract

An asymmetric synthesis of the tubulin polymerisation inhibitor (S)-(-)-N-acetylcolchinol is reported based on an intramolecular biaryl oxidative coupling of a 1,3-diarylpropyl acetamide intermediate using phenyliodonium bis(trifluoroacetate) as the final step. Three syntheses of the penultimate 1,3-diarylpropyl acetamide intermediate (S)-(-)-N-[1-[3-(tert-butyldimethylsilyloxy)phenyl)]-3-(3,4,5-trimethoxyphenyl)propyl] acetamide are described which differ in the means by which the stereogenic centre was introduced.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetamides / chemistry
  • Colchicine / analogs & derivatives*
  • Colchicine / chemical synthesis
  • Colchicine / chemistry
  • Crystallography, X-Ray
  • Molecular Structure
  • Onium Compounds / chemistry
  • Oxidation-Reduction
  • Stereoisomerism
  • Tubulin Modulators / chemical synthesis
  • Tubulin Modulators / chemistry

Substances

  • Acetamides
  • Onium Compounds
  • Tubulin Modulators
  • phenyliodonium
  • N-acetylcolchinol
  • Colchicine