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

Organic & Biomolecular Chemistry Pub Date: 2006-05-02 DOI: 10.1039/B603857C

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.

Graphical abstract: Synthesis of (S)-(?)-N-acetylcolchinol using intramolecular biaryl oxidative coupling
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