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Issue 11, 2006
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Synthesis of (S)-(−)-N-acetylcolchinol using intramolecular biaryl oxidative coupling

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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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Publication details

The article was received on 15 Mar 2006, accepted on 31 Mar 2006 and first published on 02 May 2006


Article type: Paper
DOI: 10.1039/B603857C
Citation: Org. Biomol. Chem., 2006,4, 2193-2207
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    Synthesis of (S)-(−)-N-acetylcolchinol using intramolecular biaryl oxidative coupling

    G. Besong, K. Jarowicki, P. J. Kocienski, E. Sliwinski and F. T. Boyle, Org. Biomol. Chem., 2006, 4, 2193
    DOI: 10.1039/B603857C

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