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Novel syntheses of cis and trans isomers of combretastatin A-4

Gaukroger, K, Hadfield, JA, Hepworth, LA, Lawrence, NJ and McGown, AT 2001, 'Novel syntheses of cis and trans isomers of combretastatin A-4' , Journal of Organic Chemistry, 66 (24) , pp. 8135-8138.

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Abstract

A high-yielding, two-step stereoselective synthesis of the anticancer drug (Z)-combretastatin A-4 (1) has been devised. The method uses the Perkin condensation of 3,4,5-trimethoxyphenylacetic acid and 3-hydroxy-4-methoxybenzaldehyde followed by decarboxylation of the cinnamic acid intermediate using copper and quinoline. The iodine-catalyzed isomerization of the Z isomer 1 results in complete conversion to the E isomer. The Suzuki cross-coupling of an aryl boronic acid and vinyl bromide has also been successfully employed to produce both Z and E isomers of combretastatin A-4 stereoselectively. Both methods are far superior to the current five-step Wittig synthesis in which both isomers are produced nonstereoselectively.

Item Type: Article
Themes: Subjects / Themes > Q Science > Q Science (General)
Subjects / Themes > Q Science > QD Chemistry
Subjects outside of the University Themes
Schools: Colleges and Schools > College of Science & Technology
Colleges and Schools > College of Science & Technology > School of Environment and Life Sciences
Colleges and Schools > College of Science & Technology > School of Environment and Life Sciences > Biomedical Research Centre
Journal or Publication Title: Journal of Organic Chemistry
Publisher: American Chemical Society
Refereed: Yes
ISSN: 00223263
Depositing User: H Kenna
Date Deposited: 07 Aug 2007 14:51
Last Modified: 20 Aug 2013 16:45
URI: http://usir.salford.ac.uk/id/eprint/149

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