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

Gaukroger, K, Hadfield, JA ORCID: https://orcid.org/0000-0001-7984-8319, 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:	Schools > School of Environment and Life Sciences Schools > School of Environment and Life Sciences > Biomedical Research Centre
Journal or Publication Title:	Journal of Organic Chemistry
Publisher:	ACS Publications
Refereed:	Yes
ISSN:	00223263
Depositing User:	H Kenna
Date Deposited:	07 Aug 2007 13:51
Last Modified:	27 Aug 2021 21:58
URI:	http://usir.salford.ac.uk/id/eprint/149

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