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.

Full text not available from this repository. (Request a copy)

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:	27 Sep 2011 12:30
URI:	http://usir.salford.ac.uk/id/eprint/149

Actions (login required)

Edit record (repository staff only)