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.
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: | 20 Dec 2018 09:40 |
| URI: | http://usir.salford.ac.uk/id/eprint/149 |
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