K Gaukroger
Novel syntheses of cis and trans isomers of combretastatin A-4
Gaukroger, K; Hadfield, JA; Hepworth, LA; Lawrence, NJ; McGown, AT
Authors
JA Hadfield
LA Hepworth
NJ Lawrence
AT McGown
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.
Citation
Gaukroger, K., Hadfield, J., Hepworth, L., Lawrence, N., & McGown, A. (2001). Novel syntheses of cis and trans isomers of combretastatin A-4. Journal of Organic Chemistry, 66(24), 8135-8138. https://doi.org/10.1021/jo015959z
Journal Article Type | Article |
---|---|
Publication Date | Nov 2, 2001 |
Deposit Date | Aug 7, 2007 |
Journal | Journal of Organic Chemistry |
Print ISSN | 0022-3263 |
Publisher | American Chemical Society |
Peer Reviewed | Peer Reviewed |
Volume | 66 |
Issue | 24 |
Pages | 8135-8138 |
DOI | https://doi.org/10.1021/jo015959z |
Publisher URL | http://dx.doi.org/10.1021/jo015959z |
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