Affiliation
CRC Drug Development Group and CRC Radiochemical Targeting and Imaging Group, Paterson Institute for Cancer Research, Christie Hospital NHS Trust, Manchester, M20 4BX, U.K.Issue Date
2001-11-30
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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
Novel syntheses of cis and trans isomers of combretastatin A-4. 2001, 66 (24):8135-8 J. Org. Chem.Journal
The Journal of Organic ChemistryDOI
10.1021/jo015959zPubMed ID
11722216Type
ArticleLanguage
enISSN
0022-3263ae974a485f413a2113503eed53cd6c53
10.1021/jo015959z
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