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

K Gaukroger, JA Hadfield, LA Hepworth…

Index: Gaukroger, Keira; Hadfield, John A.; Hepworth, Lucy A.; Lawrence, Nicholas J.; McGown, Alan T. Journal of Organic Chemistry, 2001 , vol. 66, # 24 p. 8135 - 8138

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Citation Number: 166

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. ...

~5%

Environmentally friendly homocoupling reaction of functional...

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