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Synthesis 2011(22): 3711-3715  
DOI: 10.1055/s-0030-1260248
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

New Efficient Synthesis of Combretastatin A-4 via Colvin Rearrangement

Ognyan I. Petrov*a, Mariana S. Gerovaa, Christo D. Chaneva, Katya V. Petrovab
a Faculty of Chemistry, University of Sofia St. Kliment Ohridski, 1 James Bourchier Avenue, 1164 Sofia, Bulgaria
Fax: +359(2)9625438; e-Mail: opetrov@chem.uni-sofia.bg;
b Chemistry Department, Vanderbilt University, Nashville, TN 37235-1822, USA
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Publication History

Received 21 July 2011
Publication Date:
29 September 2011 (online)

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Abstract

A new four-step approach for the synthesis of anticancer agent combretastatin A-4 (CA-4) has been developed. The method includes the Colvin rearrangement of the benzophenone derivative phenstatin to the key diarylalkyne followed by stereoselective semi-reduction to CA-4 in good overall yield.

Key words

combretastatin A-4 - phenstatin - Colvin rearrangement - anticancer agents - stilbene