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Synfacts 2008(2): 0121-0121  
DOI: 10.1055/s-2007-992506
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Silvestrol

Contributor(s): Philip Kocienski, Indu Dager
B. Gerard, R. Cencic, J. Pelletier, J. A. Porco, Jr.*
Boston University, USA and McGill University, Montreal, Canada
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Publication History

Publication Date:
23 January 2008 (online)

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Significance

Silvestrol, isolated from the Aglaia foveolata, possesses cytotoxic activity comparable to paclitaxel. The first enantioselective synthesis of silvestrol is reported here; it involved an enantioselective [3+2] photocycloaddition of an oxidopyrylium ylide derived from excited-state intramolecular proton transfer of 3-hydroxyflavone C using a chiral Brønsted acid D.