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Synthesis of (-)-Silvestrol
B. Gerard, R. Cencic, J. Pelletier, J. A. Porco, Jr.*
Boston University, USA and McGill University, Montreal, Canada
23 January 2008 (online)
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.