Download PDF
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
Enantioselective Synthesis of the Complex Rocaglate (-)-Silvestrol
Angew. Chem. Int. Ed.  2007,  46:  7831-7834  
Crossref
Further Information

Publication History

Publication Date:
23 January 2008 (online)

 PDF Download Permissions and Reprints

Key words

Baker-Venkataraman rearrangement - Mitsunobu reaction - [3+2] photocycloaddition

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.

Comment

A Mitsunobu reaction between F and 1,4-dioxanyl fragment G using fluorous-tagged triphenylphosphine, followed by hydrogenation using Pearlman’s catalyst, delivered (-)-silvestrol. A similar strategy was followed by Rizzacasa and co-workers for the synthesis of (-)-silvestrol and (-)-episilvestrol (Angew. Chem. Int. Ed. 2007, 46, 7835.

   Permissions and Reprints