Financial support from the National Institutes of Health (J.A.P.,Jr., GM-073855) and from the NCI Canada (J.P., 017099), Bristol-Myers Squibb, and Merck Research Laboratories is gratefully acknowledged. We thank Dr. R. Murray Tait for providing natural silvestrol and Dr. Siva Dandapani, Dr. Jean-Charles Marié, Dr. Aaron Beeler, and Mr. Suwei Dong (Boston University) for helpful discussions.
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Communication
Enantioselective Synthesis of the Complex Rocaglate (−)-Silvestrol†
Article first published online: 5 SEP 2007
DOI: 10.1002/anie.200702707
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Gerard, B., Cencic, R., Pelletier, J. and Porco, John A. (2007), Enantioselective Synthesis of the Complex Rocaglate (−)-Silvestrol. Angew. Chem. Int. Ed., 46: 7831–7834. doi: 10.1002/anie.200702707
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Publication History
- Issue published online: 4 OCT 2007
- Article first published online: 5 SEP 2007
- Manuscript Received: 20 JUN 2007
Funded by
- National Institutes of Health. Grant Number: GM-073855
- NCI Canada. Grant Number: 017099
- Bristol-Myers Squibb
- Merck Research Laboratories
Keywords:
- antitumor agents;
- cycloaddition;
- natural products;
- photochemistry;
- total synthesis
The total synthesis of the natural product (−)-silvestrol (1) has been accomplished and features enantioselective [3+2] photocycloaddition of a substituted 3-hydroxyflavone and methyl cinnamate promoted by a chiral Brønsted acid. Initial biological studies indicate a 5–10-fold greater activity of silvestrol as an inhibitor of protein synthesis in HeLa cells than its 1′′′′ diastereomer.