Financial support from the National Institutes of Health (GM-073855 and P50 GM067041), Wyeth Pharmaceuticals, Merck Research Laboratories, and the NCI intramural research program is gratefully acknowledged. We thank the Developmental Therapeutics Program at the NCI for the 60-cell assay, ThalesNano, Inc. (Budapest, Hungary) for assistance with the continuous-flow hydrogenation reactor, and Prof. Dr. Corey Stephenson (Boston University) for helpful discussions.
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Communication
Enantioselective Synthesis of (+)-Chamaecypanone C: A Novel Microtubule Inhibitor†
Article first published online: 12 JAN 2009
DOI: 10.1002/anie.200805486
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Dong, S., Hamel, E., Bai, R., Covell, David G., Beutler, John A. and Porco, John A. (2009), Enantioselective Synthesis of (+)-Chamaecypanone C: A Novel Microtubule Inhibitor. Angew. Chem. Int. Ed., 48: 1494–1497. doi: 10.1002/anie.200805486
- †
Publication History
- Issue published online: 30 JAN 2009
- Article first published online: 12 JAN 2009
- Manuscript Received: 10 NOV 2008
Funded by
- National Institutes of Health. Grant Numbers: GM-073855, P50 GM067041
- Wyeth Pharmaceuticals
- Merck Research Laboratories
Keywords:
- cycloaddition;
- cyclopentadienone;
- microtubule inhibitor;
- natural product;
- total synthesis
Abstract
A bicycle built for tubulin: The total synthesis of (+)-chamaecypanone C has been achieved by using a tandem retro-Diels–Alder/Diels–Alder cascade reaction (see scheme). Initial biological studies demonstrate that (+)-chamaecypanone C is an inhibitor of tubulin assembly and binds at the colchicine site.