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Synfacts 2009(8): 0829-0829  
DOI: 10.1055/s-0029-1217508
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Chamaecypanone C

Contributor(s): Philip Kocienski, Stewart Eccles
S. Dong, E. Hamel, R. Bai, D. G. Covell, J. A. Beutler, J. A. Porco Jr.*
Boston University and National Cancer Institute at Frederick, USA
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Publication History

Publication Date:
23 July 2009 (online)

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Significance

(+)-Chamaecypanone is one of several bicyclo[2.2.2]octenone natural products that have been isolated from Chamaecyparis obtuse var. formosana. (+)-Chamaecypanone has good activity (IC50 = 190nM) against human epidermoid carcinoma. The authors describe a retro-Diels-Alder/Diels-Alder pathway to the natural product.