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Synfacts 2009(5): 0470-0470  
DOI: 10.1055/s-0028-1088169
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (+)-Cassaine

Contributor(s): Philip Kocienski, Stewart Eccles
S. Phoenix, M. S. Reddy, P. Deslongchamps*
Université de Sherbrooke, Canada
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Publication History

Publication Date:
22 April 2009 (online)

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Significance

(+)-Cassaine was isolated from the bark of Erythrophleum guineense. It is a nonste­roidal inhibitor of Na+/K+-ATPase. The synthesis hinged on a transannular Diels-Alder reaction to construct the trans-anti-cis tricycle which was converted into the trans-anti-trans ring system in the final step.