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Synfacts 2010(9): 0975-0975  
DOI: 10.1055/s-0030-1257873
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Casopitant

Contributor(s): Philip Kocienski
S. K. Lee, U. K. Tambar, N. R. Perl, J. L. Leighton*
Columbia University, New York, USA
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Publication History

Publication Date:
23 August 2010 (online)

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Significance

Casopitant (Zunrisa®) is a neuro­kinin-1 receptor antagonist being developed for the treatment of chemotherapy-induced nausea. A key step in the small-scale synthesis depicted is the construction of the piperidine ring in D with the correct (R)-stereochemistry at C2 via a formal asymmetric aza-Diels-Alder reaction between the N-acyl hydrazone A and Danishefsky’s diene (B) mediated by the Lewis acid C. Eight further examples of the reaction are recorded.