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Synfacts 2010(6): 0621-0621  
DOI: 10.1055/s-0029-1219848
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a Dipeptidyl Peptidase IV Inhibitor

Contributor(s): Philip Kocienski
F. Xu*, E. Corley, M. Zacuto, D. A. Conlon, B. Pipik, G. Humphrey, J. Murry, D. Tschaen
Merck Research Laboratory, Rahway, USA
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Publication History

Publication Date:
20 May 2010 (online)

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Significance

The target molecule is a lead dipeptidyl peptidase IV (DPP-4) inhibitor for the treatment of type 2 diabetes mellitus. The synthesis depicted delivered multikilogram quantities of the drug candidate in 23% overall yield. The key step is an asymmetric conjugate addition of ­dimethyl malonate to the nitrostyrene B catalyzed by just 1 mol% of the demethylquinidine catalyst C.