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Synfacts 2011(2): 0119-0119  
DOI: 10.1055/s-0030-1259212
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Telcagepant

Contributor(s): Philip Kocienski
F. Xu et al.*
Merck Research Laboratories, Rahway, USA
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Publication History

Publication Date:
19 January 2011 (online)

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Significance

Telcagepant is a selective antagonist of calcitonin gene related peptide (CGRP) that is in phase clinical trials for the treatment of migraine. The synthesis featured an enantioselective 1,4-addition of nitromethane, which is the first ­application of iminium organocatalysis (B ♦  D) on an industrial scale and a highly stereoselective Doebner-Knoevenagel condensation that created the enamide F.