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Synfacts 2006(11): 1095-1095  
DOI: 10.1055/s-2006-949394
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a Cathepsin K Inhibitor

Contributor(s): Philip Kocienski
A. Roy*, F. Gosselin, P. D. O’Shea, C-y. Chen
Merck Frosst Centre for Therapeutic Research, Kirkland, Canada and Merck Research Laboratories, Rahway, USA
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Publication History

Publication Date:
24 October 2006 (online)

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Significance

Cathepsin K is a cysteinyl protease that is overexpressed in osteoclasts. Its inhibition is regarded as a potential treatment for osteoporosis. The brief synthesis of the potent cathepsin K inhibitor depicted above features a highly diastereoselective addition of an aryllithium to the α-tri­fluoromethyl imine B performed on a 1.5-mol scale.