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Synfacts 2011(11): 1154-1154  
DOI: 10.1055/s-0031-1289257
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of HSD-016

Contributor(s): Philip Kocienski
Z.-K. Wan*, E. Chenail, H.-Q. Li, C. Kendall, Y. Wang, S. Gingras, J. Xiang, W. W. Massefski, T. S. Mansour, E. Saiah
Pfizer Inc., Cambridge, USA
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Publication History

Publication Date:
19 October 2011 (online)

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Significance

Cortisol stimulates hepatic glucose production and suppresses insulin-mediated glucose uptake in adipose tissues and muscle. HSD-016 inhibits the conversion of cortisone into cortisol by 11β-hydroxysteroid dehydrogenase (11β-HSD1). It is under development for the treatment of type 2 diabetes. A Sharpless asymmetric dihydroxylation was used to construct the tertiary alcohol in compound J.