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Synfacts 2011(6): 0586-0586  
DOI: 10.1055/s-0030-1259892
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of AMG 837

Contributor(s): Philip Kocienski
R. Yazaki, N. Kumagai*, M. Shibasaki*
Institute of Microbial Chemistry, Tokyo and The University of Tokyo, Japan
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Publication History

Publication Date:
19 May 2011 (online)

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Significance

Agonists of the G-protein-coupled receptor GPR40 amplify insulin secretion from the pancreas. AMG 837 (J) is a GPR40 agonist that is a potential treatment for type-2 diabetes. Shibasaki and co-workers report a short, enantio­selective synthesis of AMG 837 that features an asymmetric conjugate addition of ethynyltrimethylsilane (B) to the α,β-unsaturated thioamide A promoted by a soft Lewis acid/hard Brønsted base cooperative catalyst.