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Synfacts 2013; 9(10): 1033
DOI: 10.1055/s-0033-1339715
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of AMG 837

Contributor(s):
Philip Kocienski
Hamilton JY, Sarlah D, Carreira EM * ETH Zürich, Switzerland
Iridium-Catalyzed Enantioselective Allylic Alkynylation.

Angew. Chem. Int. Ed. 2013;
52: 7532-7535
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Further Information

Publication History

Publication Date:
17 September 2013 (online)

 
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Key words

AMG 837 - GPR40 receptor agonist - asymmetric alkynylation - asymmetric substitution - iridium - allylic alcohols - potassium alkynyltrifluoroborates

Significance

A new versatile method for the iridium-catalyzed asymmetric substitution of racemic allylic alcohols is exemplified by the depicted synthesis of AMG 837, a GPR40 receptor agonist that is of interest for the treatment of type 2 diabetes.


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Comment

The allylic alkynylation (27 examples) typically provides excellent branched-to-linear regioselectivity (rr > 50:1) and high enantioselectivity (≥99%). The scope of the allylic alkynylation was explored using 12 allylic alcohols and 15 potassium alkynyltrifluoroborates.


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