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Synfacts 2010(6): 0623-0623  
DOI: 10.1055/s-0029-1219849
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (-)-Ranirestat

Contributor(s): Philip Kocienski
B. M. Trost*, M. Osipov, G. Dong
Stanford University, USA
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Publication History

Publication Date:
20 May 2010 (online)

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Significance

Ranirestat is an aldose reductase inhibitor that is in phase III clinical trials for the treatment of hyperglycemia. The key step in the Trost synthesis is the efficient asymmetric allylic alkylation of β-keto ester E mediated by the chiral ligand G. The eight-step synthesis provided (-)-ranirestat in 14% overall yield from the commercial compound A.