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Synfacts 2010(6): 0623-0623
DOI: 10.1055/s-0029-1219849
DOI: 10.1055/s-0029-1219849
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of (-)-Ranirestat
B. M. Trost*, M. Osipov, G. Dong
Stanford University, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
20. Mai 2010 (online)
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.