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A concise enantioselective synthesis of (-)-ranirestat.

ABSTRACT: A concise, enantioselective synthesis of the potent aldose reductase inhibitor ranirestat (1) is reported. The synthesis was accomplished employing inexpensive, commercially available starting materials. A palladium-catalyzed asymmetric allylic alkylation (Pd-AAA) of malonate 4 was utilized as a key transformation to construct the tetrasubstituted chiral center in the target.

SUBMITTER: Trost BM 

PROVIDER: S-EPMC2850125 | biostudies-literature | 2010 Mar

REPOSITORIES: biostudies-literature

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A concise enantioselective synthesis of (-)-ranirestat.

Trost Barry M BM   Osipov Maksim M   Dong Guangbin G  

Organic letters 20100301 6

A concise, enantioselective synthesis of the potent aldose reductase inhibitor ranirestat (1) is reported. The synthesis was accomplished employing inexpensive, commercially available starting materials. A palladium-catalyzed asymmetric allylic alkylation (Pd-AAA) of malonate 4 was utilized as a key transformation to construct the tetrasubstituted chiral center in the target. ...[more]

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