A concise enantioselective synthesis of (-)-ranirestat.
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.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305, USA. bmtrost@stanford.edu
Osipov
Maksim
M
Dong
Guangbin
G
D000449:Aldehyde Reductase / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011719:Pyrazines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011719:Pyrazines; D013141:Spiro Compounds; D000449:Aldehyde Reductase; C115070:ranirestat