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Asymmetric dihydroxylation and hydrogenation approaches to the enantioselective synthesis of R-(+)-α-lipoic acid

✍ Scribed by T.T Upadhya; M.D Nikalje; A Sudalai

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
81 KB
Volume
42
Category
Article
ISSN
0040-4039

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✦ Synopsis

The asymmetric synthesis of methyl (S)-6,8-dihydroxyoctanoate ( ) and (S)-6,8-dimethylsulfonyloxyoctane-1-carboxylic acid (13), key precursors to R-(+)-a-lipoic acid (6) is described using OsO 4 -catalyzed asymmetric dihydroxylation and Ru-catalyzed asymmetric hydrogenation, respectively, as the key steps in the reaction sequence. These methods lead to an efficient formal synthesis of R-(+)-a-lipoic acid in 90% ee.

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