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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 39, 2009 - Issue 4
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Original Articles

New and Concise Approach to (R)-α-Lipoic Acid

, , &
Pages 691-701 | Received 20 Mar 2008, Published online: 27 Jan 2009
 

Abstract

A concise enantiospecific synthesis of (S)-6,8-bis(methylsulfonyloxy)-octanoic acid (2), a ready precursor of (R)-(+)-α-lipoic acid (1), is reported. The key step of the synthesis is the coupling of the tosylate derived from (R)-malic acid with phenylpropyl magnesium bromide. A recently reported green procedure was used for the oxidative unmasking of the phenyl group, used as a latent carboxyl group.

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