Chirality induction and chiron approaches to enantioselective total synthesis of α-lipoic acid

An efficient, short and convenient asymmetric synthesis of (R)-(+)-lipoic acid in seven steps from chiral hydroxy aldehyde with 32.5% overall yield is described. Synthesis of S and R enantiomers of α-lipoic acid from cis-1,4-butene diol derived chiral lactone is reported with 34 % overall yield. The...

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Bibliographic Details
Published in:Tetrahedron 2015-06, Vol.71 (24), p.4213-4218
Main Authors: Chavan, Subhash P., Pawar, Kailash P., Praveen, Ch, Patil, Niteen B.
Format: Article
Language:English
Subjects:
Chiral pool
Chirality induction
Enantioselective
Lipoic acid
Sharpless asymmetric dihydroxylation
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Description
Summary:An efficient, short and convenient asymmetric synthesis of (R)-(+)-lipoic acid in seven steps from chiral hydroxy aldehyde with 32.5% overall yield is described. Synthesis of S and R enantiomers of α-lipoic acid from cis-1,4-butene diol derived chiral lactone is reported with 34 % overall yield. The present synthesis involves use of simple reaction conditions making it a convenient synthesis. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2015.04.090