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The stereoselective total synthesis of (+)-18-(6S,9R,10R)-bovidic acid

✍ Scribed by J.S. Yadav; K. Ramesh; U.V. Subba Reddy; B.V. Subba Reddy; Ahamad Al Khazim Al Ghamdi

Publisher: Elsevier Science
Year: 2011
Tongue: French
Weight: 319 KB
Volume: 52
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2011.03.089

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✦ Synopsis

An expedient stereoselective total synthesis of 18-carbon (+)-(6S,9R,10R)-bovidic acid, isolated from the pelage and skin of a gaur B. frontalis is described using L-proline catalysed sequential a-aminoxylation and Horner-Wadsworth-Emmons olefination of aldehyde, cross metathesis and tandem Sharpless asymmetric dihydroxylation-S N 2 cyclization reaction as the key steps.

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