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A Convenient Synthesis of (4R,7Z,11Z)-(-)-4-Methylheptadeca-7,11-dienal and (4R,7Z,11Z)-4-Methylheptadeca-7,11-dienoic Acid

✍ Scribed by Sharma, Anubha ;Chattopadhyay, Subrata

Publisher: John Wiley and Sons
Year: 2006
Tongue: English
Weight: 330 KB
Volume: 1996
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199619960411

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✦ Synopsis

Abstract

A synthesis of the title aldehyde 1 and acid 2, the (R) enantiomers of the antifungal and antibacterial principles of Sporothrix species, was developed. Alkylation of the alkynol derivative 6 with (S)‐citronellyl bromide (5), depyranylation, cis hydrogenation, PCC oxidation, and Z‐selective Wittig reaction with hexylidenephosphorane gave the hydrocarbon 11. Its regioselective epoxidation and cleavage of the epoxide with HlO~4~ affords (R)‐1 which was oxidized to (R)‐2.

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