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A Convenient Synthesis of (4 R ,7 Z ,11 Z )‐(‐)‐4‐Methylheptadeca‐7,11‐dienal and (4 R ,7 Z ,11 Z )‐4‐Methylheptadeca‐7,11‐dienoic Acid
Author(s) -
Sharma Anubha,
Chattopadhyay Subrata
Publication year - 1996
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199619960411
Subject(s) - chemistry , regioselectivity , bromide , epoxide , alkylation , wittig reaction , aldehyde , enantiomer , derivative (finance) , medicinal chemistry , antifungal , stereochemistry , organic chemistry , catalysis , medicine , dermatology , financial economics , economics
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 .