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Stereoselective synthesis of (5 R ,6 S )‐6‐acetoxy hexadecanolide—The major component of the oviposition attractant pheromone of the mosquito Culex pipens fatigans and its enantiomer from L ‐glutamic acid
Author(s) -
Ding Yu,
Li JiaYao,
Wang ZhiQin
Publication year - 1992
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.19920100512
Subject(s) - chemistry , pheromone , stereochemistry , ring (chemistry) , stereoselectivity , sex pheromone , lactone , botany , organic chemistry , catalysis , biology
A concise synthesis of the mosquito oviposition attractant pheromone, (‐)(5 R , 6 S )‐and (+)‐(5 S , 6 R )‐6‐acetoxy hexadecanolide from L ‐glutamic acid is described. The key steps are the inversion of the configuration at C‐4 of 7, and the formation of δ ‐lactone from the γ ‐lactone through ring enlargement.