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Synthesis of deuterated fatty acids to investigate the biosynthetic pathway of disparlure, the sex pheromone of the Gypsy Moth, Lymantria dispar
Author(s) -
Abad JoséLuis,
Fabriàs Gemma,
Camps Francisco
Publication year - 2004
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-004-1244-0
Subject(s) - wittig reaction , lymantria dispar , aldehyde , chemistry , stereochemistry , pheromone , alkyne , ylide , sex pheromone , organic chemistry , catalysis , biology , botany , lepidoptera genitalia
The preparation and characterization of a series of deuterium‐labeled intermediates used in the study of the biosynthetic pathway for disparlure, the sex pheromone of Lymantria dispar , is reported. The synthetic route starts with propargyl alcohol, and the deuterium atoms are introduced by deuteration of an alkyne precursor in the presence of Wilkinson's catalyst. The olefinic bond was created by the Wittig reaction of a suitable aldehyde with a common tetradeuterated phosphonium ylide intermediate. The presence of the expected label and its correct location were confirmed by both MS and 13 C NMR. These compounds were successfully used to elucidate the disparlure biosynthetic pathway.