Synthesis of deuterated fatty acids to investigate the biosynthetic pathway of disparlure, the sex pheromone of the gypsy moth, Lymantria dispar.
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 13C NMR. These compounds were successfully used to elucidate the disparlure biosynthetic pathway.
Abad
José-Luis
JL
Departamento de Química Orgánica Biológica, Instituto de Investigaciones Químicas y Ambientales de Barcelona, Consejo Superior de Investigaciones Científicas, 08034-Barcelona, Spain. jlaqob@iiqab.csic.es
Fabriàs
Gemma
G
Camps
Francisco
F
D000447:Aldehydes / Q000737:chemistry; D000473:Alkanes / Q000737:chemistry / Q000378:metabolism; D000480:Alkynes / Q000737:chemistry; D000818:Animals; D003903:Deuterium / Q000737:chemistry; D005227:Fatty Acids / Q000138:chemical synthesis* / Q000737:chemistry; D005260:Female; D008297:Male; D015394:Molecular Structure; D009036:Moths / Q000737:chemistry*; D020005:Propanols / Q000737:chemistry; D012724:Sex Attractants / Q000096:biosynthesis / Q000737:chemistry
D000447:Aldehydes; D000473:Alkanes; D000480:Alkynes; D005227:Fatty Acids; D020005:Propanols; D012724:Sex Attractants; C001150:disparlure; D003903:Deuterium; C028255:propargyl alcohol