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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...
To study the activity of the different desaturases present in the pheromone biosynthetic pathway of the Egyptian armyworm, Spodoptera littoralis, we prepared a series of mono-and gem-difluorinated analogs of myristic acid with halogen substitution at the C8–C11 positions of the aliphatic chain via specifically positioned dithiane precursors. Thus, transformation of dithianes by treatment with N-bromosuccinimide...
Lipidic extracts of Spodoptera littoralis pheromone glands submitted to acid methanolysis using: (i) sulfuric acid/methanol/benzene (0.1∶4∶2, by vol) at 90°C for 1 h; (ii) 12 N HCl/methanol (1∶2; vol/vol) at 90°C for 1 h, or (iii) 14% BF3-MeOH at 90°C for 1 h did not reveal the presence of either 11- or 12-hydroxytetradecanoic acid in the extracts, as concluded from the gas chromatography-mass spectrometry...
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