A versatile and convenient protocol for the stereocontrolled synthesis of olefinic insect pheromones

Efficient and Stereo-Selective Syntheses of Three Stereoisomers of the Sex Pheromone of the Cowpea Weevil,Callosobruchus maculatus

“…The one-pot oxidation employed in the preparation of 6 would be an efficient mild oxidation procedure for converting alcohols to acids. The stereoselective syntheses of 2Z (5), [17][18][19] methylene (6) 9,20-23) and 3Z (6) 24,25) have been reported, but the stereoselective syntheses of 2E (2) and 3E (5) have not previously been reported. This is therfore the first example of the stereoselective synthesis of 3E (5).…”

Access to 2,4-Dien-6-ynoic Acid Esters Using Selenium Chemistry. Formal Synthesis of Z,Z-Dodeca-3,6-dien-1-ol (Trail Pheromone Mimic of the Subterranian Termite Reticulitermes virginicus) and Z,Z-Dodeca-3,6-dien-11-olide (Aggregation Pheromone of the Grain Beetles Oryzaephilus mercartor and O. surinamensis)

“…13 C NMR data were in good agreement with the literature. 2 Methyl 11-oxododeca-2,4-dien-6-ynoate 1b. Compound 1b was prepared by the similar oxidation of methyl 2-(4-methoxyphenylseleno)-11,11-ethylenedioxydodec-4-en-6-ynoate (0.200 g, 0.443 mmol) with H 2 O 2 in THF.…”

Biocatalysis Applied to the Synthesis of Pheromones

“…In addition, Vasilev et al [181] reported the chemoenzymatic synthesis of several acidic insect pheromones. For example, (Z)-dec-3-enoic acid (40), the aggregation pheromone of the furniture carpet beetle Anthrenus flavipes (Dermestidae), otherwise known as the 'museum beetle', was obtained with 99% ee; the key step in the synthesis was the PPL-catalyzed hydrolysis of the corresponding ester.…”