SYNTHESIS OF A FLUORINATED ANALOG OF THE SEX PHEROMONE OF THE PROCESSIONARY MOTH Thaumetopoea pityocampa

Article abstract of DOI:10.1016/S0040-4020(01)87329-4

The synthesis of (E)-13-fluorohexadec-13-en-11-ynil acetate 1, a fluorinated analog of the sex pheromone of the processionary moth Thaumetopoea pityocampa is described.The synthetic scheme involves epoxidation of the double bond, regioselective opening of the oxirane ring with Olah's reagent, tosylation of the resulting fluorohydrin and dehydrotosylation.Structural features of the intermediate diastereomeric fluorohydrins 4a and 4b and tosylates 5a and 5b are also discussed on the basis of their 1 H and 19 F NMR spectra.