Improved preparations of alkyne nitriles, acetates, and alcohols : Application to the synthesis of the sex pheromone components of the Douglas fir tussock moth and peach fruit moth.

One-pot conversions of terminai alkynes to cyanoethylated and cyanopropylated alkynes are described. Reactions of these nitriles with Grignard reagents produced alkynones, the reductions of which gave alkenones. The described routes provide 3-step syntheses of several insect sex or stimulatory pheromones, namely, those of the peach fruit moth (Carposina niponensis Walsingham), Douglas fir tussock moth (Orgyia pseudotsugata [McDunnough]), and housefly (Musca domestica L.). Additionally, potentially useful one-pot processes for the preparation of hydroxyalkylated and acetoxyalkylated alkynes are reported.