Pheromone synthesis; CXXXIX. Enzymatic preparation of (2S,3R)-4-acetoxy-2,3-epoxybutan-1-ol and its conversion to the epoxy pheromones of the gypsy moth and the ruby tiger moth

Article abstract of DOI:10.1055/s-1992-26290

Pig pancreatic lipase-catalyzed asymmetric hydrolysis of 1,4-diacetoxy-cis-2,3-epoxybutane yielded (2S,3R)-4-acetoxy-2,3-epoxybutan-1-ol, which was converted to two naturally occurring epoxides: the gypsy moth pheromone, disparlure [(7R,8S)-7,8-epoxy-2-methyloctadecane] and the ruby tiger moth pheromone [(6Z,9S,10R)-9,10-epoxy-6-henicosene].