Selective transformation reaction of 6,8-dioxabicyclo[3.2.1]octane structure to δ,ε-enone and application to the synthesis of Douglas-fir tussock moth pheromone

Lewis acid induced C–O bond cleavage of a bicyclic ketal compound using AcCl–NaI produced a mixture of δ,ε-enone, allylic acetate and diacetate derivatives via a common 5-membered acetoxonium intermediate. A selective method to the synthesis of δ,ε-enone in high yield was introduced and applied to the synthesis of Douglas-fir tussock moth pheromone.