STUDIES ON THE SEX PHEROMONE——SYNTHESIS OF(E)-9-TETRADECEN-1-YL ACETATE

<正> (E)-9-tetradecen-l-yl acetate (10) is the main component of Bryotopha similis sexpheromone.Its synthesis has been reported,but these routines are complicated and thestereosdectivities are poor.Here we report a new synthetic method.Via a three-stepprocess,we got (E)-3-octene-l-ol (5)with 100% stereochemical purity,from availabletetrahydrofuran to open up the ring of 2-butyl-3-chlorotetrahydrofuran (3) with potassiumfor the first time.Its bromide (7) was coupled with Grignard reagent (8) at the catalysis ofCuI to provide the key intermediate (9).The intermediate (9) was depyranylated and then