Practical synthesis of blepharismone, a mating inducing pheromone of Blepharisma japonicum

Abstract

Both enantiomers of blepharismone, a mating inducing pheromone produced by type II cells of Blepharisma japonicum, were synthesized via the Stille cross-coupling reaction of [4-( tert-butyl-dimethyl-silanyloxy)-2-trimethylstannanyl-phenyl]-carbamic acid tert-butyl ester with an acid chloride derived from ( S)- and ( R)-malic acid as a key reaction. The mating inducing activity of synthetic ( S)-blepharismone was as effective as that of the natural one. The enantiomer ( R)-blepharismone showed no mating inducing activity.