A NEW APPROACH TO THE SYNTHESES OF THE PHEROMONES OF JAPANESE BEETLE AND BONTEBOK WITH(Z)-VINYL CUPRATES

The dl-form of the sex pheromone of Japanese b(?)tle and the trail pheromone of Bontebok were synthesised in high purity of (Z)-olefinic configuration. The key step of the syntheses of compounds (1) and (2) involved stereospecific addition of n-alkyl cuprates to acetylene followed by addition of vinyl cuprates to aldehyde (7) and 3-buten--2-one.