Synthesis Elongateof ( R , Z ) - 7 , 15 - Hexadecadien - 4 - olide , Chafer ( " eptop ] ij , lla picea )

Leal et aL have recently reported the isolation of the sex pheromone of the yellowish elongate chafer, Heptophylla picea Motshulsky (Coleoptera, Scarabaeidae, Mololonthinae), an important agricultural pest. especially for tea and fiower production.i) They deduced its structure to be (Z)-7.15-hexadecadien-4-oljde (1> t'rom the mass and infrared spectral data of the pheromone and jts derivatives (Fig. i). Our enantioselective synthesis of (R,Z)-7,15hexadecadien-4-olidc [(R)-!] f'rom L-malic acid was accomplished, and the identity of the synthetic pheromone against the natural inateria; was established by comparing their mass and infvared spectra, as well as their biological activities. V'urthermore, GLC analyscs of samples of 4-hexadccanolide prepared by catalytic hydrogenation of