PHEROMONE SYNTHESIS .157. SYNTHESIS OF THE ENANTIOMERS OF SYN-4-METHYL-5-NONANOL TO DETERMINE THE ABSOLUTE-CONFIGURATION OF THE NATURALLY-OCCURRING (4S,5S) ISOMER ISOLATED AS THE MALE-PRODUCED PHEROMONE COMPOUND OF RHYNCHOPHORUS-VULNERATUS AND METAMASIUS-HEMIPTERUS

The enantioselective synthesis of both (4R,5R)- and (4S,5S)-4-methyl-5 -nonanol (1) was achieved by starting from an optically active epoxide 5. A GC comparison on a chiral stationary phase of the synthetic enan tiomers of 1 with the naturally occurring 1 was executed, and (4S,5S)- 1 was shown to be identical with the natural 1 isolated as the male-pr oduced pheromone compound of the weevils Rhynchophorus vulneratus and Metamasius hemipterus.