Insect pheromones. Synthesis of chiral sex pheromone components of several species of Trogoderma (Coleoptera: Dermestidae)

The (S)-enantiomers of (Z)- and (E)-14-methyl-8-hexadecen-1-ol, 1 and 4, respectively, and of (Z)- and (E)-14-methyl-8-hexadecenal, 6 and 7, respectively, which are sex pheromone components of dermestid beetles, have been synthesized in high optical purity starting from optically pure (S)-2-methyl-1-butanol. The preparation of 1 has been carried out using a new general method for reducing stereoselectively and in high yield ω-alkynols to the corresponding (E)-alkenols. The rotatory power of optically pure 1, 4, 6 and 7 has been established.