Synthesis of the (R)-(-)-enantiomers of the pheromone components of several species of Trogoderma [Coleoptera: Dermestidae]

The chemically pure (R)(-)-enantiomers of (Z)- and (E)-14-methyl-8-hexadecen-1-ol and of (Z)- and (E)-14-methyl-8-hexadecenal, which are sex pheromone components of several species of female dermestid beetles, were synthesised in fairly good overall yield and in rather high optical purity starting from (S)(-)-citronellol. A mixture of (R)(Z)- and (R)(E)-14-methyl-8-hexadecenal in the 92:8 ratio was 107 time less active than a mixture of the corresponding (S)-enantiomers when tested on male Khapra beetles, Trogoderma granarium.