Synthesis of (4R)-Methylnonan-1-ol and (4R,8RS)-Dimethyldecanal from (S)-(+)-3,7-Dimethyl-1,6-octadiene

Optically active (4R,8RS)-dimethyldecanal, an analog of the aggregation pheromone of the flour beetles Tribolium confusum and T. Castaneum, and (4R)-methylnonan-1-ol, the sex pheromone of the yellow mealworm Tenebrio molitor L., are synthesized using ozonolytic transformation of (6R,10)-dimethyl-9-undecen-2-one to (6R)-methyl-9-hydroxynonan-2-one in the key step. The starting compound is available as enantiomerically enriched (ee ~50%) (S)-(+)-3,7-dimethyl-1,6-octadiene.