A novel synthesis of (S)- and (R)-1-methyl-2-cyclohexen-1-ol, aggregation pheromones of Dendroctonous pseudotsugae

Dendroctonous pseudotsugae is better known as the Douglas-fir beetle. This species possesses a striking pheromone system which is found in the female beetle. The system is a complex mix of substances and is composed primarily of (S)- and (R)-1-methyl-2-cyclohexen-1-ol of unknown enantiomeric composition. These compounds are the subject of a new methodology, now used for synthesizing analogs of these natural pheromones, which is reported on.