Stereochemical studies on pheromonal communications.

Pheromonal communications are heavily dependent on the stereochemistry of pheromones. Their enantioselective syntheses could establish the absolute configuration of the naturally occurring pheromones, and clarified the unique relationships between absolute configuration and bioactivity. For example, neither the (R)- nor (S)-enantiomer of sulcatol, the aggregation pheromone of an ambrosia beetle, is behaviorally active, while their mixture is bioactive. Recent results as summarized in the present review further illustrate the unique and diverse relationships between stereochemistry and bioactivity of pheromones.