Pheromone Synthesis, CXLIX. Synthesis of (2E,4E,6R,10S)‐4,6,10‐Trimethyl‐2,4‐dodecadien‐7‐one – the Major Component of the Sex Pheromone of the Maritime Pine Scale (Matsucoccus feytaudi) – and its Three Stereoisomers

Abstract (2E,4E,6R,10S)‐4,6,10‐Trimethyl‐2,4‐dodecadien‐7‐one (1) – the major component of the sex pheromone of the maritime pine scale – and its three stereoisomers were synthesized by starting from (R)‐ or (S)‐citronellol (4) and employing the asymmetric epoxidation (9 → 10) and the palladium‐catalyzed reductive cleavage of the epoxy ring (13 → 14) as the key steps.