Practical Synthesis of (9S,10R)‐9,10‐epoxy‐(3Z,6Z)‐henicosadiene: The Major Pheromone of the Saltmarsh Caterpillar moth Estigmene acrea

An efficient synthesis of (3Z,6Z)-cis-9,10-epoxy-3,6-henicosadiene (1), the major component of sex pheromone of saltmarsh caterpillar moth Estigmene acrea (Drury), was accomplished from commercially available pentadec-3-yn-1-ol and bromoundecane. Chirality was introduced by employing Sharpless asymmetric dihydroxylation on cis-olefin intermediate in the synthesis of 1, for the first time. The other key reactions include metal-dissolving coupling, Lindlar's catalyst-assisted partial hydrogenation, one-pot, three-step epoxidation from vicinal diol, and Wittig olefination. The overall yield of 1 was 24.7% in eight steps. The efficiency and simplicity of this synthesis allow the potential use of pheromone 1 in pest management programs.