Abstract
(−)-Serricornin, a sex pheromone of a cigarette beetle ( Lasioderma serricorne F.), has been synthesized highly stereoselectively starting from ( Z)-4-benzyloxy-2-buten-1-ol by employing the Katsuki-Sharpless asymmetric epoxidation and two stereospecific methylation reactions, the regioselective γ-methylation of a γ,δ-epoxy acrylate by trimethylaluminum and α-methylation of a δ-lactone, as key steps.
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