An Efficient and Stereoselective Total Synthesis of (+/-)-Serricornine

Abstract An efficient and stereoselective total synthesis of (+/-)-serricornine (1) the sex pheromone produced by the female cigarette beetle Lasioderma serricorne F, is described. (3SR, 5SR, 6SR)-6-Ethyltetrahydro-3,5-dimethyl-2H-pyran-2-one (10) is prepared in 65% yield through lactonization of a 1:1 mixture of C-2 epimers of the corresponding esters.