A synthesis of Gf-Serricornin is described. The (4S,SSI4methyl-5-ethyl Gvalerolactone 8 has been synthesized with a high degree of enantioselectivity starting from (R)-(+)-(E jl-propenyl ptolylsulfoxide 2, having the enantkxelective Marino's lactonization as the key step. A number of stereoselective syntheses of senicomin, the sex pheromone of the cigarette beetle &rsioderma serricorne F.), have been reported in the last few years.1 'Ihe most active stereoisomer of this dass of pheromones has been shown to be the (4S,G,7SKsomer2 (1) through a series of structure-activity studies. In this paper we report the synthesis of (4SJSt4_methyl-!5-ethyl Gvalerolactone 6, with a high degree of enandoselectivity. Lactone 8 has already been transformed into Serricornin by Sate and c0worlcers.f The critical step in our synthesis for installing the chiral centers involves an enantioselective lactonization reaction of optically active vinyl sulfoxides, discovered by one of us.4 The overall synthetic plan is outlined in scheme 1.
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