3,3]Sigmatropic ring expansion of cyclic thionocarbonates. 9. total synthesis of (±)-yellow scale pheromone via 10-membered thiolcarbonate

Abstract

(±)-Yellow scale pheromone 1 has been synthesized via the route illustrated in Scheme 1. The [3,3]sigmatropic ring expansion of 8-membered thionocarbonate 4 exclusively produced the (Z)-10-membered thiolcarbonate 3, which was transformed via three steps to the intermediate 2 with all the necessary carbon atoms for the pheromone. Reductive removal of the SCO moiety in 2 followed by acetylation gave 1.