3,3]Sigmatropic ring expansion of cyclic thionocarbonates. 12. synthesis of (−)-yellow scale pheromone

Abstract

(−)-Yellow scale pheromone 1 has been synthesized by the route via [3,3]sigmatropic ring expansion of the 8-membered thionocarbonate 3 containing a diene moiety. The key Z-10-membered intermediate 2 was exclusively synthesized by a one-pot conversion from a chiral aldehyde (+)- 4 and a dienyliodide 14.