Radical mediated stereoselective synthesis of meso-7,11-dimethylheptadecane, a female sex pheromone component of the spring hemlock looper and the pitch pine looper

meso-7,11-Dimethylheptadecane, a female sex pheromone component of the spring hemlock looper and the pitch pine looper, was synthesized from ethyl 2-(bromomethyl)propenoate in nine steps and 14% overall yield. The key step in the synthesis is the highly diastereoselective chelation-controlled radical reaction of diethyl 4-benzyloxy-2,6-dimethyleneheptanedioate with pentyl iodide performed in the presence of 6 equiv of MgBr₂·OEt₂.