Stereoselective total synthesis of some insect pheromones: (±)-serricornine and (±)-invictolide

Abstract

An efficient (12 steps, 12% overallyield) and stereoselective total synthesis of (±)-serricornine (1) the sex pheromone of the cigarette beetle (Lasioderma serricornine F) is described. The preparation of intermediate 5, which encompasses the proper relative configuration of three contiguous chiral centers of (±)-invictolide, (3), is discussed.

total synthesis; (±)-serricornine; (±)-invictolide; pheromones