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

Insect pheromone synthesis in Brazil: an overview

“…[21][22][23][24] Its absolute configuration was definitively established by Mori and co-workers 25,26 as (4S, 6S, 7S)-6. Pilli and Murta 27,28 described an efficient 12 step diastereoselective synthesis of (±)-6, in 12% overall yield (Scheme 2). Ferreira et al described a formal and enantioselective synthesis of (4S,6S,7S)-(-)-serricornin (6).…”