Short Syntheses of Unsaturated Aliphatic Ketone Pheromones

Abstract

While most pheromones of Lepidoptera are unsaturated aldehydes, alcohols or acetates with the oxidated carbon usually being the first carbon of the aliphatic chain, there are some pheromone examples where an intermediate carbon other than the first one is present in an oxidized state. Such is the case of the pheromone of the peach fruit moth, Carposina niponensis, a mixture of (Z)-7-eicosen-11-one and (Z)-7-nonadecen-11-one¹ and of the Douglas fir tussock moth, Orgya pseudotsugata, for which a single component, (Z)-6-heneicosen-11-one, has been isolated².