Abstract:

Seudenol (3-methyl-2-cyclohexen-1-ol) is an aggregation pheromone isolated from female hindguts of the Douglas fir beetle, ^{Dendroctonus pseudotsugae},by Vité^[l]. Sivlerstein reported that the natural seudenol is racemic^[2]. Racemic seudenols have been synthesized by various methods^[3-5], almost all of which have used 3-methyl-2-cyclohexen-1-one (4) as precursor or intermediate, followed by reduction. Among reduction of enone (4), most systems studied to date have focused on selective reduction of α, β-unsaturated ketone to the corrsponding allylic alcohol. But most of the reduction required special and expensive reagent^[3-5]. In this paper,a new convenient material route was reported to synthesize (±)-seudenol. The route is illustrated in the following scheme.