Absolute configuration of (−)-4-methylheptan-3-ol, a pheromone of the smaller european elm bark beetle, as determined by the synthesis of its (3 R,4 R)-(+)- and (3 S,4 R)-(+)-isomers

Abstract

Nerol and geraniol were stereoselectively converted to (±)- threo- and (±)- erythro-4-methylheptan-3-ol respectively. ( R)-(+)-Citronellic acid was converted to a mixture of (3 R,4 R)-(+)- threo- and (3 S,4 R)-(+)- erythro-isomers which was separable by GLC. These syntheses established the absolute configuration of the naturally occurring (−)-4-methylheptan-3-ol to be 3 S,4 S.