Synthesis of (3R)‐3‐Hydroxy‐2‐Hexanone, (2R,3R)‐2,3‐hexanediol and (2S,3R)‐2,3‐hexanediol, the Male Sex Pheromone of Hylotrupes bajulus and Pyrrhidium sanguineum (cerambycidae)

The following compounds were identified as male pheromone components of the longhorn beetles Hylotrupes bajulus and Pyrrhidium sanguineum: (3R)‐3‐hydroxy‐2‐hexanone [(3R)‐1], (2S,3R)‐2,3‐hexanediol [(2S,3R)‐4] and (2R,3R)‐2,3‐hexanediol [(2R,3R)‐4]. The syntheses of enantiomerically pure samples, enantiomeric separation by chiral gas chromatography and unambiguous structure assignment of the target compounds are described.