Synthesis of exo-brevicomin, the pheromone of western pine beetle, to obtain optically active forms of known absolute configuration

(1R:7R)-(+)-exo-Brevicomin 1 and its antipode 1′ were synthesized from (2S:3S)-D-(−)-tartaric acid 2 and its antipode, respectively. This establishes the absolute configurations of both enantiomers of exo-brevicomin and afforded key materials to clarify the relationship between pheromone activity and chirality.