Synthesis of Optically Active Aggregation Pheromone Analogues of the Red Flour Beetle, Tribolium castaneum

Abstract

Seven optically active analogues which were (4S)-, (8S)- and (4R)-analogues of the aggregation pheromone of the red flour beetle, Tribolium castaneum, were stereoselectively synthesized from optically pure (R)-(+)-citronellic acid (100% e.e.) and/or (S)-(-)-2-methyl-l-butanol (93% e.e.) to elucidate the structure-activity relationship of the pheromone. The (8S)-configuration was derived from (S)-(-)-2-methyl-1-butanol, and the (4S)- or (4R)-configuration was from (R)-(+)-citronellic acid.