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 (8 S-configuration was derived from (S)-( —)-2-methyl-l -butanol, and the (4S)- or (4R)-configuration was from (R)-( + )-citronellic acid.