Synthesis of (R)-(-)-10-methyl-2-tridecanone, the pheromone of the southern corn rootworm.

i?)-( -)-10-Methyl-2-tridecanone, the pheromone of Diabrotica undecimpunctata howardi Barber, was synthesized from (R)-( +)-citronellyl acetate.The pheromone of the southern corn rootworm, Diabrotica undecimpunctata howardi Barber, was recently identified by Tumlinson et al. as 10-methyl-2-tridecanone 1, with a chiral center at C-10.lj2)The two enantiomers of this compound have been synthesized by Sonnet.3)Field trapping experiments in the United States indicate that males of this species respond only to the (jR)-enantiomer, thus establishing the absolute configuration of the pheromone to be R}*3) Herein we report a short synthesis of (R)-(-)-l, employing (i?)-(+)-citronellol as the chiral starting material.The use of optically pure (i?)-(+)-citronellic acid or (R)-(+)-* Pheromone Synthesis.Part LVI.