Asymmetric synthesis of the sex pheromone of the apple leafminer, Lyonetia prunifoliella

Abstract

Lyonetia prunifoliella is a significant pest in orchards and damages apple. The sex pheromones of this pest were prepared via a new and concise method. The central to our method were Evans' chiral auxiliaries, the addition of chiral Grignard reagent to aldehyde and Wittig coupling.

Enantioselective Synthesis of the Active Sex Pheromone Components of the Female Lichen Moth, Lyclene dharma dharma, and Their Enantiomers

“…Reductive cleavage of the chiral auxiliary with lithium aluminum hydride (LiAH 4 ) afforded ( R )-2-methylundec-10-en-1-ol (( R )- 7 ) in 88% yield and 99% ee [ 14 ]. The enantiomeric excess of ( R )- 7 was estimated by 1 H NMR spectra of its corresponding Mosher ester derivative [ 15 ]. The specific rotation of ( R )- 7 was +12.3 (c 1.17, CHCl 3 ), which matched the reported value in the literature of +8.4 (c 4.6, CHCl 3 ), which also supported that the newly constructed chiral methyl configuration is the R configuration [ 16 ].…”