title: Enantiospecific synthesis and filed evaluation of four stereoisomers of 10,14-dimethyloctadec-1-ene, a sex pheromone component secreted by female moths of the apple leafminer.
abstract: All four stereoisomers of 10,14-dimethyloctadec-1-ene, a sex pheromone component of the apple leafminer (Lyonetia prunifoliella: Lepidoptera), were synthesized starting from (R)- and (S)-propylene oxide by applying stereospecific inversion of chiral secondary tosylates as a key step. Field evaluation showed that male moths of the Japanese population were selectively attracted by the (10S,14S)-isomer and that the activity was not inhibited by the enantiomer.
authors.affiliation: a Graduate School of Bio-Applications and Systems Engineering, Tokyo University of Agriculture and Technology , Koganei, Tokyo , Japan.
authors.forename: Tomonori
authors.initials: T
authors.lastname: Taguri
authors.forename: Katuhiko
authors.initials: K
authors.lastname: Yaginuma
authors.forename: Masanobu
authors.initials: M
authors.lastname: Yamamoto
authors.forename: Toru
authors.initials: T
authors.lastname: Fujii
authors.forename: Tetsu
authors.initials: T
authors.lastname: Ando
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D000818:Animals; D060326:Chemistry Techniques, Synthetic; D005260:Female; D007915:Lepidoptera / Q000187:drug effects* / Q000378:metabolism*; D008297:Male; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: C000595989:10,14-dimethyloctadec-1-ene; D000475:Alkenes; D012724:Sex Attractants
keywords: Lyonetiidae moth; SN2 reaction; enantioselective HPLC analysis; insect pheromone; male attractant