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. Issue 5 (4th May 2014)

• Record Type: Journal Article
• Authors: Taguri, Tomonori; Yaginuma, Katuhiko; Yamamoto, Masanobu; Fujii, Toru; Ando, Tetsu
• Is Part Of: Bioscience, biotechnology, and biochemistry. Volume 78:Issue 5(2014)
• Page Start: 761
• Page End: 765
• Publication Date: 2014-05-04
• Subjects: insect pheromone -- Lyonetiidae moth -- male attractant -- SN2 reaction -- enantioselective HPLC analysis; Biotechnology -- Periodicals; Biochemistry -- Periodicals; 660.6
• DOI: 10.1080/09168451.2014.905187
• Languages: English
• ISSNs: 0916-8451

Abstract

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 (10 S, 14 S )-isomer and that the activity was not inhibited by the enantiomer.