title: Improved synthesis and deployment of (2S,3R)-2-(2Z,5Z-octadienyl)-3-nonyloxirane, a pheromone of the pink moth, Lymantria mathura.
abstract: We report two new syntheses of (2S,3R)-2-(2Z,5Z-octadienyl)-3-nonyloxirane, the main sex pheromone component of the pink moth, Lymantria mathura. The key step in the first route was the construction of (Z,Z)-1-bromo-1,4-heptadiene (6), which was coupled in the final step with 2-iodomethyl-3-nonyloxirane 4 via a Grignard reaction. The second approach employed alkylation of 1,4-heptadiynyllithium with epoxy triflates 7 in ether/hexane and provided the pheromone in >/=37% overall yield from alcohol 2. The 4:1 ratio of pheromone enantiomers, reportedly the most attractive to pink moth males, can be directly crafted from appropriately selected Sharpless asymmetric epoxidation conditions.
authors.affiliation: Chemicals Affecting Insect Behavior Laboratory, BARC-West, PSI, ARS, USDA, Beltsville, Maryland 20705, USA. khrimiaa@ba.ars.usda.gov
authors.forename: Ashot
authors.initials: A
authors.lastname: Khrimian
authors.forename: James E
authors.initials: JE
authors.lastname: Oliver
authors.forename: Roger C
authors.initials: RC
authors.lastname: Hahn
authors.forename: Nikki H
authors.initials: NH
authors.lastname: Dees
authors.forename: Jeff
authors.initials: J
authors.lastname: White
authors.forename: Victor C
authors.initials: VC
authors.lastname: Mastro
mesh_terms: D000818:Animals; D005027:Ethylene Oxide / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D005227:Fatty Acids / Q000138:chemical synthesis* / Q000737:chemistry; D007300:Insect Control / Q000379:methods; D008297:Male; D009036:Moths / Q000502:physiology*; D010675:Pheromones; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C487532:(2S,3R)-2-(2Z,5Z-octadienyl)-3-nonyloxirane; D005227:Fatty Acids; D010675:Pheromones; D012724:Sex Attractants; C010411:insect attractants; D005027:Ethylene Oxide