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J Agric Food Chem

Title:		"Improved synthesis and deployment of (2S,3R)-2-(2Z,5Z-octadienyl)-3-nonyloxirane, a pheromone of the pink moth, Lymantria mathura"
Author(s):		Khrimian A; Oliver JE; Hahn RC; Dees NH; White J; Mastro VC;
Address:		"Chemicals Affecting Insect Behavior Laboratory, BARC-West, PSI, ARS, USDA, Beltsville, Maryland 20705, USA. khrimiaa@ba.ars.usda.gov"
Journal Title:		J Agric Food Chem
Year:		2004
Volume:		52
Issue:		10
Page Number:		2890 - 2895
DOI:		10.1021/jf035506q
ISSN/ISBN:		0021-8561 (Print) 0021-8561 (Linking)
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"
Keywords:		Animals Ethylene Oxide/analogs & derivatives/*chemical synthesis/chemistry Fatty Acids/*chemical synthesis/chemistry Insect Control/methods Male Moths/*physiology *Pheromones Sex Attractants/*chemical synthesis/chemistry Stereoisomerism Structure-Activity;
Notes:		"MedlineKhrimian, Ashot Oliver, James E Hahn, Roger C Dees, Nikki H White, Jeff Mastro, Victor C eng 2004/05/13 J Agric Food Chem. 2004 May 19; 52(10):2890-5. doi: 10.1021/jf035506q"