Canadian Forest Service Publications
Synthesis of chiral alkenyl epoxides: the sex pheromone of the elm spanworm Ennomous subsignaria(Hubner) Lipidoptera: Geometridae). 2011. MaGee, D.I.; Silk, P.J.; Wu, J.; Mayo, P.D.; Ryall, K. Tetrahedron 67:5329-5338.
Year: 2011
Issued by: Great Lakes Forestry Centre
Catalog ID: 32893
Language: English
Availability: PDF (request by e-mail)
Available from the Journal's Web site. †
DOI: 10.1016/j.tet.2011.05.015
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Abstract
The identification of the sex pheromone of the elm spanworm Ennomos subsignaria (Hiibner), as the chiral alkenyl epoxide (6Z)-ris-9,10-epoxy-nonadecene has been accomplished. Both enantiomers of (6Z)-cis-9,10-epoxy-nonadecene have been synthesized via two routes. The key steps in the first route were to prepare both rhreo-epoxy tosylates and then to perform an alkylative rearrangement of these intermediates to obtain the target molecules. An alternative enantioenriched synthesis that took advantage of the Sharpless dihydroxylation reaction was developed so that a common starting material could be used to accessboth enantiomers.Afield study and GC/EAD testing indicated that Z6-cis-9S,10Repoxy-nonadecene was the sex pheromoneof the elm spanworm£ subsignaria (Hiibner).