Abstract
Details are given for the determination by a chiral shift reagent of enantiomer compositions of several bark beetle pheromone components, which are bicyclic ketals. The procedure was carried out on three samples in the range of 200 micrograms. For one sample, the determination was achieved at the level of 5 micrograms.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Browne, L.E., Birch, M.C., andWood, D.L. 1974. Novel trapping and delivery systems for airborne insect pheromones.J. Insect Physiol. 20:183–193.
Brownlee, R.G., andSilverstein, R.M. 1968. A micro-preparative gas Chromatograph and a modified carbon skeleton determinator.Anal. Chem. 40:2077–2079.
Byrne, K.J., Gore, W.E., Pearce, G.T., andSilverstein, R.M. 1975. Porapak-Q collection of airborne organic compounds serving as models for insect pheromones.J. Chem. Ecol. 1:l-7.
Goering, H.L., Erhenberry, J.N., Koermer, G.S., andLattimer, C.J. 1974. Direct determination of enautiomeric compositions with optically active nuclear magnetic resonance lanthanide shift reagents.J. Am. Chem. Soc. 96:7842–7844.
Gore, W.E., andArmitage, I.M. 1976. Lanthanide-induced chemical shifts and the relative stereochemistry of multistriatin.J. Org. Chem. 41:1926–1930.
Gore, W.E., Pearce, G.T., andSilverstein, R.M. 1975. Relative stereochemistry of multistriatin (2,4-dimethyl-5-ethyl-6,8-dioxabicyclo[3.2.1]octane).J. Org. Chem. 40:1705–1708.
Kinzer, G.W., Fentiman, A.F., Jr., Page, T.E., Jr., Foltz, R.L., Vité, J.P., andPitman, G.B. 1969. Bark beetle attractants: Identification, synthesis and field bioassay of a new compound fromDendroctonus. Nature 221:477–478.
McCreary, M.D., Lewis, D.W., Warnick, D.L., andWhitesides, G.M. 1974. The determination of enantiomeric purity using lanthanide shift reagents.J. Am. Chem. Soc. 96:1038–1054.
Mori, K. 1974. Synthesis ofexo-brevicomin, the pheromone of western pine beetle, to obtain optically active forms of known absolute configuration.Tetrahedron 30:4223–4227.
Mori, K. 1975. Synthesis of optically active forms of frontalin, the pheromone ofDendroctonus bark beetles.Tetrahedron 31:1381–1384.
Peacock, J.W., Cuthbert, R.A., Gore, W.E., Lanier, G.N., Pearce, G.T., andSilverstein, R.M. 1975. Collection on Porapak-Q of the aggregation pheromone ofScolytus multistriatus (Coleoptera: Scolytidae).J. Chem. Ecol. 1:149–160.
Pearce, G.T., Gore, W.E., Silverstein, R.M., Peacock, J.R., Cuthbert, R.A., Lanier, G.N., andSimeone, J.B. 1975. Chemical attractants for the smaller European elm bark beetle,Scolytus multistriatus (Coleoptera: Scolytidae).J. Chem. Ecol. 1:115–124.
Pearce, G.T., Gore, W.E., andSilverstein, R.M. 1976. Synthesis and absolute configuration of multistriatin.J. Org. Chem. 41:2797–2803.
Plummer, E.L., Stewart, T.E., Byrne, K., Pearce, G.T., andSilverstein, R.M. 1976. Determinations of the enantiomeric composition of several insect pheromone alcohols.J. Chem. Ecol., 2:307–331.
Shoolery, J. 1975. Superb Spectral Quality with a 5-microgram gelsemine sample in one hour.Varian Instrum. Appl. 9:6–7.
Silverstein, R.M., andYoung, J.C. (1976). Insects generally use multicomponent pheromones,in M. Beroza (ed.), Prospects for Insect Pest Management with Sex Attractants and Other Behavior-Controlling Chemicals, American Chemical Society, Washington, D.C.
Silverstein, R.M., Brownlee, R.G., Bellas, T.E., Wood, D.L., andBrowne, L.E. 1968. Brevicomin; principal sex attractant in frass of the female western pine beetle.Science 159:889–891.
Wood, D.L., Browne, L.E., Ewing, B., Lindahl, K., Bedard, W.D., Tilden, P.E., Mori, K., Pitman, G.B., andHughes, P.R. 1976. Western pine beetle: Specificity among enantiomers of the male and female components of an attractant pheromone.Science 192:896–898.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Stewart, T.E., Plummer, E.L., McCandless, L.L. et al. Determination of enantiomer composition of several bicyclic ketal insect pheromone components. J Chem Ecol 3, 27–43 (1977). https://doi.org/10.1007/BF00988131
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/BF00988131