Skip to main content
Log in

Semiochemicals via epoxide inversion

  • Published:
Journal of Chemical Ecology Aims and scope Submit manuscript

Abstract

A sequence of reactions is presented for inverting the configurations of both epoxide carbons in 1,2-disubstituted epoxides. As examples, (+)-disparlure was converted to its enantiomer, (−)-disparlure, andexo-endo conversion of a cyclohexene oxide was demonstrated.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Besse, P., Renard, M.F., andVeschambre, H. 1994. Chemoselective synthesis of chiral epoxides. Preparation of 4-phenyl-2,3-epoxybutane and 1-phenyl-1,2-epoxypropane.Tetrahedron Asymmetry 5:1249–1268.

    Google Scholar 

  • Bierl, B.A., Beroza, M., andCollier, C.W. 1970. Potent sex attractant of the gypsy moth: Its isolation, identification, and synthesis.Science 170:87–89.

    PubMed  Google Scholar 

  • Corey, E.J., andLink, J.O. 1992. A new process for the enantioselective synthesis of chiral α-aryloxy and α-hydroxy acids.Tetrahedron Lett. 33:3431–3434.

    Google Scholar 

  • Fleming, I. 1988. Stereocontrol in organic synthesis using silicon compounds.Pure Appl. Chem. 60:71–78.

    Google Scholar 

  • Ogliaruso, M.A., andWolfe, J.F. 1993. Synthesis of lactones and lactams, pp. 19–30,in S. Patai and Z. Rappoport (eds.). John Wiley & Sons, New York.

    Google Scholar 

  • Olah, G.A., Fung, A.P., andMeidar, D. 1981. synthetic methods and reactions; 68. Nafion-H-catalyzed hydration and methanolysis of epoxides.Synthesis 1981:280–282.

    Google Scholar 

  • Oliver, J.E., andWaters, R.M. 1995. Determining enantiomeric composition of disparlure.J. Chem. Ecol. 21:199–211.

    Google Scholar 

  • Plimmer, J.R., Schwalbe, C.P., Paszek, E.C., Bierl, B.A., Webb, R.E., Marumo, S., andIwaki, S. 1977. Contrasting effectiveness of (+) and (−) enantiomers of disparlure for trapping native populations of gypsy moth in Massachusetts.Environ. Entomol. 6:518–522.

    Google Scholar 

  • Posner, G.H., andRogers, D.Z. 1977. Organic reactions at alumina surfaces. Mild and selective opening of arene and related oxides by weak oxygen and nitrogen nucleophiles.J. Am. Chem. Soc. 99:8214–8218.

    Google Scholar 

  • Rylander, P. 1979. Catalytic Hydrogenation in Organic Synthesis. Academic Press, New York. p. 271.

    Google Scholar 

  • Sonnet, P.E., andOliver, J.E. 1976a. Olefin inversion. I. Reaction of aliphatic epoxides with triphenylphosphine dihalides.J. Org. Chem. 41:3279–3283.

    Google Scholar 

  • Sonnet, P.E., andOliver, J.E. 1976b. Olefin inversion. 2. Sodium iodide reductions of vicbromochlorides and vic-dichlorides.J. Org. Chem. 41:3284–3286.

    Google Scholar 

  • Valega, T.M., andBeroza, M. 1967. Structure-activity relationships of some attractants of the Mediterranean fruit fly.J. Econ. Entomol. 60:341–347.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Oliver, J.E., Waters, R.M. & Harrison, D.J. Semiochemicals via epoxide inversion. J Chem Ecol 22, 287–294 (1996). https://doi.org/10.1007/BF02055099

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02055099

Key Words

Navigation