Semiochemicals via epoxide inversion

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, and exo-endo conversion of a cyclohexene oxide was demonstrated

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Bibliographic Details
Published in:Journal of chemical ecology 1996-02, Vol.22 (2), p.287-294
Main Authors: Oliver, J.E. (Insect Chemical Ecology Laboratory, BARC, ARS, USDA, Beltsville, MD.), Waters, R.M, Harrison, D.J
Format: Article
Language:English
Subjects:
Animal and plant ecology
Animal, plant and microbial ecology
Animals
ATRAYENTES
ATTRACTANTS
ATTRACTIF
Autoecology
Biological and medical sciences
CHEMICAL REACTIONS PATHWAYS
COMPOSE EPOXY
COMPUESTOS EPOXY
DISPARLURE
ENANTIOMERS
EPOXY COMPOUNDS
FEROMONAS SEXUALES
Fundamental and applied biological sciences. Psychology
LYMANTRIA DISPAR
PHEROMONE SEXUELLE
Protozoa. Invertebrata
SEX PHEROMONES
SYNTHESIS
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Description
Summary: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, and exo-endo conversion of a cyclohexene oxide was demonstrated
ISSN:0098-0331
1573-1561
DOI:10.1007/BF02055099