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J Chem Ecol ; 27(3): 487-97, 2001 Mar.
Article in English | MEDLINE | ID: mdl-11441440

ABSTRACT

Cellulose triacetate was investigated as a chiral stationary phase for preparatively separating the enantiomers of lineatin, frontalin, exo-brevicomin, endo-brevicomin, verbenone, (E)-conophthorin, and grandisol. Tens of milligrams of both enantiomers were efficiently prepared in high percentage enantiomeric excess from one injection of each compound except grandisol. We prepared grandisyl acetate, benzoate, and 4-bromobenzoate to determine if derivatization of the free alcohol might improve separation. Of these, grandisyl 4-bromobenzoate provided the best separation but was still not very well resolved. Preparative separation of enantiomers on cellulose triacetate is a viable alternative to stereoselective synthesis when semiochemicals of very high enantiomeric purity are required for biological testing.


Subject(s)
Cellulose/analogs & derivatives , Cellulose/chemistry , Chromatography, Liquid/methods , Pheromones/isolation & purification , Pyrans , Bicyclic Monoterpenes , Bridged Bicyclo Compounds, Heterocyclic/chemistry , Bridged Bicyclo Compounds, Heterocyclic/isolation & purification , Pheromones/chemistry , Stereoisomerism , Terpenes/chemistry , Terpenes/isolation & purification
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