Preparative chiral liquid chromatography for enantiomeric separation of pheromones.
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.
Keeling
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CI
Department of Chemistry, Simon Fraser University, Burnaby, British Columbia V5A 1S6, Canada.
Ngo
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HT
Benusic
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Slessor
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KN
D000081008:Bicyclic Monoterpenes; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry / Q000302:isolation & purification; D002482:Cellulose / Q000031:analogs & derivatives* / Q000737:chemistry*; D002853:Chromatography, Liquid / Q000379:methods*; D010675:Pheromones / Q000737:chemistry / Q000302:isolation & purification*; D011714:Pyrans; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry / Q000302:isolation & purification
D000081008:Bicyclic Monoterpenes; D019086:Bridged Bicyclo Compounds, Heterocyclic; D010675:Pheromones; D011714:Pyrans; D013729:Terpenes; C037523:lineatin; D002482:Cellulose; C024671:cellulose triacetate; C052875:verbenone; C013009:grandisol; C012327:frontalin; C012219:brevicomin