title: Preparative chiral liquid chromatography for enantiomeric separation of pheromones.
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.
authors.affiliation: Department of Chemistry, Simon Fraser University, Burnaby, British Columbia V5A 1S6, Canada.
authors.forename: C I
authors.initials: CI
authors.lastname: Keeling
authors.forename: H T
authors.initials: HT
authors.lastname: Ngo
authors.forename: K D
authors.initials: KD
authors.lastname: Benusic
authors.forename: K N
authors.initials: KN
authors.lastname: Slessor
mesh_terms: 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
chemical_list: 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