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.

journal_name

J Chem Ecol

authors

Keeling CI,Ngo HT,Benusic KD,Slessor KN

doi

10.1023/a:1010380704106

keywords:

subject

Has Abstract

pub_date

2001-03-01 00:00:00

pages

487-97

issue

3

eissn

0098-0331

issn

1573-1561

journal_volume

27

pub_type

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