ANALYTIC AND PREPARATIVE RESOLUTION OF RACEMIC GAMMA-LACTONES AND DELTA-LACTONES BY CHROMATOGRAPHY ON CELLULOSE TRIACETATE - RELATIONSHIP BETWEEN ELUTION ORDER AND ABSOLUTE-CONFIGURATION

Enantiomers of various chiral five- and six-membered-ring lactones, which are important classes of compounds (flavour and pheromone components, key intermediates in the synthesis of biologically active substances) have been separated chromatographically on the chiral phase cellulose triacetate, crystallographic form 1 (CTA I). For different series of five-membered-ring lactones, relationships have been found between the elution order of the enantiomers and their absolute configurations. Preparative resolutions of .gamma.-phenyl-.gamma.-butyrolactone (1) and of the pheromone component 5b have been carried out to demonstrate the applicability of the method to g-scale separations.