GAS-CHROMATOGRAPHIC ANALYSIS OF DIASTEREOMERS AND ENANTIOMERS OF BETA,GAMMA-UNSATURATED ESTERS AND VARIOUS ANALOGS OF BUTENOLIDES INCLUDINGMINT AND ISOMINT LACTONE AND COMPARISON WITH THE HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHIC ANALYSIS OF THEIR DIASTEREOMERS
As. Tambe et al., GAS-CHROMATOGRAPHIC ANALYSIS OF DIASTEREOMERS AND ENANTIOMERS OF BETA,GAMMA-UNSATURATED ESTERS AND VARIOUS ANALOGS OF BUTENOLIDES INCLUDINGMINT AND ISOMINT LACTONE AND COMPARISON WITH THE HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHIC ANALYSIS OF THEIR DIASTEREOMERS, Journal of chromatography, 683(2), 1994, pp. 397-401
Butenolide is an alpha,beta-unsaturated lactone. The butenolide moiety
is present in numerous biologically active natural products, especial
ly insect sex hormones. A method was developed for the synthesis of bu
tenolides from beta,gamma-unsaturated esters. Separation of diastereom
ers and enantiomers of these esters and butenolides including mint and
isomint lactone and heritionin by GC is reported. The order of elutio
n of isomers of mint and isomint lactone was identified as RR, SS, SR
and RS on a Chirasil-Val-D column. This was also confirmed by injectin
g these samples on to a column with an L-configuration. The separation
of diastereomers by HPLC was also tried and the results were compared
with those obtained by GC.