ABSTRACT
Isopulegol, a pool of abundant chiral terpene, has long served as the starting material for the total synthesis of isopulegol-based drugs. As an inexpensive and versatile starting material, this compound continues to serve modern synthetic chemistry. This review highlights the total syntheses of terpenoids in the period from 1980 to 2020 in which with isopulegol applied as a building block.
Subject(s)
Terpenes , Cyclohexane Monoterpenes , StereoisomerismABSTRACT
Enantioseparation of limonene-based bicyclic 1,3-aminoalcohols and 1,3,5- and 1,3,6-aminodiols was performed by normal-phase high-performance liquid chromatographic and supercritical fluid chromatographic (SFC) methods on polysaccharide-based chiral stationary phases. The effects of the composition of the mobile phase, the column temperature and the structures of the analytes and chiral selectors on retention and selectivity were investigated by normal-phase LC and SFC technique. Thermodynamic parameters derived from selectivity-temperature-dependence studies were found to be dependent on the chromatographic method applied, the nature of the chiral selector and the structural details of the analytes. Enantiorecognition in most cases was enthalpically driven but an unusual temperature behavior was also observed: decreased retention times were accompanied by improved separation factors with increasing temperature, i.e. some entropically driven separations were also observed. The elution sequence was determined in all cases. The separation of the stereoisomers was optimized in both chromatographic modalities.
