Enantiomeric resolution of (±)-licarin A by high-performance liquid-chromatography using a chiral stationary phase

(±)-Licarin A (1), a neolignan obtained by the oxidative coupling reaction of isoeugenol, had in this study its enantiomers resolved. A novel, quick and efficient enantiomeric resolution of 1 was directly performed by chiral high-performance liquid chromatography (HPLC-PDA) protocol (CHIRALPACK® AD column; 9:1 (v/v) n-hexane:2-propanol; 1.0 mL/min). This method provided a chromatogram profile with a well-resolved peak separation. After isolation of each enantiomer with ee > 99.9%, they were analysed in a polarimeter. Compound 2, which showed a retention time (tr) of 12.13 min, was the (+)-enantiomer and compound 3 (tr = 18.90 min) was the (−)-enantiomer.