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 (R) 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 (t(r)) of 12.13 min, was the (+)-enantiomer and compound 3 (t(r) =18.90 min) was the (-)-enantiomer. (C) 2011 Elsevier B.V. All rights reserved.

Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP)[06/06267-5]

Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP)[1998/14956-7]

Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP)[2009/15207-4]

Fundacao de Amparo a Pesquisa do Estado de Sao Paulo (FAPESP)[2009/05049-2]

Coordenadoria de Aperfeicoamento de Pessoal do Ensino Superior (CAPES)

Conselho Nacional de Desenvolvimento Cientifico e Tecnologico (CNPq)