Abstract
Plants of the genus Coreopsis contain rare phenylpropanoids of the 1′-hydroxyeugenol (Eu) type. To investigate the biological activities of these compounds, 1′-hydroxyeugenol isobutyrate (Eu1) and its derivatives were synthesized. The aim was to separate racemic Eul by high-performance liquid chromatography into its enantiomers on a preparative scale, in order subsequently to synthesize the equivalent esters. To control the stereoselectivity of esterification of Eul, analytical systems investigated for Eu1Eu5 can be utilized. The best results were obtained on microcrystalline cellulose triacetate (CTA), Pirkle Convent phenylglycine and Chiracel OK columns. Racemic Eu1 could be separated on a preparative scale on CTA.
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