Date of Award
Master of Science
A set of 28 racemic dihydrofurocoumarins and 13 dihydrofuroflavones in which the stereogenic center is located in the furan ring have been synthesized. Currently no effective asymmetric synthesis for these classes of compounds exists, although they are produced naturally by many plant species. Their diverse medicinal properties are being investigated in several laboratories. The enantioselective separation of these compounds by three native and six derivatized cyclodextrins has been evaluated in the reversed phase mode, the polar organic mode, and normal phase mode. Overall, 20 of the 28 dihydrofurocoumarin and 9 of the 13 dihydrofuroflavone analytes were baseline resolved (Rs > 1.5) on at least one of the cyclodextrin-based chiral stationary phases. The hydroxpropyl-β-cyclodextrin (Cyclobond I RSP) is the most effective chiral stationary phase (CSP) for the enantioseparations of these compounds; baseline resolving 16 and 7 of the dihydrofurocoumarin and dihydrofuroflavone analytes respectively. The 2,3-dimethyl-β-cyclodextrin (Cyclobond I DM) also performed well, separating 18 dihydrofurocoumarin and 5 dihydrofuroflavone samples respectively. The acetyl-β-cyclodextrin (Cyclobond I AC) baseline resolved 18 of the dihydrofurocoumarin samples, however, no dihydrofuroflavones were separated on this CSP. The aromatic derivatized β-cyclodextrins are only marginally effective at separating the enantiomers of these compounds in the reversed phase mode. The native cyclodextrins showed no enantioselectivity for either class of compound in the reversed phase mode. The polar organic mode and the normal phase mode have also been evaluated with these CSPs, but no enantioseparations were observed.
Douglas David Schumacher
Schumacher, Douglas David, "Cyclodextrin-based liquid chromatographic enantiomeric separation of chiral dihydrofurocoumarins and dihydrofuroflavones, emerging classes of medicinal compounds" (2003). Retrospective Theses and Dissertations. 20031.