Enantioselective synthesis of some tetrahydroisoquinoline and tetrahydro-β-carboline alkaloids |
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Institution: | 1. Faculty of Chemistry, Warsaw University, Pasteura 1, 02-093 Warsaw, Poland;2. National Medicines Institute, Chełmska 30/34, 00-750 Warsaw, Poland;3. Institute of Atomic Energy, 05-400 Otwock-Świerk, Poland;4. Centre of Molecular and Macromolecular Studies, Department of Heteroorganic Chemistry, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Łódź, Poland |
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Abstract: | Four alkaloids: (R)-(+)-cryspine A 5, (R)-(+)-octahydroindolo2,3-a]quinolizidine 8, (R)-(+)-harmicine 19 and (R)-(+)-desbromoarborescidine 22 were prepared via the asymmetric transfer hydrogenation reaction of a prochiral enamine (iminium salt). The enantiomeric excesses of the isolated alkaloids were determined from their 1H NMR spectra measured in the presence of (+)-(R)-tert-butylphenylphosphinothio(seleno)ic acids as chiral solvating agents. The absolute configurations at the newly created stereogenic carbon atoms were confirmed, in all cases, by X-ray crystallography. |
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