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17-HYDROXYLUPANINE AND 17-OXYLUPANINE
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1954
Year
Bioorganic ChemistryHeterocyclicBiochemistryAnhydronium Perchlorate17-Hydroxylupanine And 17-OxylupanineNatural SciencesOrganic ChemistryBasic StrengthStereoselective SynthesisChemistryPharmacologyDerivative (Chemistry)Synthetic ChemistryTertiary CarbinolaminesNatural Product Synthesis
Silver oxide has been shown to oxidize lupanine to 17-hydroxylupanine. This base gives an anhydronium perchlorate identical with the "dehydrolupanine (NBS)" perchlorate of Marion and Leonard. 17-Oxylupanine is described, and, from the observation that it can be reduced catalytically to oxysparteine, the stereochemistry of aphylline and oxysparteine is deduced. The basic strength of tertiary carbinolamines is discussed.