Journal of the Chemical Society Perkin Transactions 1 · 1975 · 26 citations · 0 references
PharmacyChemistryMedicinal ChemistryDrug DiscoveryOrganic ChemistrySynthetic Medicinal ChemistryAlkaloid BiosynthesisAromatic PlantsHeterocyclic ChemistryMedicinal PlantsNatural Product Drug DiscoveryTerpenoid BiosynthesisAbsolute Configuration AssignmentAbsolute Configuration DeterminationAlkaloid GlycosidesGlycopyranose StereochemistryGlycoside SynthesisMarine AlkaloidsPlant AlkaloidsTerpenoid Glycosides
The structure and absolute configuration of O-methylalangiside (15){11-(β-D-glycopyranosyloxy)-5,11,12,12a,13,13a-hexahydro-2,3-dimethoxy-12-vinyl-6H-benzo[a]pyrano[3,4-g]quinolizin-8-one} has been established by chemical and spectroscopic studies and by correlation with ipecoside. Synthetic evidence is presented which indirectly confirms the 3-methoxy-(11) rather than the 2-methoxy-structure (12) for alangiside.