Abstract
The configurations and conformations of bimolecular aminoacetals of benzo[ c]phenanthridine alkaloids sanguinarine and chelerythrine were investigated by NMR spectroscopy, quantum chemical calculations, and X-ray analysis. The results of the complete computational conformational analysis, the calculation of the chemical shielding of the considerably populated conformers, the determination of averaged chemical shifts and comparison with experimental NMR chemical shifts observed in solution are reported. Based on these results, the relative configurations at the stereogenic centers of two diastereomers of bis(dihydrosanguinarinyl) ether were determined. The structure of the major diastereomer of bis(dihydrosanguinarinyl) ether was confirmed by X-ray analysis and specified for the solid state.
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