Configurations and conformations of sanguinarine and chelerythrine free bases stereoisomers

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 calcul...

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Bibliographic Details
Published inJournal of molecular structure Vol. 613; no. 1; pp. 103 - 113
Main Authors Toušek, Jaromı́r, Dommisse, Roger, Dostál, Jiřı́, Žák, Zdirad, Pieters, Luc, Marek, Radek
Format Journal Article
LanguageEnglish
Published Elsevier B.V 01.08.2002
Subjects
Chelerythrine
NMR spectroscopy
Quantum chemical calculations
Sanguinarine
X-ray crystallography
X-ray crystallography
Sanguinarine
NMR spectroscopy
Quantum chemical calculations
Chelerythrine
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Summary: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.
ISSN:0022-2860
1872-8014
DOI:10.1016/S0022-2860(02)00138-2