Structural studies of benzophenanthridine alkaloid free bases by NMR spectroscopy

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Authors	SEČKÁŘOVÁ Pavlína MAREK Radek DOSTÁL Jiří DOMMISSE Roger ESMANS Eddy L.
Year of publication	2002
Type	Article in Periodical
Magazine / Source	Magnetic Resonance in Chemistry
MU Faculty or unit	Faculty of Science
Citation
web	http://www3.interscience.wiley.com/cgi-bin/abstract/88512831/START
Field	Organic chemistry
Keywords	NMR; 1H NMR; 13C NMR; benzophenanthridine alkaloids; free base formation; GHMBC; GSQMBC; pseudobases
Description	The free bases of eight quaternary benzo[c]phenanthridine alkaloids were investigated by 1H and 13C NMR spectroscopy. The pseudobases (the 6-hydroxy-5,6-dihydro derivatives) were found to be the only products of the alkalization in DMSO-d6 solution. In less polar solvents the formation of the bimolecular aminoacetal structure is preferred. In biological systems, free bases of the alkaloids are assumed to adopt the pseudobase structure.
Related projects:	Biomolecular Center