The conformation and absolute configuration of the two diastereoisomeric aloins A (2a) and B (2b) were proven on the basis of shielding and deshielding effects and specific NOE (nuclear Overhauser effect) associations in 1H NMR spectroscopy. Previous 1H NMR assignments were corrected and 13C NMR spectra recorded for the first time. Taking into account analogies in CD spectra as well as in NOE effects, the absolute configuration of C-10 was suggested for the epimeric pairs of naturally occurring 1,8-dihydroxy-10-C-β-D-glucopyranosyl-9-anthrones.
Studies on aloe. Part 6. Conformation and absolute configuration of aloins A and B and related 10-C-glucosyl-9-anthrones / P. Manitto, D. Monti, G. Speranza. - In: JOURNAL OF THE CHEMICAL SOCIETY. PERKIN TRANSACTIONS. I. - ISSN 0300-922X. - 5(1990), pp. 1297-1300. [10.1039/p19900001297]
Studies on aloe. Part 6. Conformation and absolute configuration of aloins A and B and related 10-C-glucosyl-9-anthrones
P. Manitto;G. SperanzaUltimo
1990
Abstract
The conformation and absolute configuration of the two diastereoisomeric aloins A (2a) and B (2b) were proven on the basis of shielding and deshielding effects and specific NOE (nuclear Overhauser effect) associations in 1H NMR spectroscopy. Previous 1H NMR assignments were corrected and 13C NMR spectra recorded for the first time. Taking into account analogies in CD spectra as well as in NOE effects, the absolute configuration of C-10 was suggested for the epimeric pairs of naturally occurring 1,8-dihydroxy-10-C-β-D-glucopyranosyl-9-anthrones.
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