F. Carroll, P. Abraham, K. Gaetano
1991
Citations
0
Influential Citations
10
Citations
Journal
Journal of The Chemical Society-perkin Transactions 1
Abstract
(3S)-3-Hydroxyquinidine, the major metabolite of the Cinchona alkaloid quinidine, was prepared by synthetic chemical modification or microbial oxidation of quinidine. The structure of this metabolite has been demonstrated to be (3S)-3-hydroxyquinidine by 1H and 13C NMR, IR, UV and mass spectral analysis. Previously published comparisons of the 13C NMR spectra of 3-hydroxyquinidine and model compounds were used to establish the absolute stereochemistry of the metabolite (see ref. 8). This assignment has been verified by single-crystal X-ray analysis of (3S)-3-hydroxyquinidine methanesulphonate. The gas- and solution-phase conformational preference of the metabolite derived from molecular modelling and NOE studies are compared with the conformation observed by X-ray crystallography.