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Acta Cryst. (2003). E59, o498-o500 [ doi:10.1107/S1600536803005646 ]
(6R,9S,13R,14S)-7,8-Didehydro-3,7-dimethoxy-17-methyl-6-phenylmorphinan-4,6-diol
C.-B. Li, W.-Q. Zhang and C. Wang
Abstract: The title compound, C25H29NO4, (II), was prepared by the reaction of (9S,13R,14S)-7,8-didehydro-3,7-dimethoxy-4-hydroxy-17-methylmorphinan-6-one, (I), with phenylmagnesium bromide. Compound (II) is a tetracyclic alkaloid with four chiral centers. The piperidine ring adopts a chair conformation, while the other two aliphatic rings are in twisted chair conformations. Compound (II) is the exclusive product, which means that, because of the steric effect, the phenyl anion stereoselectively attacks the opposite side away from the original phenyl group.
Online 21 March 2003
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