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Abstract
The methanesulfonic acid-induced rearrangement of 7-chloro-6-demethoxythebaine (10) in the presence of water or alcohols resulted in new 3-hydroxy-, or 3-alkoxy-11-hydroxy-10-methoxyaporphines (13, 14, 15, 16). O-Demethylation of the 3-methoxy derivative 14 with the methanesulfonic acid/methionine reagent-combination furnished 3,10,11-trihydroxyaporphine (18).
ACKNOWLEDGMENT
The authors thank the National Science Foundation for financial support of this work (Grants OTKA No: T029941). They also thank Dr. L. Szilágyi for recording the 1H-NMR and Dr. Z. Dinya and Dr. J. Jekö for recording the mass spectra.