Abstract
Methylation of Δ8(14)-7-oxo-thebainone-methoperchlorate (1) yields 4-O-methyl-salutaridine-methoperchlorate (2), which by action of 1n-NaOH is degradated to methine3. Acidic hydrolysis of2 at room temperature yields 7-hydroxy-4-O-methyl-7.8-dehydro-metathebainone-methoperchlorate (4 a), which by heating in 10n-HClO4 solution can be rearranged to 7-hydroxy-4-O-methyl-morphothebaine-methoperchlorate (5). The structures of the new compounds2, 3, 4 a, and5 are proved.
Zusammenfassung
Durch Methylierung von Δ8(14)-7-Oxo-thebainon-methaperchlorat (1) wird 4-O-Methyl-salutaridin-methoperchlorat (2) erhalten, das beimHofmannabbau das Methin3 liefert. Einwirkung von konz. HCl auf2 bei Raumtemp. führt zu 7-Hydroxy-4-O-methyl-7.8-dehydro-metathebainon-methoperchlorat (4 a), aus dem beim Erwärmen mit 10n-HClO4 7-Hydroxy-4-O-methyl-morphothebain-methoperchlorat (5) entsteht. Die Strukturen von2, 3, 4 a und5 werden bewiesen.
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Herrn Prof. Dr.M. Pailer zum 60. Geburtstag gewidment.
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Heinisch, G., Vieböck, F. Darstellung und Reaktionen von 4-O-Methyl-salutaridin-methoperchlorat. Monatshefte für Chemie 102, 775–780 (1971). https://doi.org/10.1007/BF01167259
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DOI: https://doi.org/10.1007/BF01167259