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10-Methoxy-des-Basen der Codeinonreihe, 2. Mitt.: Verhalten gegen Säure

10-methoxy-des-bases of the codeinone series, II: Reactions with acid

  • Organische Chemie und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Zusammenfassung

Saure Hydrolyse des 10-Methoxy-neopinondimethylacetalmethin-methoperchlorats (1) liefert 10-Oxo-neopinon-dihydromethin-methoperchlorat (2), das in alkal. Lösung in 10-Oxo-7,8-dehydro-metathebainon-dihydromethin-methoperchlorat (7) umgewandelt werden kann. Ein Dihydroderivat (9) des (10S)-Methoxy-codeinondimethylacetal-Δ9 (14)-methin -methoperchlorats (8 a) wird beschrieben, aus dem durch Einwirkung von 5m-Säure Neopinon-methin-methoperchlorat (10) zugänglich wird. Der Beweis für die unter2, 7, 9 und10 angeführten Strukturen wird erbracht.

Abstract

Acidic hydrolysis of 10-methoxy-neopinonedimethylacetal-methine-methoperchlorate (1) yields 10-oxo-neopinone-dihydromethine-methoperchlorate (2), which in alkaline solution rearranges to 10-oxo-7,8-dehydro-metathebainone-dihydromethine-methoperchlorate (7). A dihydro-derivative (9) of (10S)-methoxy-codeinondimethylacetal-Δ9 (14)-methine-methoperchlorats (8 a) is described, which by treatment with 5m-HClO4 yields neopinone-methine-methoperchlorate (10). The structures of the new compounds2, 7, 9, 10 are proved.

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Authors and Affiliations

  1. Pharmazeutisch-Chemischen Institut der Universität Wien, Wien, Österreich

    G. Heinisch & F. Vieböck

Authors
  1. G. Heinisch
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  2. F. Vieböck
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Additional information

Herrn Prof. Dr.O. Hromatka zum 65. Geburtstag gewidmet.

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1. Mitt.:G. Heinisch undF. Vieböck, Mh. Chem.101, 1253 (1970).

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Heinisch, G., Vieböck, F. 10-Methoxy-des-Basen der Codeinonreihe, 2. Mitt.: Verhalten gegen Säure. Monatshefte für Chemie 101, 1759–1766 (1970). https://doi.org/10.1007/BF01152090

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  • DOI: https://doi.org/10.1007/BF01152090

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