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Ein neuer Weg zum (−)-Sinomeninon

A new synthesis of (−)-sinomeninone

  • Organische Chemie und Biochemie
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

The epimeric 7-hydroxy-neopinone-dimethylacetals1 and2, under the considerate conditions of acetal hydrolysis, are converted to 8(14)-7-oxo-thebainone (4). Similar treatment of 7-hydroxy-dihydro-codeinone-dimethylacetal (6) leads to (−)-sinomeninone (5), yield 85%.

Zusammenfassung

Die beiden epimeren 7-Hydroxy-neopinon-dimethylacetale1 und2 gehen bereits unter den milden Bedingungen der Acetalhydrolyse in Δ(4) über. In Analogie zu dieser Reaktion liefert 7-Hydroxy-dihydro-codeinon-dimethylacetal (6) bei der Behandlung mit HCl den Sinomeninon-Antipoden (5), in 85proz. Ausbeute.

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Authors and Affiliations

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

    W. Fleischhacker & H. Markut

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  1. W. Fleischhacker
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  2. H. Markut
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Herrn Prof. Dr.M. Pailer mit den besten Wünschen zum 60. Geburtstag gewidmet.

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Fleischhacker, W., Markut, H. Ein neuer Weg zum (−)-Sinomeninon. Monatshefte für Chemie 102, 643–647 (1971). https://doi.org/10.1007/BF01167242

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  • DOI: https://doi.org/10.1007/BF01167242

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