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Über ein 4,5;7,9-Bis-epoxy-hasubanan

A 4,5;7,9-bis-epoxy-hasubanan. Proof of the configuration at C-9 of hydroxy-indolinocodeine derivatives

Beweis für die Konfiguration am C-9 von 9-Hydroxy-indolinocodein-Derivaten

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

Abstract

Reaction of the enol ether1 with N-bromoacetamide in methanol gave the 7 β-bromoacetal3 which rearranged in acidic media to the 7,9-epoxide5. As an oxide bridge from C-9 to C-7 in indolinocodeinone can only be formed in the α-position, the isolation of5 is the chemical proof of the configuration at C-9.

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Authors and Affiliations

  1. Institut für Pharmazeutische Chemie, Universität Wien, Währinger Straße 10, A-1090, Wien, Österreich

    Wilhelm Fleischhacker & Alfred Klement

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  1. Wilhelm Fleischhacker
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  2. Alfred Klement
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Fleischhacker, W., Klement, A. Über ein 4,5;7,9-Bis-epoxy-hasubanan. Monatshefte für Chemie 108, 953–958 (1977). https://doi.org/10.1007/BF00898059

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  • DOI: https://doi.org/10.1007/BF00898059

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