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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

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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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Correspondence to Doz. Dr. Wilhelm Fleischhacker.

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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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