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Synthesis 2016; 48(12): 1803-1813
DOI: 10.1055/s-0035-1561435
DOI: 10.1055/s-0035-1561435
feature
Synthesis of Nororipavine and Noroxymorphone via N- and O-Demethylation of Iron Tricarbonyl Complex of Thebaine
Autoren
Weitere Informationen
Publikationsverlauf
Received: 07.03 2016
Accepted: 29. März 2016
Publikationsdatum:
19. April 2016 (online)
Abstract
Thebaine was converted into its iron tricarbonyl complex, which underwent successive N- and O-demethylation with BrCN and BBr3, respectively. Decomplexation of the iron tricarbonyl moiety was accomplished with ammonium cerium(IV) nitrate (CAN) and base-catalyzed hydrolysis furnished nororipavine. When excess CAN was used the methoxydiene unit was converted into its C-14 nitrate that on hydrogenation and further hydrolysis furnished noroxymorphone. Full experimental and spectral data are provided for all key compounds.
Key words
alkaloids - iron–diene complexes - nororipavine synthesis - iron decomplexation - demethylationSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1561435.
- Supporting Information (PDF) (opens in new window)
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