Direct Synthesis of Noroxymorphone from Thebaine: Unusual Ce-IV Oxidation of a Methoxydiene-Iron Complex to an Enone-gamma-Nitrate

Abstrakt

Noroxymorphone was prepared from thebaine in seven operations. The key steps involved the successive N- and O-demethylations of an iron tricarbonyl complex of thebaine followed by the unusual ceric ammonium nitrate oxidation of the methoxydiene moiety to the corresponding enone-gamma-nitrate during the decomplexation of the iron tricarbonyl functionality.

Klíčová slova

• medicinal chemistry
• opioids
• alkaloids
• iron complexes
• oxidation