Direct Synthesis of Noroxymorph­one from Thebaine: Unusual CeIV Oxidation of a Methoxydiene-Iron Complex to an Enone-γ-Nitrate

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-γ-nitrate during the decomplexation of the iron tricarbonyl functionality.