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Direct Synthesis of Noroxymorphone from Thebaine: Unusual Ce IV Oxidation of a Methoxydiene‐Iron Complex to an Enone‐γ‐Nitrate
Author(s) -
Machara Ales,
EndomaArias Mary Ann A.,
Císařová Ivana,
Cox D. Phillip,
Hudlicky Tomas
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600153
Subject(s) - chemistry , thebaine , ceric ammonium nitrate , moiety , enone , nitrate , ammonium nitrate , inorganic chemistry , medicinal chemistry , organic chemistry , medicine , codeine , morphine , pharmacology , grafting , polymer
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.