Photooxidation of Thebaine. A Route to 14-Hydroxymorphinones and Hydrodibenzofuran Analogs of Methadone.

Article abstract of DOI:10.1016/S0040-4039(00)77290-X

The photooxidation of thebaine (1) produces a highly functionalized hydrodibenzofuran 2 via formation of the endoperoxide and a tert-amine radical cation.Photooxidation of the quaternary ammonium salt of thebaine 6, allows the isolation of the endoperoxide 7.Photooxidation of thebaine 1 in acidic medium (TFA), yields 14-hydroxycodeinone salt 3 via the corresponding endoperoxide.