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

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

Source and publish data:

Tetrahedron Letters p. 5727 - 5730 (1994)

Update date:2022-08-16

Topics:

Authors:

Lopez, Dolores

Quinoa, Emilio

Riguera, Ricardo

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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.

Full text of DOI:10.1016/S0040-4039(00)77290-X

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