Configurational Analysis of Thebaine, Codeine and 14β-Hydroxycodeinone N-Oxides
✍ Scribed by Gary W. Caldwell; A. Diane Gauthier; John E. Mills
- Publisher
- John Wiley and Sons
- Year
- 1996
- Tongue
- English
- Weight
- 546 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0749-1581
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✦ Synopsis
The 'H (400 MHz) and I3C (100 MHz) NMR peak assignments of thebaine derivatives [free base (l), hydrochloride (2 and 3), methiodide (4) and N-oxides (5 and 6) I, codeine N-oxide (7) and 14p-hydroxycodeinone N-oxide (8) were performed using various one-and two-dimensional techniques. The configurations of the quaternary nitrogen-substituted alkaloids were determined. The reaction of thebaine, codeine and 14~-hydroxycodeinone with H,O, produced thebaine N-oxide with the major product (6; R, 0.62) having an N-CH, axial configuration and both codeine N-oxide (7; R, 0.40) and l4p-hydroxycodeinone N-oxide (8; Rf 0.73) with the major product having an N-CH, equatorial configuration.