Two-dimensional homonuclear and heteronuclear correlation NMR studies of diprenorphine: A prototypic 6α, 14α-endo-ethanotetrahydrothebaine
✍ Scribed by Samuel M. Mazza; Ronald H. Erickson; Paul R. Blake; John R. Lever
- Publisher
- John Wiley and Sons
- Year
- 1990
- Tongue
- English
- Weight
- 778 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0749-1581
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✦ Synopsis
Abstract
Analysis of the ^1^H–^1^H COSY, ^13^C–^1^H HETCOR and NOESY spectra of diprenorphine, a prototypic 6α, 14α‐endo‐ethanotetrahydrothebaine, yielded ^1^H NMR and ^13^C NMR assignments which should aid in spectral studies of structural congeners from this class of opioid ligands. ^13^C NMR assignments were in accord with those previously reported, with the exception of the C‐17 and C‐18 carbon resonances, which were shown to be reversed. Specific assignments for the non‐equivalent C‐20 and C‐21 methyl groups were possible through NOESY due to intramolecular hydrogen bonding between the 19‐hydroxy and the 6‐methoxy groups. The piperidyl ring presented a chair conformation, similar to that of morphine, with an equatorial N‐cyclopropylmethyl moiety.