ISSN:
0749-1581
Keywords:
Diprenorphine
;
Morphinan
;
1H NMR
;
13C NMR
;
COSY
;
NOESY
;
HETCOR
;
6α, 14α-endo-Ethanotetrahydrothebaine
;
Chemistry
;
Analytical Chemistry and Spectroscopy
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Analysis of the 1H-1H COSY, 13C-1H HETCOR and NOESY spectra of diprenorphine, a prototypic 6α, 14α-endo-ethanotetrahydrothebaine, yielded 1H NMR and 13C NMR assignments which should aid in spectral studies of structural congeners from this class of opioid ligands. 13C 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.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/mrc.1260280804
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