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Two‐dimensional homonuclear and heteronuclear correlation NMR studies of diprenorphine: A prototypic 6α, 14α‐ endo ‐ethanotetrahydrothebaine
Author(s) -
Mazza Samuel M.,
Erickson Ronald H.,
Blake Paul R.,
Lever John R.
Publication year - 1990
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260280804
Subject(s) - chemistry , heteronuclear molecule , homonuclear molecule , two dimensional nuclear magnetic resonance spectroscopy , stereochemistry , intramolecular force , moiety , carbon 13 nmr , dept , nuclear magnetic resonance spectroscopy , nuclear magnetic resonance , molecule , organic chemistry , physics
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.