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Assignment of the 1 H and 13 C NMR spectra and conformational analysis of the pyrrolizidine alkaloid 13‐ O ‐acetyldicrotaline
Author(s) -
Rycroft David S.,
Stirling Iain R.,
Robins David J.
Publication year - 1992
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.1260301310
Subject(s) - homonuclear molecule , chemistry , pyrrolizidine , pyrrolizidine alkaloid , nmr spectra database , two dimensional nuclear magnetic resonance spectroscopy , stereochemistry , alkaloid , nuclear magnetic resonance spectroscopy , carbon 13 nmr , spectral line , molecule , organic chemistry , physics , astronomy
Abstract The 1 H and 13 C NMR spectra of the pyrrolizidine alkaloid 13‐ O ‐acetyldicrotaline were studied at 4.7 T. A full assignment of the 1 H and 13 C signals was achieved by application of a variety of NMR techniques, including homonuclear 1 H NOE difference, 2D δ H /δ H phase‐sensitive COSY and δ C /δ H direct and long‐range correlation experiments. The stereochemistry at C‐13 in dicrotaline is confirmed to be S , and the conformation of the elevenmembered macrocycle is compared with that of related pyrrolizidine alkaloids.