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Detailed 1 H and 13 C NMR structural assignment and relative stereochemistry determination for three closely related sesquiterpene lactones
Author(s) -
Heleno Vladimir Constantino Gomes,
de Oliveira Kleber Thiago,
Lopes João Luis Callegari,
Lopes Norberto Peporine,
Ferreira Antonio Gilberto
Publication year - 2008
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.2220
Subject(s) - chemistry , sesquiterpene , stereochemistry , sesquiterpene lactone , nuclear magnetic resonance spectroscopy , coupling constant , carbon 13 nmr , nmr spectra database , two dimensional nuclear magnetic resonance spectroscopy , chemical shift , proton nmr , lactone , computational chemistry , molecular mechanics , molecule , spectral line , organic chemistry , physics , particle physics , astronomy
A complete analysis of 1 H and 13 C NMR spectra of the trypanocidal sesquiterpene lactone eremantholide C and two of its analogues is described. These structurally similar sesquiterpene lactones were submitted to 1 H NMR, 13 C { 1 H} NMR, gCOSY, gHSQC, gHMBC, J‐resolved and DPFGSE‐NOE NMR techniques. The detailed analysis of those results, correlated to some computational calculations (molecular mechanics), led to the total and unequivocal assignment of all 1 H and 13 C NMR data. The determination of all 1 H/ 1 H coupling constants and all signal multiplicities, together with the elimination of previous ambiguities were also achieved. Copyright © 2008 John Wiley & Sons, Ltd.
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