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13C NMR Spectral characterization of epimeric rotenone and some related tetrahydrobenzopyranofurobenzopyranones
Abidi, S.L. and Abidi, M.S., 1983, 13C NMR Spectral characterization of epimeric rotenone and some related tetrahydrobenzopyranofurobenzopyranones: Journal of Heterocyclic Chemistry, v. 20, n. 6, p.1687-1692.
Abstract
The 13C nuclear magnetic resonance (nmr) spectra of epimers of rotenone and four 12a-hydroxy-analogues were examined to determine the stereochemical effect of the B/C ring fusion involving the 6a- and 12a-carbon centers. Chemical shift differences between the epimeric carbon resonances of cis- and trans-6a,12a-compounds were notably larger than those of diastereoisomers derived from the same B/C ring junction stereochemistry. Results of the spectral analysis have been useful for the quantification of mixtures of epimers and for the measurement of rates of epimerization and oxygenation.