NMR spectra and geometry of epi N-oxides of sparteine and some of its derivatives in solution

Add time:08/22/2019    Source:sciencedirect.com

Four epi N-oxides of sparteine and its derivatives were prepared (13α-hydroxysparteine epi N-oxide (3) and 13α-hydroxylupanine N-oxide (5) for the first time) and their 1H and 13C NMR spectra were assigned using two-dimensional techniques. As sparteine (1) and 13α-hydroxysparteine (10) are conformationally homogeneous and their epi N-oxides 2 and 3 retain the same conformation (with a boat ring C), the N-oxidation effect could be determined better than before in this class of compounds. The hydroxyl group and lactam effects were also determined. The HCCH angles calculated for 2,3,4, and 5 using the generalized Karplus equation are consistent with those obtained by X-ray diffraction for two salts of 2.

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