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NMR spectra and stereochemistry of N-acetyl and N-benzoyl derivatives of solasodine

✍ Scribed by Asmita V. Patel; Gerald Blunden; Trevor A. Crabb

Publisher
John Wiley and Sons
Year
1991
Tongue
English
Weight
432 KB
Volume
29
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

N‐Acetylation of solasodine gives only one rotameric N‐acetyl derivative compared with N‐acetyl‐3‐methylpiperidine, which exists in solution as two equally populated rotamers. The ^1^H and ^13^C NMR spectra (CDCl~3~) of O,N‐diacetyl‐ and O‐acetyl‐N‐benzoylsolasodine indicate significant deviations from F‐ring chair geometry. Opening of the F ring of these derivatives in CDCl~3~ solution at 25°C, to give the corresponding furosta‐5,20(22)‐diene derivatives, was ascertained by NMR spectroscopy.

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