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

AV Patel, G Blunden, TA Crabb

Index: Patel, Asmita V.; Blunden, Gerald; Crabb, Trevor A. Magnetic Resonance in Chemistry, 1991 , vol. 29, # 8 p. 794 - 800

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Citation Number: 4

Abstract

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 ...