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Unnaturally configured 13‐ epi steroids: full 1 H and 13 C assignments and ring C–D conformations from 1 H, 1 H vicinal couplings
Author(s) -
Fielding Lee,
Diepeveen Yolande,
Fletcher Dan,
Hamilton Niall
Publication year - 2001
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.853
Subject(s) - chemistry , ring (chemistry) , vicinal , proton , envelope (radar) , stereochemistry , crystallography , physics , nuclear physics , telecommunications , radar , organic chemistry , computer science
Six steroids with inverted stereochemistry at C‐13 (13‐ epi ) were studied. Measurement of vicinal proton–proton couplings was facilitated by a 1D TOCSY experiment, which provided efficient deconvolution of the ring D protons from other signals. A simple semi‐quantitative analysis of the ring D couplings was found to be sufficient to determine the conformation of ring D. Examples of 13α, 14β half‐chair, 17β envelope and 16β envelope conformations were found. Copyright © 2001 John Wiley & Sons, Ltd.