Journal of Lipid Research, Vol 38, 780-789, Copyright © 1997 by Lipid Research, Inc.
13C-NMR and mass spectral data of steroids with a 17,17-dialkyl-18-nor- 13(14)-ene substructure
VI De Brabandere, LM Thienpont, D Stockl and AP De Leenheer
Laboratoria voor Medische Biochemie en voor Klinische Analyse, Ghent, Belgium.
We present carbon-13 nuclear magnetic resonance (13C-NMR) and mass spectral
data for several androstanes and estranes having a 17,17-
dialkyl-18-nor-13(14)-ene substructure. These compounds are formed by a
Wagner-Meerwein rearrangement of steroids bearing a tertiary 17-hydroxy
group during the derivatization reaction with heptafluorobutyric anhydride.
The 13C-NMR assignments are compared with those of natural products having
a similar substructure. The mass spectra show characteristic fragment ions
for which a fragmentation mechanism is proposed.
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