Journal of Lipid Research (Apr 1997)

13C-NMR and mass spectral data of steroids with a 17,17-dialkyl-18-nor-13(14)-ene substructure

  • V I De Brabandere,
  • L M Thienpont,
  • D Stöckl,
  • A P De Leenheer

Journal volume & issue
Vol. 38, no. 4
pp. 780 – 789

Abstract

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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.