13C-NMR and mass spectral data of steroids with a 17,17-dialkyl-18-nor-13(14)-ene substructure.
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.
De Brabandere
V I
VI
Laboratoria voor Medische Biochemie en voor Klinische Analyse, Ghent, Belgium.
Thienpont
L M
LM
Stöckl
D
D
De Leenheer
A P
AP
D002247:Carbon Isotopes; D008401:Gas Chromatography-Mass Spectrometry; D009682:Magnetic Resonance Spectroscopy; D013256:Steroids / Q000737:chemistry*
D002247:Carbon Isotopes; D013256:Steroids