C-13-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 (C-13-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 C-13-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.