Abstract
Complete assignments of the 13 C signals of diastereomeric 4,5-epoxy-3-oxo steroids based on a combination of 1D and 2D NMR techniques are described The assignments were corroborated or corrected by calculation of the absolute isotropic 13 C NMR shieldings using the Gauge Invariant
Highlights
Steroids play different roles in living organisms from both animal and vegetal kingdoms
As a part of our ongoing program on the synthesis of potentially bioactive steroids,[8,9,10,11] we require the unambiguous NMR characterization several pairs of epimeric epoxides derived from different 4-en-3-oxo-steroids that are being employed as synthetic precursors
The Nuclear Overhauser Effect Spectroscopy (NOESY) experiment ran with the epoxide 1a showed no conclusive NOE correlation between the H-4 signal at 3.02 ppm and the signal corresponding to the 19-methyl group at 1.05 ppm
Summary
Steroids play different roles in living organisms from both animal and vegetal kingdoms. 4,5-Epoxy-3-oxo-steroids can be prepared in moderate to good yield and varying diastereoselectivity by treatment with different reagents that include peracids,[4] H2O2 in alkaline media,[5] dioxiranes[6] and more recently magnesium bis(monoperoxyphthalate) hexahydrate.[7] In spite that such compounds have been extensively employed as synthetic precursors for different polyfunctional or rearranged steroids, no complete and unambiguous assignment of the 13C NMR signals of such compounds is available. This may obey to the fact that in most of the synthetic. We report on the unambiguous 13C NMR assignments of series of epimeric 4,5-epoxy-3-oxo-steroids, assisted by X-ray diffraction and Gauge Invariant Atomic Orbitals Calculation of Absolute Isotropic Shieldings
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