SYNTHESIS AND 13C-NMR ANALYSIS OF 5α- AND 5β-CHOLESTANE-3,6-DIONE

Article abstract of DOI:10.1016/0039-128X(89)90007-X

Starting from cholesterol a simple and efficient synthesis of 5α-cholestane-3,6-dione and 5β-cholestane-3,6-dione is described.The 13C shielding data of C-7, C-9, and C-19 in both isomers can be used in the determination of the stereochemistry at C-5 of these compounds.The combination of 13C NMR spectroscopy and the simple synthesis of both isomers offers good opportunities for the determination of the stereochemistry at C-5 of 3,6-dioxosteroids.