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Steroids. 1989 Sep;54(3):333-44.

Synthesis and 13C-NMR analysis of 5 alpha- and 5 beta-cholestane-3,6-dione.

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  • 1Laboratory of Organic Chemistry, Agricultural University, Wageningen, The Netherlands.


Starting from cholesterol a simple and efficient synthesis of 5 alpha-cholestane-3,6-dione and 5 beta-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.

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