Collect. Czech. Chem. Commun. 1979, 44, 246-250

Reduction of some mesyloxy and tosyloxy steroids with sodium iodide and zinc dust

Pavel Kočovský and Václav Černý

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Reduction of primary and secondary steroidal alcohols via their mesylates and tosylates with sodium iodide and zinc dust in 1,2-dimethoxyethane is shown to be a mild and simple preparative method for removing the hydroxyl from polyfunctional compounds. It may be successfully applied to substances with an isolated double bond, a keto group, a α-hydroxyketo, α,α'-dihydroxyketo, or α,β-unsaturated keto grouping, an isolated tertiary hydroxyl, an epoxide ring or a nitrile group. All these functions are not affected.