The reaction of cholesterol with ozone and alcohols: a revised mechanism and structure of the principal product

Abstract

The structure of the product formed in the course of the reaction of cholesterol acetate with ozone in alcohol-containing solvents has been revised. In methanol–chloroform, it is shown to be the hydroperoxide, 3β-acetoxy-5α-hydroperoxy-7β-methoxy-5α-B-homo-6-oxacholestane (8a), and not the previously claimed cyclic hemiperacetal, 3β-acetoxy-5-hydroxy-7a-methoxy-B-dihomo-6,7-dioxacholestane (1; R¹= AC, R²= Me).