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

Authors:
  • ZPZdzisław Paryzek
    Zdzisław Paryzek
  • JMJacek Martynow
    Jacek Martynow
  • WSWitold Swoboda
    Witold Swoboda

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).

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