Unusual Oxidation Reactions of 7α-Methyl- And 7α-Phenylcholest-5-ene-3β,7β-diol

Article abstract of DOI:10.1007/BF00807796

Ozonation of 7α-methyl (or 7α-phenyl) cholest-5-ene-3β,7β-diol 3-TBDMS ether afforded the corresponding 5β,6β-epoxy derivatives. The same product was formed by MCPBA oxidation. The reaction of 7α-phenylcholest-5-ene-3β,7β-diol with CrO₃ yielded 3,7-dioxo-6,7-seco-7-phenylcholest-4-ene-5-carboxaldehyde. An analogous B-seco aldehyde was obtained from 7α-methylcholest-5-ene-3β,7β-diol in addition to 7-methylcholesta-4,6-dien-3-one. Jones oxidation of 7α-phenylcholest-5-ene-3β,7β-diol or B-seco-aldehyde gave 3,7-dioxo-6,7-seco-7-phenylcholest-4-en-6-oic acid isolated as its methyl ester upon treatment with diazomethane.