Abstract
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 byMCPBA 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.
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