UNUSUAL OXIDATION REACTIONS OF 7-ALPHA-METHYLCHOLEST-5-ENE-3-BETA,7-BETA-DIOL AND 7-ALPHA-PHENYLCHOLEST-5-ENE-3-BETA,7-BETA-DIOL

Ozonation of 7 alpha-methyl(or 7 alpha-phenyl) cholest-5-ene-3 beta,7 beta-diol 3-TBDMS ether afforded the corresponding 5 beta,6 beta-epoxy derivatives. The same product was formed by MCPBA oxidation. The reac tion of 7 alpha-phenylcholest-5-ene- 3 beta,7 beta-diol with CrO3 yiel ded o-6,7-seco-7-phenylcholest-4-ene-5-carboxaldehyde. An analogous B- seco aldehyde was obtained from 7 alpha-methylcholest-5-ene-3 beta,7 b eta-diol in addition to 7-methylcholesta-4,6-dien-3-one. Jones oxidati on of 7 alpha-phenylcholest-5-ene-3 3 beta,7 beta-diol or B-seco-aldeh yde gave 3,7-dioxo-6,7-seco-7-phenylcholest-4-en-6-oic acid isolated a s its methyl ester upon treatment with diazomethane.