Abstract
tert-Butyl chromate oxidation of some steroidal 3, 5-dienes was examined. The oxidation proceeded first at C-7 and then at C-2 irrespective of what substituent was at C-3. Thus some 3, 5-diene-2, 7-diones were obtained by reoxidation of 3, 5-dien-7-one. 1, 6-Addition of methylmagnesium iodide to 17β-acetoxyandrosta-3, 5-dien-7-one afforded 17β-hydroxy-3α-methylandrost-4-en-7-one, which was converted to 17β-acetoxy-3α-methyl-androst-5-en-7-one by treatment with acetic acid and concentrated hydrochloric acid. Similarly 17β-acetoxy-3, 3-dimethylandrost-5-en-7-one was obtained from 17β-acetoxy-3-methylandrosta-3, 5-dien-7-one.
