Novel Stereoselective Synthesis of 7β-Methyl-Substituted 5-Androstene Derivatives

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Abstract
The 7β-methyl-5-androstene derivatives 11a−c were prepared in good yield with high stereoselectivities starting from 3β-acetoxyandrost-5-en-17-one 4. The addition of methylmagnesium iodide to the 7-carbonyl group of 7a−c gave, after hydrolysis, two isomers 9a−c and 10a−c, which were stereoselectively deoxygenated by means of an ionic hydrogenation to afford the compounds 11a−c.