Novel stereoselective synthesis of 7beta-methyl-substituted 5-androstene derivatives
1Institute of Materia Medica, Shanghai Institute for Biological Sciences, Chinese Academy of Sciences, 294 Taiyuan Road, Shanghai 200031, PR China.
Abstract:
The 7beta-methyl-5-androstene derivatives 11a-c were prepared in good yield with high stereoselectivities starting from 3beta-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.
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