Norethandrolon

Reaction of estrone methyl ether with methyl Grignard reagent followed by Birch reduction and hydrolysis of the intermediate enol ether affords the prototype orally active androgen in the 19-nor series, normethandrolone (69). ° (Note that here again the addition of the methyl group proceeded stereoselectively by approach from the least hindered side.) The preparation of the ethyl homolog starts by catalytic reduction of mestranol treatment of the intermediate, 70, under the conditions of the Birch reduction and subsequent hydrolysis of the intermediate enol ether yields norethandrolone (71). ... 

The synthesis of the homologue norethandrolone starts with catalytic reduction of the side chain unsaturation in mestranol (9-1) to the corresponding ethyl derivative... 

On the way to prepare metabolites of equine norethandrolone, a Reformatsky reaction has been applied to epiandrosterone acetate 44 in refluxing benzene the authors succeeded... 

G. Carignan and B. A. Lodge, Comparative study of the applications of gas-liquid and high-performance liquid chromatography to the analysis of norethandrolone, J. Chromatogr., 779 184 (1979). 

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