An alternative synthesis of 17β??hydroxy??7α??methyl??19??nor??17α??pregn??5 (10)??en??20??yn??3??one (Org OD 14)

NP Van Vliet, AIA Broess, JAM Peters…

Index: Van Vliet; Broess; Peters; et al. Recueil des Travaux Chimiques des Pays Bas, 1986 , vol. 105, # 4 p. 111 - 115

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Citation Number: 10

Abstract

Abstract The title compound (4) was prepared starting from 17β, 19-dihydroxyandrosta-4, 6- dien-3-one 17, 19-diacetate (5). Copper-catalyzed conjugate addition of methylmagnesium iodide gave, after hydrolysis, 17β, 19-dihydroxy-7α-methylandrost-4-en-3-one (8a), which was converted by oxidation and deacylation into 7α-methylestr-5 (10)-ene-3, 17-dione (11). Selective protection of the 3-keto group as the dimethyl acetal, followed by ethynylation ...