Gestodene, SH-546, SHB-331

孕二烯酮Chemical Name: 13-Ethyl-17-hydroxy-18,19-dinor-17alpha-pregna-4,15-dien-20-yn-3-one
CAS No. 60282-87-3
项目整合开发状态: Phase III
项目研究机构: Schering AG (Originator)
合成路线:18-Methyl-4-oestrene-3,17-dione (I) is hydroxylated by fermentation with Penicillium raistrickii giving the 15alpha-hydroxy compound (II),which is ketalized with 2,2-dimethylpropanediol (A),triethyl orthoformate and p-toluenesulfonic acid in CH2Cl2 giving a mixture of the DELTA(5-6) and DELTA(5-10)-ketals (IIIa-b).These ketals are mesylated witn methanesulfonyl chloride in pyridine yielding the mesyl ester (IVa-b),which is treated with sodium acetate in DMF to afford the oestradiene ketal (Va-b).Finally,this compound is treated with ethynylmagnesium bromide (B) and refluxed with oxalic acid (C) in methanol.

合成路线:Ketals (IIIa-b) can also be treated with trimethylsilyl chloride in pyridine to give the trimethylsilyl derivative (VIa-b),which is then treated with ethynylmagnesium bromide (B) and oxalic acid (C) in methanol.

合成路线:Ketals (IIIa-b) can also be acetylated with acetic anhydride in pyridine to the acetate (VIIa-b),which is then treated with ethynylmagnesium bromide (B) and oxalic acid (C) in methanol.