合成路线:The oxidation of PGF2alpha with 2,3-dichloro-5,6-dicyanobenzoquinone gives 15-keto-PGF2alpha (I),which is silylated as usual with TMSCl to the tris-trimethylsilyl derivative (II).The normal methylation of (II) with methylmagnesium bromide followed by hydrolysis yields the 15-methyl PGF2alpha (IIIa-b),which is then methylated with diazomethane to the 15-methyl PGF2alpha methyl ester (IV).The selective silylation of 15-methyl PGF2alpha methyl ester (IV) at C-11 with an excess of trimethylsilyldiethylamine (A) in acetone at -45 C gives the monotrimethylsilyl derivative (V),m.p.33-5 C,which is oxidized with CrO3-dipyridine in pyridine to the ketone (VI) and finally hydrolyzed with aqueous methanol and a small amount of acetic acid to the 15-methyl PGE2 methyl ester.
参考文献标题:Novel prostaglandin syntheses
文献作者:Bundy,G.; et al.
参考来源:Ann NY Acad Sci 1971,18076
合成路线:The oxidation of PGF2alpha with 2,3-dichloro-5,6-dicyanobenzoquinone gives 15-keto-PGF2alpha (I),which is silylated as usual with TMSCl to the tris-trimethylsilyl derivative (II).The normal methylation of (II) with methylmagnesium bromide followed by hydrolysis yields the 15-methyl PGF2alpha (IIIa-b),which is then methylated with diazomethane to the 15-methyl PGF2alpha methyl ester (IV).The selective silylation of 15-methyl PGF2alpha methyl ester (IV) at C-11 with an excess of trimethylsilyldiethylamine (A) in acetone at -45 C gives the monotrimethylsilyl derivative (V),m.p.33-5 C,which is oxidized with CrO3-dipyridine in pyridine to the ketone (VI) and finally hydrolyzed with aqueous methanol and a small amount of acetic acid to the 15-methyl PGE2 methyl ester.
参考文献标题:(15S)-15-Methylprostaglandin
文献作者:Bundy,G.L.; Yankee,E.W.
参考来源:J Am Chem Soc 1972,94(10),3651
产品链接: CAS No. 55028-70-1››