【药物名称】Arbaprostil, CU-83, U-42842, Arbastyl, Arbacet
化学结构式(Chemical Structure):
参考文献No.71681
标题:15-Methyl Prostaglandins E2
作者:Hillier, K.
来源:Drugs Fut 1976,1(9),442
合成路线图解说明:

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No.604458
标题:Novel prostaglandin syntheses
作者:Bundy, G.; et al.
来源:Ann NY Acad Sci 1971,18076
合成路线图解说明:

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No.800731
标题:(15S)-15-Methylprostaglandin
作者:Bundy, G.L.; Yankee, E.W.
来源:J Am Chem Soc 1972,94(10),3651
合成路线图解说明:

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.

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