18-VDOC

Chemical Name: 21-Hydroxy-18-vinylpregn-4-ene-3,20-dione; 11-Deoxy-18-vinylcorticosterone
项目整合开发状态: Biological Testing
项目研究机构: CNRS (Originator)
合成路线:Hydrolysis of ketal (I) with p-toluenesulfonic acid in acetone provided ketone (II).The hydroxyl group of (II) was then protected as the tetrahydropyranyl ether (III) using dihydropyran and pyridinium p-toluenesulfonate.Treatment of the methyl ketone (III) with LDA at -78 C,followed by quenching with trimethylsilyl chloride afforded the silyl enol ether (IV).Oxidation of (IV) with magnesium monoperoxyphthalate in EtOH furnished the hydroxyketone (V) along with minor amounts of the 5,6-epoxide (VI),which were separated by flash chromatography.The hydroxyketone (V) was further protected as the silyl ether (VII) using tert-butyldiphenylsilyl chloride and DMAP.Acid deprotection of the tetrahydropyranyl ether of (VII) then gave the 3-hydroxy compound (VIII),which after Oppenauer oxidation with aluminum isopropoxide in N-methylpiperidone and toluene afforded the conjugated ketone (IX).The silyl protecting group of (IX) was finally removed by treatment with methanolic HCl.