ST-1926

Chemical Name: 3-[3'-(1-Adamantyl)-4'-hydroxybiphenyl-4-yl]-2(E)-propenoic acid
项目整合开发状态: Preclinical
项目研究机构: Sigma-Tau (Originator)
合成路线:Friedel-Crafts condensation of 4'-bromobiphenyl-4-ol (I) with 1-adamantanol (II) affords the adamantanylbiphenyl derivative (III).This is then subjected to Heck coupling with methyl acrylate (IV) to produce the biphenylyl acrylate (V).Finally,basic hydrolysis of ester (V) leads to the title carboxylic acid.

合成路线:In an alternative method,4-(t-butyldimethylsilyloxy)-3-(1-adamantyl)bromobenzene (I) undergoes Suzuki coupling with 4-formylbenzeneboronic acid (II) to provide the biphenyl aldehyde (III).Subsequent Wittig condensation of (III) with methyl triphenylphosphoranylideneacetate (IV) yields the unsaturated ester (V).This is finally hydrolyzed with LiOH to furnish the title compound.