L-015

Chemical Name: 6-[1-(3-Ethoxy-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)cyclopropyl]-3-methyl-2(E),4(E)-hexadienoic acid
CAS No. 252556-01-7
项目整合开发状态: Biological Testing
项目研究机构: Ligand (Originator)
合成路线:The tetrahydronaphthalene derivative (III) was prepared by condensation of 1-bromo-2-ethoxybenzene (II) with 2,5-dichloro-2,5-dimethylhexane (I) in the presence of AlCl3.Lithium-bromine exchange in (III),followed by treatment with trimethyl borate and acid quenching,provided boronic acid (IV).This was subjected to palladium-catalyzed coupling with 3-bromo-3-buten-1-ol (V) to afford the homoallylic alcohol (VI).A Simmons-Smith reaction of (VI) with chloroiodomethane and diethylzinc furnished the cyclopropyl alcohol (VII),which was further oxidized to aldehyde (VIII) employing PCC.Horner-Emmons condensation of aldehyde (VIII) with phosphonate (IX) gave rise to the dienoate ester (X).Finally,basic hydrolysis of the ester function of (X) yielded the corresponding carboxylic acid.