AB-0022A

Chemical Name: 2,4,6-Trichloro-8-hexanoyl-3,7-dimethoxydibenzo[b,d]furan-1,9-diol
项目整合开发状态: Biological Testing
项目研究机构: Kyorin (Originator)
合成路线:The title compound was isolated from the cellular slime mold Dictyostelium purpureum K1001.A method for the total synthesis of this compound has also been reported.Oxidative dimerization of 1,3,5-trimethoxybenzene (I) to the biphenyl derivative (II) was accomplished by iodination with I2/HIO3,followed by Ullmann coupling in the presence of copper powder.Demethylation and cyclization of (II) with HI in HOAc led to the tetrahydroxy dibenzofuran (III).The 1 and 9 hydroxyl groups of (III) were then protected by formation of the cyclic silyl ether (IV).Subsequent methylation with iodomethane gave the desired dimethoxy derivative (V),which was then desilylated to (VI) by treatment with tetrabutylammonium fluoride.Esterification of (VI) with caproyl chloride (VII) in pyridine afforded (VIII).Caproate ester (VIII) was then subjected to a photo-induced Fries rearrangement producing ketone (IX).Finally,complete aromatic halogenation to furnish the title compound was carried out by means of benzyltrimethylammonium tetrachloroiodate.