【药物名称】AB-0022A
化学结构式(Chemical Structure):
参考文献No.594957
标题:Structure determination and total synthesis of a novel antibacterial substance, AB0022A, produced by a cellular slime mold
作者:Sawada, T.; Aono, M.; Asakawa, S.; Ito, A.; Awano, K.
来源:J Antibiot 2000,53(9),959
合成路线图解说明:

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.

Drug Information Express,Drug R&D,Chemical Database,Patent Search.
Copyright © 2006-2024 Drug Future. All rights reserved.Contact Us