Coriariin A

马桑鞣素AChemical Name: Bis[2,3-O-bis(3,4,5-trihydroxybenzoyl)-4,6-O-cyclic(4,4',5,5',6,6'-hexahydroxybiphenyl-2,2'-dicarbonyl)-beta-D-glucopyranos-1-yl] diester with 2,3'-epoxy-3,4,4',5,5'-pentahydroxybis(benzoic acid)
CAS No. 89871-78-3
项目整合开发状态: Biological Testing
项目研究机构: Hokuriku Univ. (Originator), Okayama University (Originator)
合成路线:The silylation of the 2-nitrobenzyl glucoside (I) with Tbdms-OTf and lutidine,with simultaneous photochemical debenzylation,gives the protected glucose (II),which is treated with trichloroacetonitrile and NaOH to yield the trichloroacetimidate (III).The esterification of the dehydrodigalloyl acid (IV) with glucose (III) in refluxing benzene affords the protected glucose diester (V),which is desilylated by means of TBAF in acetic acid to afford the tetrahydroxy compound (VI).The esterification of the hydroxyl groups of (VI) with 3,4,5-tris(benzyloxy)benzoic acid (VII) by means of DCC and DMAP provides the hexaester (VIII).

合成路线:Elimination of the acetal protecting groups of (VIII) with iodine in methanol gives the tetrahydroxy compound (IX),which is esterified with the protected trihydroxybenzoic acid (X) by means of DCC and DMAP to yield the octaester (XI).

合成路线:The desilylation of (XI) by means of TBAF in acetic acid gives the tetrahydroxy compound (XII),which is submitted to an oxidative cyclization with Pb(OAc)4 and a hydrogenolytic debenzylation with H2 over Pd/C to afford the target compound,coriarlin A.