Synthesis of mimosamycin

Mimosamycin (1) was synthesized in eight steps with an overall yield of 13% from 2-methoxy-3-methyl-1,4-benzoquinone by regioselective introduction of a chloromethyl group at C-6 and a methoxycarbonylmethyl group at C-5 and s ubsequent reaction of the intermediate methyl (o-(chloromethyl)phenyl)aceta te derivative 16 with methylamine, Oxidation of the 5,7,8-trimethoxy-2,6-di methyl-1,4-dihydroisoquinoline-3(2H)-one 17 thus obtained, using cerium(IV) ammonium nitrate as a selective oxidizing agent, gave mimosamycin (1) in g ood overall yield.