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 subsequent reaction of the intermediate methyl (o-(chloromethyl)phenyl)acetate derivative 16 with methylamine. Oxidation of the 5,7,8-trimethoxy-2,6-dimethyl-1, 4-dihydroisoquinoline-3(2H)-one 17 thus obtained, using cerium(IV) ammonium nitrate as a selective oxidizing agent, gave mimosamycin (1) in good overall yield.
Kesteleyn
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B
Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, University of Gent, Coupure Links 653, B-9000 Gent, Belgium.
De Kimpe
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N
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
D000900:Anti-Bacterial Agents; D007546:Isoquinolines; C018106:mimosamycin