Synthesis of a 2-deoxyglucosyl analogue of medermycin

MA Brimble, TJ Brenstrum

Index: Brimble; Brenstrum Journal of the Chemical Society. Perkin Transactions 1, 2001 , # 14 p. 1624 - 1634

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Citation Number: 34

Abstract

The synthesis of a 2-deoxyglucosyl analogue 6 of the C-glycosylpyranonaphthoquinone antibiotic medermycin 1 is described. The key 3-acetyl-6-(2-deoxyglucosyl)-1, 4- naphthoquinone 7 is prepared from 6-(2-deoxyglucosyl)-1, 4-naphthoquinone 21, which in turn is available by C-glycosylation of naphthol 18 with glycosyl donor 12 using BF 3· Et 2 O in acetonitrile followed by oxidative demethylation of the derived methyl ether 20. An ...