Synthesis of a C-glycosylpyranonaphthoquinone related to medermycin

被引：13

作者：

Brimble, MA ^{[1
]}

Brenstrum, TJ ^{[1
]}

机构：

[1] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 16期

基金：

澳大利亚研究理事会;

关键词：

C-glycosides; naphthols; 2-trimethylsilyloxyfuran; pyranonaphthoquinones;

D O I：

10.1016/S0040-4039(00)00289-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a 2-deoxyglucosyl analogue 2 of the pyranonaphthoquinone antibiotic medermycin 1 is reported. The critical beta C-glycoside linkage was introduced at an early stage in the synthesis by direct C-glycosylation of naphthol 7 with benzyl protected glycosyl donor 4. Conversion of C-glycoside 8 to 2-acetyl-1,4-naphthoquinone 3 then allowed assembly of the pyranonaphthoquinone skeleton via a furofuran annulation-oxidative rearrangement strategy. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：2991 / 2994

页数：4

共 16 条

[1] SYNTHETIC APPROACHES TO THE ANGUCYCLINE ANTIBIOTICS - SYNTHESIS OF THE C-GLYCOSIDIC CD RING-SYSTEM [J].