Efficient preparation of a 1,3-diazidocyclitol as a versatile 2-deoxystreptamine precursor

被引：24

作者：

Busscher, GF ^{[1
]}

Groothuys, S ^{[1
]}

de Gelder, R ^{[1
]}

Rutjes, FPJT ^{[1
]}

van Delft, FL ^{[1
]}

机构：

[1] Univ Nijmegen, Dept Organ & Inorgan Chem, NSRIM, NL-6525 ED Nijmegen, Netherlands

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 13期

关键词：

D O I：

10.1021/jo049788k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis route toward 2-deoxystreptamine, a common structure in many of the clinically important aminoglycosides, is presented. Starting from p-benzoquinone and cyclopentadiene, 2-deoxystreptamine is synthesized with key steps involving Pd(0)-catalyzed rearrangement, a retro-Diels-Alder by flash vacuum thermolysis, and Yb(III)-directed regioselective epoxide opening. The obtained diazidocyclitol 17 is a suitable 2-deoxystreptamine precursor, conveniently protected for incorporation in new aminoglycoside entities.

引用

页码：4477 / 4481

页数：5

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