Formal synthesis of (+)3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) via desymmetrization by ring-closing metathesis

被引：56

作者：

Burke, SD ^{[1
]}

Voight, EA ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 02期

关键词：

D O I：

10.1021/ol006887l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Formal synthesis of the naturally occurring deaminated sialic acid KDN, a potential oncofetal antigen, has been accomplished in 45% overall yield via a novel ketalization/ring-closing metathesis sequence, The rapid introduction of all oxygen functionality in a completely stereocontrolled manner exploited a rigid 6,8-dioxabicyclo[3.2.1]oct-2-ene ring system. This general synthetic strategy should provide access to a number of KDN and sialic acid analogues.

引用

页码：237 / 240

页数：4

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