An in-depth study on ring-closing metathesis of carbohydrate-derived α-alkoxyacrylates:: Efficient syntheses of DAH, KDO, and 2-deoxy-β-KDO

被引：29
|
作者：
Hekking, Koen F. W. [1 ]
Moelands, Marcel A. H. [1 ]
van Delft, Floris L. [1 ]
Rutjes, Floris P. J. T. [1 ]
机构：
[1] Radboud Univ Nijmegen, Inst Mol & Mat, NL-6525 ED Nijmegen, Netherlands
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 71卷 / 17期
关键词：
D O I：
10.1021/jo060913x
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Novel, efficient synthetic pathways to DAH, KDO, and 2-deoxy-beta-KDO are described. Ring-closing metathesis (RCM) of highly functionalized alpha-alkoxyacrylate fragments resulted in a series of synthetically versatile oxygen heterocyclic intermediates. Further functionalization of the resulting enol ether double bond and subsequent deprotection provided the natural products in high overall yields, starting from commercially available protected sugars.
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收藏
页码：6444 / 6450
页数：7
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