Alkylidenecarbene insertion at anomeric C-H bonds.: Synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and 3-deoxy-D-manno-2-octulosonic acid (KDO)

被引：49
|
作者：
Wardrop, DJ [1 ]
Zhang, WM [1 ]
机构：
[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 31期
基金：
美国国家卫生研究院;
关键词：
D O I：
10.1016/S0040-4039(02)01078-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel method for the homologation of glycals to the corresponding 3-deoxy-2-ulosonic acids, based on the [1,5]-C-H bond insertion of alkylidenecarbenes, is presented. The application of this approach is illustrated through the synthesis of 3-deoxy-D-arabino-2-heptulosonic acid (DAH) and 3-deoxy-D-manno-2-octulosonic acid (KDO). (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码：5389 / 5391
页数：3
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