First synthesis of caerulomycin B.: A new synthesis of caerulomycin C

被引：54

作者：

Mongin, F ^{[1
]}

Trécourt, F ^{[1
]}

Gervais, B ^{[1
]}

Mongin, O ^{[1
]}

Quéguiner, G ^{[1
]}

机构：

[1] IRCOF, UMR 6014, Lab Chim Organ Fine & Heterocycl, F-76131 Mont St Aignan, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 10期

关键词：

D O I：

10.1021/jo010913r

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Caerulomycins produced by Streptomyces caeruleus are bipyridinic molecules endowed with antibiotic properties. The first synthesis of caerulomycin B (1) as well as a new synthesis of caerulomycin C (2) are reported. Starting from 3-hydroxypyridine, the same methodology was used to prepare both compounds 1 and 2. Efficiently controlled reactions such as metalation to allow the synthesis of 2,6-diiodo-3,4-dialkoxypyridines, which are key intermediates, and further halogen lithium exchange and cross-coupling to reach the targets molecules 1 and 2 have been developed.

引用

页码：3272 / 3276

页数：5

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