One-pot multistep Bohlmann-Rahtz heteroannulation reactions: Synthesis of dimethyl sulfomycinamate

被引：78

作者：

Bagley, MC

Chapaneri, K

Dale, JW

Xiong, X

Bower, J

机构：

[1] Cardiff Univ, Sch Chem, Cardiff CF10 3AT, S Glam, Wales

[2] Vernalis, Cambridge CB1 6GB, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 04期

关键词：

D O I：

10.1021/jo048106q

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of dimethyl sulfomycinamate, the acidic methanolysis product of the sulfomycin family of thiopeptide antibiotics, from methyl 2-oxo-4-(trimethylsilyl)but-3-ynoate is achieved in a 2,3,6-trisubstituted pyridine synthesis that proceeds with total regiocontrol in 13 steps by the Bohlmann-Rahtz heteroannulation of a 1-(oxazol-4-yl)enamine or in 12 steps and 9% yield by three-component cyclocondensation with N-[3-oxo-3-(oxazol-4-yl)propanoyl]serine and ammonia in ethanol.

引用

收藏

页码：1389 / 1399

页数：11

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