Application of the Ugi reaction for the one-pot synthesis of uracil polyoxin C analogues.
Andrew Plant, Peter Thompson, David M Williams
文献索引：J. Org. Chem. 74(13) , 4870-3, (2009)
全文：HTML全文
摘要
A simple, two-step synthesis of amide derivatives of uracil polyoxin C (UPOC) methyl ester using the Ugi reaction is described. The four components employed in the Ugi reaction are 2',3'-isopropylidine-protected uridine-5'-aldehyde, 2,4-dimethoxybenzylamine, an isoxazolecarboxylic acid, and the convertible isonitrile N-(2-{[(tert-butyldimethylsilyl)oxy]methyl}phenyl)carbonitrile. Following the Ugi reaction, treatment with HCl in MeOH achieves deprotection of the isopropylidene group and the N-benzyl group and conversion of the isonitrile-derived amide (the Ugi product) into the corresponding methyl ester. The procedure is amenable to automated multiparallel synthesis of novel compounds related to the polyoxin and nikkomycin nucleoside-peptide antibiotics.
相关化合物
| 结构式 | 名称/CAS号 | 分子式 | 全部文献 |
|---|---|---|---|
 |
2,4-二甲氧基苄胺
CAS:20781-20-8 |
C9H13NO2 |
|
Total synthesis of (-)-muraymycin D2 and its epimer.
2010-03-05 [J. Org. Chem. 75(5) , 1366-77, (2010)] |
|
Synthesis of N-hydroxythiourea.
1976-02-01 [J. Med. Chem. 19(2) , 336-7, (1976)] |
|
CCR5 antagonists as anti-HIV-1 agents. 1. Synthesis and biol...
2004-01-01 [Chem. Pharm. Bull. 52 , 63-73, (2004)] |
|
Polymer-supported N-derivatized, o-linked hydroxylamine for ...
2003-10-01 [J. Comb. Chem. 8(3) , 435-9, (2006)] |
|
Synthesis of 5-substituted 4-O-methyl tetramates. Jones RC a...
[Tetrahedron Lett. 27(43) , 5285-5288, (1986)] |