A facile synthesis of 3-aryl pyroglutamic acid. Facile synthesis of baclofen and chlorpheg

被引：31

作者：

Chang, MY

Sun, PP

Chen, ST ^{[1
]}

Chang, NC

机构：

[1] Acad Sinica, Inst Biol Chem, Taipei 115, Taiwan

[2] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 28期

关键词：

glutarimides; stepwise [3+2] annulation; baclofen; chlorpheg; pyroglutamic acid;

D O I：

10.1016/S0040-4039(03)01278-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile synthesis of 3-aryl pyroglutamic acids via stepwise [3+2] annulation and desulfonated hydrolysis is reported. Base-induced coupling/cyclization reactions of alpha-sulfonylacetamide with various beta-functional groups of (Z)-2-bromoacrylates yielded three contiguous chiral centers on the polysubstituted pyroglutamates system with trans-trans orientation in a one-pot synthesis. This facile strategy was used to synthesize amino acid derivatives baclofen and chlorpheg. (C) 2003 Published by Elsevier Science Ltd.

引用

页码：5271 / 5273

页数：3

共 77 条

[61] DIRECT CHAIN ELONGATION OF N-CARBAMOYLPYROGLUTAMATE - AN EFFICIENT SYNTHESIS OF (-)-PYRROLIDINE-2,5-DICARBOXYLIC ACID [J].