The Horner-Wadsworth-Emmons reaction in the synthesis of macrocyclic peptides: the Trp-His-Gly-Arg derived macrocycle of moroidin

被引：35

作者：

Harrison, JR ^{[1
]}

Moody, CJ ^{[1
]}

机构：

[1] Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 28期

基金：

英国工程与自然科学研究理事会;

关键词：

D O I：

10.1016/S0040-4039(03)01258-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Trp-His-Gly-Arg derived macrocycle 4 of moroidin 1 containing the unusual tryptophan C-2 histidine N-1 link has been synthesised in protected form. The key steps are displacement of a 2-chloroindole with a histidine derived nucleophile, a Horner-Wadsworth-Emmons reaction followed by asymmetric hydrogenation to establish the tryptophan side chain, and incorporation of the Gly-Arg dipeptide by peptide coupling. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：5189 / 5191

页数：3

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