A simple and efficient synthesis of an Asp-Gly dipeptide mimetic

被引：8

作者：

Ndungu, JM ^{[1
]}

Gu, XY ^{[1
]}

Gross, DE ^{[1
]}

Ying, JF ^{[1
]}

Hruby, VJ ^{[1
]}

机构：

[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 16期

基金：

美国国家科学基金会;

关键词：

bicyclic dipeptide; beta-substituted aspartic acid; trifluoroacetamide; cholecystokinin;

D O I：

10.1016/j.tetlet.2004.02.117

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Alkylation of N-alpha-Boc protected aspartic acid with allyl bromide in the presence of lithium bis(trimethylsilyl)amide (LHMDS) and hexamethylphosphoramide (HMPA) afforded chiral P-allyl substituted aspartic acid in good yields. After deprotection of the N-alpha-Boc group and reprotection as a trifluoroacetamide, the terminal alkene was oxidized to an aldehyde. The aldehyde was then coupled with L-cysteine through a cascade three-bond formation process to afford aspartic acid-glycine bicyclic dipeptide mimetics. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：3245 / 3247

页数：3

共 22 条

[1] ASYMMETRIC AMINO-ACID SYNTHESIS - PREPARATION OF THE BETA-ANION DERIVED FROM ASPARTIC-ACID [J].