Templated scaffolds of cis- and trans-tetrahydrofuran γ-amino acids:: γ-azido-β-hydroxy-tetrahydrofuran-2-carboxylates from pentono-δ-lactones

被引：31

作者：

Sanjayan, GJ ^{[1
]}

Stewart, A ^{[1
]}

Hachisu, S ^{[1
]}

Gonzalez, R ^{[1
]}

Watterson, MP ^{[1
]}

Fleet, GWJ ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 31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)01415-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Short syntheses of enantiomeric templated scaffolds of cis- and trans-tetrahydrofuran gamma-amino acids from pentono-delta-lactones derived from arabinose and ribose are reported; an unexpectedly efficient synthesis of a templated tetrahydrofuran beta-amino acid by azide displacement of a triflate beta to an ester function proceeds with remarkably little elimination. These materials should allow evaluation of such peptidomimetics to induce predisposition towards secondary structures. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：5847 / 5851

页数：5

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