Synthesis of diverse macrocyclic peptidomimetics utilizing ring-closing metathesis and solid-phase synthesis

被引:47
作者
Barret, AGM [1 ]
Hennessy, AJ
Le Vézouët, R
Procopiou, PA
Seale, PW
Stefaniak, S
Upton, RJ
White, AJP
Williams, DJ
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
[2] GlaxoSmithKline, Dept Med Chem, Stevenage SG1 2NY, Herts, England
关键词
D O I
10.1021/jo0352629
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of a range of highly functionalized peptidomimetic macrocycles has been accomplished using ring-closing metathesis and enyne tandem cross-metathesis-ring-closing metathesis reactions. This approach gives access to rigidified macrocycles modeled on the structures of cyclic peptides and designed to be biologically stable. The potential for peripheral functionalization of these templates has been demonstrated using Diels-Alder reactions, palladium(O) coupling reactions, and amide formation both in the solution phase and using polymer-supported syntheses.
引用
收藏
页码:1028 / 1037
页数:10
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