Synthesis of macrocyclic peptide analogues of proteasome inhibitor TMC-95A

被引：43

作者：

Berthelot, A ^{[1
]}

Piguel, S ^{[1
]}

Le Dour, G ^{[1
]}

Vidal, J ^{[1
]}

机构：

[1] Univ Rennes 1, Inst Chim Rennes Synth & Electrosynth Organ, UMR 6510, F-35042 Rennes, France

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 25期

关键词：

D O I：

10.1021/jo035256c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of three constrained macrocyclic peptide analogues 1 of TMC-95A as potential proteasome inhibitors is described. The key step involves a Ni(0)-mediated macrocyclization of tripeptides 2 bearing halogenated aromatic side chains for the formation of the biaryl junction. In addition, an enantioselective preparation of L-7-bromotryptophan methyl ester 3 using a Corey-O'Donnell alkylation of the glycine benzophenone imine was achieved in good overall yield with very high ee (>85%) on a multigram scale.

引用

页码：9835 / 9838

页数：4

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