Solid-phase synthesis of 5-arylhistidines via a microwave-assisted Suzuki-Miyaura cross-coupling

被引：24

作者：

Cerezo, Vanessa ^{[1
]}

Amblard, Muriel ^{[2
]}

Martinez, Jean ^{[2
]}

Verdie, Pascal ^{[2
]}

Planas, Marta ^{[1
]}

Feliu, Lidia ^{[1
]}

机构：

[1] Univ Girona, Dept Quim, LIPPSO, Girona 17071, Spain

[2] Univ Montpellier 2, Univ Montpellier 1, CNRS, Fac Pharm,IBMM,UMR 5247, F-34093 Montpellier 5, France

来源：

TETRAHEDRON | 2008年 / 64卷 / 46期

关键词：

Histidine; Arylation; Suzuki-Miyaura cross-coupling; Microwave; Biaryl peptides; Solid-phase synthesis;

D O I：

10.1016/j.tet.2008.08.077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Microwave irradiation efficiently promoted the solid-phase Suzuki-Miyaura reaction of a 5-bromohistidine with various arylboronic acids in the presence of a palladium catalyst. This methodology allowed the synthesis of peptides bearing a histidine residue substituted at position 5 of the imidazole ring with a phenyl, a substituted phenyl, a pyridyl, or a thienyl ring, as well as with the benzene ring of a tyrosine residue. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：10538 / 10545

页数：8

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