Synthesis of cyclic peptides using a palladium-catalyzed enyne cycloisomerization

被引：12

作者：

Balraju, V.

Dev, R. Vasu

Reddy, D. Srinivasa

Iqbal, Javed

机构：

[1] Dr Reddys Labs Ltd, Discovery Res, Hyderabad 500049, Andhra Pradesh, India

[2] Univ Hyderabad, Sch Chem, Hyderabad 500046, Andhra Pradesh, India

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 21期

关键词：

peptidomimetics; enyne cycloisomerization; cyclic peptide; Diels-Alder reaction;

D O I：

10.1016/j.tetlet.2006.03.053

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this letter, we report a palladium-catalyzed enyne cycloisomerization of linear peptides to generate small cyclic peptides embedded with a conjugated 1,3-diene. The utility of these resulting macrocyclic dienes is demonstrated by carrying out [4+2] cycloadditions with dienophiles to generate constrained cyclic peptides with cyclic linkers. (c) 2006 Elsevier Ltd. All rights reserved.

引用

收藏

页码：3569 / 3571

页数：3

相关论文

共 33 条

[1] The behavior of 1,n-enynes in the presence of transition metals [J].

Aubert, C ;

Buisine, O ;

Malacria, M .

CHEMICAL REVIEWS, 2002, 102 (03) :813-834

[2] Synthesis of conformationally constrained cyclic peptides using an intramolecular Sonogashira coupling [J].

Balraju, V ;

Reddy, DS ;

Periasamy, M ;

Iqbal, J .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23) :9626-9628

[3] Synthesis of small cyclic peptides constrained with 3-(3-aminomethylphenyl)propionic acid linkers using free radical-mediated macrocyclization [J].

Balraju, V ;

Reddy, DS ;

Periasamy, M ;

Iqbal, J .

TETRAHEDRON LETTERS, 2005, 46 (31) :5207-5210

[4] ACCELERATION OF DIELS-ALDER REACTIONS BY REMOTE METHYL-GROUPS [J].

BARAN, J ;

MAYR, H .

TETRAHEDRON, 1989, 45 (11) :3347-3350

[5] 3,4-BISMETHYLENECYCLOPENTANONE ETHYLENE KETAL - A USEFUL DIENE FOR [6.5] RING-SYSTEMS - APPLICATION TO A FORMAL SYNTHESIS OF GIBBERELLIC-ACID [J].

BARCO, A ;

BENETTI, S ;

CASOLARI, A ;

MANFREDINI, S ;

POLLINI, GP ;

POLO, E ;

ZANIRATO, V .

TETRAHEDRON, 1989, 45 (12) :3935-3944

[6] Synthesis of diverse macrocyclic peptidomimetics utilizing ring-closing metathesis and solid-phase synthesis [J].

Barret, AGM ;

Hennessy, AJ ;

Le Vézouët, R ;

Procopiou, PA ;

Seale, PW ;

Stefaniak, S ;

Upton, RJ ;

White, AJP ;

Williams, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (04) :1028-1037

[7] The heck reaction as a sharpening stone of palladium catalysis [J].

Beletskaya, IP ;

Cheprakov, AV .

CHEMICAL REVIEWS, 2000, 100 (08) :3009-3066

[8]

ERIC CH, 2003, J AM CHEM SOC, V125, P9582

[9] Metal-catalyzed carbocyclization by intramolecular reaction of allylsilanes and allylstannanes with alkynes [J].

Fernández-Rivas, C ;

Méndez, M ;

Echavarren, AM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (06) :1221-1222

[10]

Heck R.F., 1985, PALLADIUM REAGENTS O

← 1 2 3 4 →