Application of tandem Ugi reaction/ring-closing metathesis in multicomponent synthesis of unsaturated nine-membered lactams

被引：68

作者：

Banfi, L ^{[1
]}

Basso, A ^{[1
]}

Guanti, G ^{[1
]}

Riva, R ^{[1
]}

机构：

[1] Dipartimento Chim & Chim Ind, I-16146 Genoa, Italy

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 41期

关键词：

D O I：

10.1016/j.tetlet.2003.08.027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new straightforward entry into unsaturated nine-membered lactams of potential use as external reverse turn inducers was developed. It is based on an Ugi multicomponent reaction using two unsaturated substrates, followed by highly stereoselective ring-closing metathesis (RCM). The synthesis of a nine-membered secondary lactam by RCM is reported for the first time. (C) 2003 Elsevier Ltd. All rights reserved.

引用

收藏

页码：7655 / 7658

页数：4

相关论文

共 27 条

[1] Cyclic RGD peptides containing azabicycloalkane reverse-turn mimics [J].

Belvisi, L ;

Caporale, A ;

Colombo, M ;

Manzoni, L ;

Potenza, D ;

Scolastico, C ;

Castorina, M ;

Cati, M ;

Giannini, G ;

Pisano, C .

HELVETICA CHIMICA ACTA, 2002, 85 (12) :4353-4368

[2] Potent integrin antagonists from a small library of RGD-including cyclic pseudopeptides [J].

Belvisi, L ;

Bernardi, A ;

Checchia, A ;

Manzoni, L ;

Potenza, D ;

Scolastico, C ;

Castorina, M ;

Cupelli, A ;

Giannini, G ;

Carminati, P ;

Pisano, C .

ORGANIC LETTERS, 2001, 3 (07) :1001-1004

[3] AN INTERNAL COORDINATE MONTE-CARLO METHOD FOR SEARCHING CONFORMATIONAL SPACE [J].

CHANG, G ;

GUIDA, WC ;

STILL, WC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (12) :4379-4386

[4] Synthesis of an eight-membered cyclic pseudo-dipeptide using ring closing metathesis [J].

Creighton, CJ ;

Reitz, AB .

ORGANIC LETTERS, 2001, 3 (06) :893-895

[5] N-methylated cyclic RGD peptides as highly active and selective αvβ3 integrin antagonists [J].

Dechantsreiter, MA ;

Planker, E ;

Mathä, B ;

Lohof, E ;

Hölzemann, G ;

Jonczyk, A ;

Goodman, SL ;

Kessler, H .

JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (16) :3033-3040

[6] Recent advances in isocyanide-based multicomponent chemistry [J].

Dömling, A .

CURRENT OPINION IN CHEMICAL BIOLOGY, 2002, 6 (03) :306-313

[7]

Dömling A, 2000, ANGEW CHEM INT EDIT, V39, P3168, DOI 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO

[8]

2-U

[9]

EVANS PA, 1992, TETRAHEDRON LETT, V33, P6857

[10] Design, synthesis, and conformational analysis of a proposed type I β-turn mimic [J].

Fink, BE ;

Kym, PR ;

Katzenellenbogen, JA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (18) :4334-4344