A straightforward approach towards thiazoles and endothiopeptides via Ugi reaction

被引：60

作者：

Kazmaier, U ^{[1
]}

Ackermann, S ^{[1
]}

机构：

[1] Univ Saarland, Inst Organ Chem, D-66123 Saarbrucken, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2005年 / 3卷 / 17期

关键词：

D O I：

10.1039/b507028g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Endothiopeptides can easily be obtained via Ugi reaction using thio acids as acid components. If isonitriles with an acetal group are applied, the endothiopeptides can directly be converted into thiazoles using TMSCl-NaI under microwave irradiation.

引用

页码：3184 / 3187

页数：4

共 63 条

[1] A THIOAMIDE SUBSTRATE OF CARBOXYPEPTIDASE-A [J].

BARTLETT, PA ;

SPEAR, KL ;

JACOBSEN, NE .

BIOCHEMISTRY, 1982, 21 (07) :1608-1611

[2] Total syntheses and re-assignment of configurations of the cyclopeptides lissoclinamide 4 and lissoclinamide 5 from Lissoclinum patella [J].

Boden, CDJ ;

Pattenden, G .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (06) :875-882

[3] CARBOXYPEPTIDASE-A CATALYZED-HYDROLYSIS OF THIOPEPTIDE AND THIONESTER ANALOGS OF SPECIFIC SUBSTRATES - AN EFFECT ON KCAT FOR PEPTIDE, BUT NOT ESTER, SUBSTRATES [J].

CAMPBELL, P ;

NASHED, NT .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (19) :5221-5226

[4] Studies of Australian ascidians .5. Virenamides A-C, new cytotoxic linear peptides from the colonial didemnid ascidian Diplosoma virens [J].

Carroll, AR ;

Feng, YJ ;

Bowden, BF ;

Coll, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (12) :4059-4061

[5] NOVEL SPONGE DERIVED AMINO-ACIDS .17. A NOVEL CHLORINATED KETIDE AMINO-ACID, HERBAMIDE-A, FROM THE MARINE SPONGE DYSIDEA-HERBACEA [J].

CLARK, WD ;

CREWS, P .

TETRAHEDRON LETTERS, 1995, 36 (08) :1185-1188

[6] STUDIES ON AMINO-ACIDS AND PEPTIDES .6. METHODS FOR INTRODUCING THIOAMIDE BONDS INTO THE PEPTIDE BACKBONE - SYNTHESIS OF THE 4 MONOTHIO ANALOGS OF LEUCINE ENKEPHALIN [J].

CLAUSEN, K ;

THORSEN, M ;

LAWESSON, SO ;

SPATOLA, AF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (04) :785-798

[7] EVIDENCE OF A PEPTIDE BACKBONE CONTRIBUTION TOWARD SELECTIVE RECEPTOR RECOGNITION FOR LEUCINE ENKEPHALIN THIOAMIDE ANALOGS [J].

CLAUSEN, K ;

SPATOLA, AF ;

LEMIEUX, C ;

SCHILLER, PW ;

LAWESSON, SO .

BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1984, 120 (01) :305-310

[8] STUDIES ON AMINO-ACIDS AND PEPTIDES .1. SYNTHESIS OF N-BENZYLOXYCARBONYLENDOTHIODIPEPTIDE ESTERS [J].

CLAUSEN, K ;

THORSEN, M ;

LAWESSON, SO .

TETRAHEDRON, 1981, 37 (21) :3635-3639

[9]

Dömling A, 2005, SYNTHESIS-STUTTGART, P662

[10]

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

← 1 2 3 4 5 6 7 →