Radical cyclization of N-acylcyanamides:: Total synthesis of luotonin A

被引：141

作者：

Servais, Aurore ^{[1
]}

Azzouz, Meriam ^{[1
]}

Lopes, David ^{[1
]}

Courillon, Christine ^{[1
]}

Malacria, Max ^{[1
]}

机构：

[1] Univ Paris 06, Chim Organ Lab, Inst Chim Mol, CNRS,UMR 7611,FR 2769, F-75252 Paris, France

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 04期

关键词：

alkaloids; cyanamides; cyclization; nitrogen heterocycles; radicals;

D O I：

10.1002/anie.200602940

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) As radical chain cascade precursors, N-acylcyanamides give rise to amide-iminyl radicals which, when appropriately substituted, can finally yield pyrroloquinazolines. The versatility of these new radical acceptors is illustrated by the formation of N-heterocycles with wide structural variation and by the total synthesis of luotonin A. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：576 / 579

页数：4

共 70 条

[1] Tandem radical reactions [J].

Albert, Matthias ;

Fensterbank, Louis ;

Lacote, Emmanuel ;

Malacria, Max .

RADICALS IN SYNTHESIS II: COMPLEX MOLECULES, 2006, 264 :1-62

[2] New light-induced iminyl radical cyclization reactions of acyloximes to isoquinolines [J].

Alonso, Rafael ;

Campos, Pedro J. ;

Garcia, Barbara ;

Rodriguez, Miguel A. .

ORGANIC LETTERS, 2006, 8 (16) :3521-3523

[3] REARRANGEMENT OF SUITABLY CONSTITUTED ARYL, ALKYL, OR VINYL RADICALS BY ACYL OR CYANO GROUP MIGRATION [J].

BECKWITH, ALJ ;

OSHEA, DM ;

WESTWOOD, SW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (08) :2565-2575

[4] CYANO OR ACYL GROUP MIGRATION BY CONSECUTIVE HOMOLYTIC ADDITION AND BETA-FISSION [J].

BECKWITH, ALJ ;

OSHEA, DM ;

GERBA, S ;

WESTWOOD, SW .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (09) :666-667

[5] A new radical-based route to calothrixin B [J].

Bennasar, ML ;

Roca, T ;

Ferrando, F .

ORGANIC LETTERS, 2006, 8 (04) :561-564

[6] Regioselective 6-endo cyclizations of 2-indolylacyl radicals:: Total synthesis of the pyrido[4,3-b]carbazole alkaloid guatambuine [J].

Bennasar, ML ;

Roca, T ;

Ferrando, F .

JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (04) :1746-1749

[7] Intramolecular reactions of 2-indolylacyl radicals: Access to 1,2-fused ring indole derivatives [J].

Bennasar, ML ;

Roca, T ;

Ferrando, F .

ORGANIC LETTERS, 2004, 6 (05) :759-762

[8]

Boiteau L, 1998, ANGEW CHEM INT EDIT, V37, P1128, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1128::AID-ANIE1128>3.0.CO

[9]

2-P

[10]

BOITEAU L, 1998, ANGEW CHEM, V110, P1197

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