An intramolecular azomethine ylide-alkene cycloaddition approach to pyrrolo[3,2-c]quinolines-synthesis of a C2-truncated martinelline model

被引:58
作者
Mahmud, H [1 ]
Lovely, CJ [1 ]
Dias, HVR [1 ]
机构
[1] Univ Texas, Dept Chem & Biochem, Arlington, TX 76019 USA
基金
美国国家科学基金会;
关键词
alkaloids; cycloaddition; azomethine ylide;
D O I
10.1016/S0040-4020(01)00315-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The hexahydropyrrolo[3,2-c]quinoline core found in the Martinella alkaloids was constructed through an intramolecular [3+2] azomethine ylide-alkene cycloaddition. Some chemical manipulations of the tricycle are reported. (C) 2001 Elsevier Science Ltd. AU rights reserved.
引用
收藏
页码:4095 / 4105
页数:11
相关论文
共 29 条
[1]  
[Anonymous], 1989, Adv. Heterocycl. Chem, DOI DOI 10.1016/S0065-2725(08)60332-3
[2]   X=Y-ZH SYSTEMS AS POTENTIAL 1,3-DIPOLES .19. INTRAMOLECULAR CYCLO-ADDITIONS OF NON-STABILIZED AZOMETHINE YLIDES GENERATED VIA THE DECARBOXYLATIVE ROUTE FROM ALPHA-AMINO-ACIDS [J].
ARDILL, H ;
GRIGG, R ;
SRIDHARAN, V ;
SURENDRAKUMAR, S .
TETRAHEDRON, 1988, 44 (15) :4953-4966
[3]   A three-component coupling protocol for the synthesis of substituted hexahydropyrrolo[3,2-c]quinolines [J].
Batey, RA ;
Simoncic, PD ;
Lin, D ;
Smyj, RP ;
Lough, AJ .
CHEMICAL COMMUNICATIONS, 1999, (07) :651-652
[4]   THE STABILIZED IMINIUM YLIDE OLEFIN [3 + 2] CYCLOADDITION REACTION - TOTAL SYNTHESIS OF SCELETIUM ALKALOID-A4 [J].
CONFALONE, PN ;
HUIE, EM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (23) :7175-7178
[5]  
Ding QZ, 1999, CURR MED CHEM, V6, P1
[6]   Cyclizations of substituted benzylidene-3-alkenylamines:: Synthesis of the tricyclic core of the martinellines [J].
Frank, KE ;
Aubé, J .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (03) :655-666
[7]   DECARBOXYLATIVE TRANSAMINATION - MECHANISM AND APPLICATIONS TO THE SYNTHESIS OF HETEROCYCLIC-COMPOUNDS [J].
GRIGG, R ;
THIANPATANAGUL, S .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (03) :180-181
[8]  
Gurjar MK, 1997, HETEROCYCLES, V45, P231
[9]   Regioselective synthesis of pyrroloquinolines - Approaches to martinelline. [J].
Hadden, M ;
Stevenson, PJ .
TETRAHEDRON LETTERS, 1999, 40 (06) :1215-1218
[10]  
Hartwig JF, 1998, ANGEW CHEM INT EDIT, V37, P2046, DOI 10.1002/(SICI)1521-3773(19980817)37:15<2046::AID-ANIE2046>3.0.CO