A three-component reaction between benzynes, the enolate of acetaldehyde, and unsaturated esters and dihydroisoquinolines

被引:13
作者
Kraus, George A. [1 ]
Wu, Tao [1 ]
机构
[1] Iowa State Univ, Dept Chem, Ames, IA 50011 USA
关键词
Benzyne; Benzocyclobutenone; Berbines; DIELS-ALDER CYCLOADDITIONS; ORTHO-QUINODIMETHANES; ASYMMETRIC-SYNTHESIS; O-QUINODIMETHANES; ALDEHYDES; BENZOCYCLOBUTENOXIDES; ALKALOIDS; BERBINES; CORALYNE; SALTS;
D O I
10.1016/j.tet.2009.11.083
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A three-component one-pot Coupling between benzynes, the enolate of acetaldehyde and various electrophiles led to bicyclic and tetracyclic ring systems. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:569 / 572
页数:4
相关论文
共 31 条
[1]   A powerful o-quinone dimethide strategy for intermolecular Diels-Alder cycloadditions [J].
Allen, JG ;
Hentemann, MF ;
Danishefsky, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (04) :571-575
[2]   3,6-DIMETHOXYBENZOCYCLOBUTENONE - A REAGENT FOR QUINONE SYNTHESIS [J].
AZADIARDAKANI, M ;
WALLACE, TW .
TETRAHEDRON, 1988, 44 (18) :5939-5952
[3]   AN ASYMMETRIC-SYNTHESIS OF (-)-DEOXYPODOPHYLLOTOXIN [J].
BOGUCKI, DE ;
CHARLTON, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (03) :588-593
[4]   UNSYMMETRICAL DIENOPHILES AND THEIR REACTIONS WITH ORTHO-QUINODIMETHANES [J].
CHARLTON, JL ;
BOGUCKI, D ;
GUO, P .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1995, 73 (09) :1463-1467
[5]   The asymmetric synthesis of aryltetralin lignans: (-)-isolariciresinol dimethyl ether and (-)-deoxysikkimotoxin [J].
Coltart, DM ;
Charlton, JL .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1996, 74 (01) :88-94
[6]   CONFORMATIONS, DNA BINDING PARAMETERS, AND ANTI-LEUKEMIC ACTIVITY OF CERTAIN CYTOTOXIC PROTOBERBERINE ALKALOIDS [J].
CUSHMAN, M ;
DEKOW, FW ;
JACOBSEN, LB .
JOURNAL OF MEDICINAL CHEMISTRY, 1979, 22 (03) :331-333
[7]   A CONVENIENT ONE-POT PREPARATION OF SYMMETRICAL POLYMETHOXYANTHRACENES [J].
FITZGERALD, JJ ;
DRYSDALE, NE ;
OLOFSON, RA .
SYNTHETIC COMMUNICATIONS, 1992, 22 (12) :1807-1812
[8]   REACTION OF BENZOCYCLOBUTENOXIDES WITH NITRILES - SYNTHESIS OF HYPECUMINE AND OTHER 3-SUBSTITUTED ISOQUINOLINES [J].
FITZGERALD, JJ ;
MICHAEL, FE ;
OLOFSON, RA .
TETRAHEDRON LETTERS, 1994, 35 (49) :9191-9194
[9]   REACTION OF BENZOCYCLOBUTENOXIDES WITH ALDEHYDES - SYNTHESIS OF PESHAWARINE AND OTHER 3,4-DIHYDROISOCOUMARINS [J].
FITZGERALD, JJ ;
PAGANO, AR ;
SAKODA, VM ;
OLOFSON, RA .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (15) :4117-4121
[10]   A RAPID, CONVERGENT, AND REGIOSELECTIVE SYNTHESIS OF ANTHRACENES [J].
FITZGERALD, JJ ;
DRYSDALE, NE ;
OLOFSON, RA .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7122-7126