A SHORT ENTRY INTO THE PYRIDO[2,3-B]INDOLE RING-SYSTEM - SYNTHESIS OF THE TETRACYCLIC SEGMENT OF THE MARINE ANTITUMOR AGENTS - GROSSULARINE-1 AND GROSSULARINE-2

被引：59

作者：

ACHAB, S ^{[1
]}

GUYOT, M ^{[1
]}

POTIER, P ^{[1
]}

机构：

[1] UNIV REIMS,UFR PHARM,TRANSFORMAT & SYNTH SUBSTANCES NAT LAB,CNRS,F-51096 REIMS,FRANCE

来源：

TETRAHEDRON LETTERS | 1993年 / 34卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(00)60362-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the synthesis of substituted pyrido[2,3-b]indoles (alpha-carbolines) (14, 27-31), featuring Pd-catalyzed cross coupling between pyridine and aniline derivatives and subsequent intramolecular cyclization, has been developed. This method provided a highly convergent access to the tetrayclic segment (3) of the marine antitumor agents: grossularines-1 and -2 (1,2).

引用

页码：2127 / 2130

页数：4

共 25 条

[1] THE DIRECTED SYNTHESIS OF BIARYL COMPOUNDS - MODERN CONCEPTS AND STRATEGIES [J].

BRINGMANN, G ;

WALTER, R ;

WEIRICH, R .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (09) :977-991

[2] SYNTHETIC CONNECTIONS TO THE AROMATIC DIRECTED METALATION REACTION - ITERATIVE ORTHO METALATION-CROSS COUPLING TACTICS FOR THE CONSTRUCTION OF POLYPHENYLS [J].

CHENG, W ;

SNIECKUS, V .

TETRAHEDRON LETTERS, 1987, 28 (43) :5097-5098

[3]

ECHAVARREN AM, 1991, J ORG CHEM, V56, P3497

[4] SYNTHESES OF FUNCTIONALIZED PYRIDO[2,3-B]INDOLES [J].

FORBES, IT ;

JOHNSON, CN ;

THOMPSON, M .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (02) :275-281

[5] REGIOSELECTIVE ORTHO LITHIATION OF HALOPYRIDINES [J].

GRIBBLE, GW ;

SAULNIER, MG .

TETRAHEDRON LETTERS, 1980, 21 (43) :4137-4140

[6]

HIBINO S, 1991, CHEM PHARM BULL, V39, P79

[7] BISUBSTRATE REACTION TEMPLATES - EXAMINATION OF THE CONSEQUENCES OF IDENTICAL VERSUS DIFFERENT BINDING-SITES [J].

KELLY, TR ;

BRIDGER, GJ ;

ZHAO, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (22) :8024-8034

[8]

KURIHARA T, 1980, CHEM PHARM BULL, V28, P2972

[9] SYNTHESIS OF ANNELATED NADH MODELS IN BENZOTHIENO[2,3-B]PYRIDINE AND PYRIDO[2,3-B]INDOLE SERIES [J].

LEVACHER, V ;

BOUSSAD, N ;

DUPAS, G ;

BOURGUIGNON, J ;

QUEGUINER, G .

TETRAHEDRON, 1992, 48 (05) :831-840

[10]

MALINOWSKI M, 1988, B SOC CHIM BELG, V97, P51

← 1 2 3 →