A novel palladium-catalyzed synthesis of β-carbolines:: application in total synthesis of naturally occurring alkaloids

被引：48

作者：

Dantale, SW ^{[1
]}

Söderberg, BCG ^{[1
]}

机构：

[1] W Virginia Univ, Dept Chem, Morgantown, WV 26506 USA

来源：

TETRAHEDRON | 2003年 / 59卷 / 29期

基金：

美国国家卫生研究院;

关键词：

palladium; catalysis; alkaloids; carboline;

D O I：

10.1016/S0040-4020(03)00824-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two naturally occurring beta-carbolines, 6-methoxy-2-methyl-1,2,3,4-tetrahydro-beta-carboline and bauerine A, have been prepared using a Stille-type coupling, followed by a palladium-phosphine catalyzed N-heteroannulation as the key steps. (C) 2003 Elsevier Science Ltd. All rights reserved.

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收藏

页码：5507 / 5514

页数：8

相关论文

共 33 条

[1] TRYPTAMINES, CARBOLINES, AND RELATED COMPOUNDS .3. 1-METHYL-TRYPTAMINES AND 1-N-DIMETHYL-TRYPTAMINES [J].

ABRAMOVITCH, RA .

JOURNAL OF THE CHEMICAL SOCIETY, 1956, (NOV) :4593-4602

[2] PALLADIUM COMPLEX-CATALYZED REDUCTIVE N-HETEROCYCLIZATION OF NITROARENES - NOVEL SYNTHESIS OF INDOLE AND 2H-INDAZOLE DERIVATIVES [J].

AKAZOME, M ;

KONDO, T ;

WATANABE, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3375-3380

[3]

ARNOLD H, 1991, ORG SYNTH, V70, P111

[4]

BURKE TR, 1992, HETEROCYCLES, V34, P757

[5] Synthesis of 4-(p-methoxyphenyl)-β-carboline, a new inhibitor of cellular calcium influx [J].

Busacca, CA ;

Dong, Y .

SYNTHETIC COMMUNICATIONS, 2000, 30 (03) :501-509

[6]

COUTTS RT, 1984, HETEROCYCLES, V22, P131

[7] DEOXYGENATION REACTIONS OF ORTHO-NITROSTYRENES WITH CARBON-MONOXIDE CATALYZED BY METAL-CARBONYLS - A NEW ROUTE TO INDOLES [J].

CROTTI, C ;

CENINI, S ;

RINDONE, B ;

TOLLARI, S ;

DEMARTIN, F .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (10) :784-786

[8]

CROTTI C, 1991, J CHEM SOC FARADAY T, P2811

[9] REMOVAL OF BENZYL-TYPE PROTECTING GROUPS FROM PEPTIDES BY CATALYTIC TRANSFER HYDROGENATION WITH FORMIC-ACID [J].

ELAMIN, B ;

ANANTHARAMAIAH, GM ;

ROYER, GP ;

MEANS, GE .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (19) :3442-3444

[10] SYNTHESIS OF 6-METHOXY-2-METHYL-1,2,3,4-TETRAHYDRO-BETA-CARBOLINE [J].

FRAHN, JL ;

ILLMAN, RJ .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1974, 27 (06) :1367-1369

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