Synthesis of pindikamine A, a michellamine-related dimer of a non-natural, 'skew' naphthylisoquinoline

被引：23

作者：

Bringmann, G ^{[1
]}

Gotz, R ^{[1
]}

Francois, G ^{[1
]}

机构：

[1] INST TROP MED PRINCE LEOPOLD,B-2000 ANTWERP,BELGIUM

来源：

TETRAHEDRON | 1996年 / 52卷 / 42期

关键词：

D O I：

10.1016/0040-4020(96)00813-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of an unnatural dimeric naphthylisoquinoline, pindikamine A (3), as a 'skew' analog of antiviral michellamines, is described. Because of the unusual coupling positions, this C-2-symmetric quateraryl is the first michellamine analog without axial chirality. Key steps of the total synthesis are the preparation of the molecular precursor 9 by intermolecular biaryl coupling, followed by a highly efficient oxidative 'dimerization' to give 8, which is transformed to 3. Pindikamine A (3) and its monomeric 'half 10 show good antimalarial activity against Plasmodium falciparum in vitro. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：13419 / 13426

页数：8

共 25 条

[1] ANTI-HIV MICHELLAMINES FROM ANCISTROCLADUS-KORUPENSIS [J].

BOYD, MR ;

HALLOCK, YF ;

MANFREDI, KP ;

BLUNT, JW ;

MCMAHON, JB ;

BUCKHEIT, RW ;

BRINGMANN, G ;

SCHAFFER, M ;

CRAGG, GM ;

THOMAS, DW ;

JATO, JG ;

CARDELLINA, JH .

JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) :1740-1745

[2]

BOYD MR, COMMUNICATION

[3] ACETOGENIC ISOQUINOLINE ALKALOIDS .16. ON THE STRUCTURE OF THE DIONCOPHYLLACEAE ALKALOIDS DIONCOPHYLLINE-A (TRIPHYOPHYLLINE) AND O-METHYL-TRIPHYOPHYLLINE [J].

BRINGMANN, G ;

RUBENACKER, M ;

JANSEN, JR ;

SCHEUTZOW, D ;

ASSI, LA .

TETRAHEDRON LETTERS, 1990, 31 (05) :639-642

[4] THE ABSOLUTE-CONFIGURATION OF MICHELLAMINE-B, A DIMERIC, ANTI-HIV-ACTIVE NAPHTHYLISOQUINOLINE ALKALOID [J].

BRINGMANN, G ;

ZAGST, R ;

SCHAFFER, M ;

HALLOCK, YF ;

CARDELLINA, JH ;

BOYD, MR .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (08) :1190-1191

[5] ACETOGENIC ISOQUINOLINE ALKALOIDS .69. BIOMIMETIC OXIDATIVE DIMERIZATION OF KORUPENSAMINE A - COMPLETION OF THE FIRST TOTAL SYNTHESIS OF MICHELLAMINE-A, MICHELLAMINE-B, AND MICHELLAMINE-C [J].

BRINGMANN, G ;

HARMSEN, S ;

HOLENZ, J ;

GEUDER, T ;

GOTZ, R ;

KELLER, PA ;

WALTER, R ;

HALLOCK, YF ;

CARDELLINA, JH ;

BOYD, MR .

TETRAHEDRON, 1994, 50 (32) :9643-9648

[6] ACETOGENIC ISOQUINOLINE ALKALOIDS .66. FIRST TOTAL SYNTHESIS OF KORUPENSAMINE-A AND KORUPENSAMINE-B [J].

BRINGMANN, G ;

GOTZ, R ;

KELLER, PA ;

WALTER, R ;

HENSCHEL, P ;

SCHAFFER, M ;

STABLEIN, M ;

KELLY, TR ;

BOYD, MR .

HETEROCYCLES, 1994, 39 (02) :503-508

[7]

BRINGMANN G, 1993, LIEBIGS ANN CHEM, P877

[8]

Bringmann G., 1995, ALKALOIDS, V46, P127

[9]

BRINGMANN G, 1996, IN PRESS LIEBIGS ANN

[10]

BRINGMANN G, 1986, ALKALOIDS, V29, P141

← 1 2 3 →