Synthetic studies on bradykinin antagonist martinellines:: construction of a pyrrolo[3,2-c]quinoline skeleton using silicon-tether RCM reaction and allylic amination

被引：33

作者：

Hara, O

Sugimoto, K

Hamada, Y

机构：

[1] Meijo Univ, Fac Pharm, Tempaku Ku, Nagoya, Aichi 4608503, Japan

[2] Chiba Univ, Grad Sch Pharmaceut Sci, Inage Ku, Chiba 2638522, Japan

来源：

TETRAHEDRON | 2004年 / 60卷 / 42期

关键词：

pyrrolo[3,2-c]quinoline; silicon-tether ring-closing metathesis; intramolecular allylic amination; martinelline; cross-metathesis;

D O I：

10.1016/j.tet.2004.08.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The pyrrolo[3,2-c]quinoline consisting of a core structure of martinellines, the first naturally occurring heterocycle, was prepared through silicon-tether ring-closing metathesis reaction and intramolecular allylic amination as key steps. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：9381 / 9390

页数：10

相关论文

共 36 条

[1] Multi-component coupling reactions:: synthesis of a guanidine containing analog of the hexahydropyrrolo[3,2-c] quinoline alkaloid martinelline [J].

Batey, RA ;

Powell, DA .

CHEMICAL COMMUNICATIONS, 2001, (22) :2362-2363

[2] 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

[3] Recent developments in olefin cross-metathesis [J].

Connon, SJ ;

Blechert, S .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (17) :1900-1923

[4] 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

[5] SYNTHESIS OF NITROGEN-HETEROCYCLES VIA CATALYTIC RING-CLOSING METATHESIS OF DIENES [J].

FU, GC ;

GRUBBS, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (18) :7324-7325

[6] THE APPLICATION OF CATALYTIC RING-CLOSING OLEFIN METATHESIS TO THE SYNTHESIS OF UNSATURATED OXYGEN HETEROCYCLES [J].

FU, GC ;

GRUBBS, RH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5426-5427

[7] SYMMETRICAL ALKOXYSILYL ETHERS - A NEW CLASS OF ALCOHOL-PROTECTING GROUPS - PREPARATION OF TERT-BUTOXYDIPHENYLSILYL ETHERS [J].

GILLARD, JW ;

FORTIN, R ;

MORTON, HE ;

YOAKIM, C ;

QUESNELLE, CA ;

DAIGNAULT, S ;

GUINDON, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (11) :2602-2608

[8]

GRAS JL, 1981, ORG SYNTH, V60, P88

[9]

GRAS JL, 1978, TETRAHEDRON LETT, P2111

[10]

Gurjar MK, 1997, HETEROCYCLES, V45, P231

← 1 2 3 4 →