New syntheses of orelline and analogues via metalation and cross-coupling reactions

被引:20
作者
Mongin, F [1 ]
Trécourt, F [1 ]
Mongin, O [1 ]
Quéguiner, G [1 ]
机构
[1] IRCOF, UMR 6014, Lab Chim Organ Fine & Heterocycl, F-76131 Mont St Aignan, France
关键词
alkaloids; pyridine; metalation; coupling reactions;
D O I
10.1016/S0040-4020(01)01142-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
New total syntheses of orelline and some analogues are reported. The methodology involves metalation of 3-alkoxy-2-iodopyridines to afford 3,4-dialkoxy-2-iodopyridines, on which cross-coupling reactions are performed to reach the 2,2'-bipyridine skeleton of the alkaloid. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:309 / 314
页数:6
相关论文
共 30 条
[1]  
[Anonymous], 1972, Inorg. Synth, DOI DOI 10.1002/9780470132449.CH23
[2]  
ANTKOWIAK WZ, 1994, HETEROCYCLES, V39, P477
[3]   PHOTODECOMPOSITION OF ORELLANINE AND ORELLININE, THE FUNGAL TOXINS OF CORTINARIUS-ORELLANUS FRIES AND CORTINARIUS-SPECIOSSIMUS [J].
ANTKOWIAK, WZ ;
GESSNER, WP .
EXPERIENTIA, 1985, 41 (06) :769-771
[4]  
ANTKOWIAK WZ, 1985, STUD ORG CHEM AMSTER, V20, P75
[5]  
ANTKOWIAK WZ, 1979, TETRAHEDRON LETT, V21, P1931
[6]  
BAKER BR, 1955, J ORG CHEM, V20, P118, DOI 10.1021/jo01119a019
[7]  
BIZOT J, 1967, B SOC CHIM FR, P151
[8]  
Boga C, 2001, EUR J ORG CHEM, V2001, P1175
[9]   DNA strand scission by the nephrotoxin [2,2'-bipyridine]-3,3',4,4'-tetrol-1,1'-dioxide and related compounds in the presence of iron [J].
Cantin-Esnault, D ;
Oubrahim, H ;
Richard, JM .
FREE RADICAL RESEARCH, 2000, 33 (02) :129-137
[10]  
DEHMLOW EV, 1987, LIEBIGS ANN CHEM, P857, DOI 10.1002/jlac.198719870840