CONVERGENT SYNTHESIS OF THE STREPTONIGRIN ALKALOID SKELETON - DIRECTED ORTHOMETALATION CONNECTION TO ARYL-ARYL CROSS-COUPLING

被引:40
作者
GODARD, A
ROVERA, JC
MARSAIS, F
PLE, N
QUEGUINER, G
机构
[1] Laboratoire de Chimie Organique Fine et Hétérocyclique de l'IRCOF, URA 1429, Institut National des Sciences Appliquées de Rouen, 76131 Mont-Saint-Aignan Cedex
关键词
STREPTONINGRIN; ALKALOID; METALATION; PALLADIUM; COUPLING;
D O I
10.1016/S0040-4020(01)92191-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convergent synthesis of 2-[2-(4-phenyl-3-pivaloylamino) pyridyl]quinolines, the streptonigrin alkaloid skeleton, is reported. The methodology involves independent elaboration of the three main building blocks by metalation and two coupling reactions catalyzed by palladium.
引用
收藏
页码:4123 / 4134
页数:12
相关论文
共 24 条
[1]   STREPTONIGRIN AND LAVENDAMYCIN PARTIAL STRUCTURES - PROBES FOR THE MINIMUM, POTENT PHARMACOPHORE OF STREPTONIGRIN, LAVENDAMYCIN, AND SYNTHETIC QUINOLINE-5,8-DIONES [J].
BOGER, DL ;
YASUDA, M ;
MITSCHER, LA ;
DRAKE, SD ;
KITOS, PA ;
THOMPSON, SC .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (10) :1918-1928
[2]  
BOGER DL, 1985, J AM CHEM SOC, V107, P5746
[3]   MOLECULAR AND CRYSTAL-STRUCTURE OF STREPTONIGRIN [J].
CHIU, YYH ;
LIPSCOMB, WN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (09) :2525-2530
[4]  
ECHEVARREN AM, 1987, J AM CHEM SOC, V109, P5478
[5]   SYNTHESIS OF ORTHO-SUBSTITUTED AMINOPYRIDINES - METALATION OF PIVALOYLAMINO DERIVATIVES [J].
ESTEL, L ;
LINARD, F ;
MARSAIS, F ;
GODARD, A ;
QUEGUINER, G .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1989, 26 (01) :105-112
[6]   CONNECTIONS TO THE DIRECTED ORTHO METALATION STRATEGY - PD(0)-CATALYZED CROSS COUPLING OF ARYL BORONIC ACIDS WITH ARYL TRIFLATES [J].
FU, JM ;
SNIECKUS, V .
TETRAHEDRON LETTERS, 1990, 31 (12) :1665-1668
[7]  
FURUKAWA N, Patent No. 6403169
[8]  
GUNGOR T, 1982, SYNTHESIS-STUTTGART, P499
[9]   SYNTHESIS OF DIARYLIC COMPOUNDS BY PALLADIUM CATALYZED REACTION OF AROMATIC TRIFLATES WITH BORONIC ACIDS [J].
HUTH, A ;
BEETZ, I ;
SCHUMANN, I .
TETRAHEDRON, 1989, 45 (21) :6679-6682
[10]  
ISHIKURA M, 1985, HETEROCYCLES, V23, P2375