Reaction of indole-2,3-dicarboxylic anhydride with (3-bromo-4-pyridyl)triisopropoxytitanium: Synthesis of ellipticine

被引:33
作者
Miki, Y
Tada, Y
Yanase, N
Hachiken, H
Matsushita, K
机构
[1] Faculty of Pharmaceutical Sciences, Kinki University, Higashi-Osaka 577
关键词
D O I
10.1016/0040-4039(96)01768-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Benzylindole-2,3-dicarboxylic anhydride (1) was reacted with (3-bromo-4-pyridyl)triisopropoxytitanium to give 2-(3-bromoisonicotinoyl)indole-3-carboxylic acid (2) as the sole product in high yield, which could be converted to ellipticine in six steps. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:7753 / 7754
页数:2
相关论文
共 25 条
[1]  
[Anonymous], 1990, ADV HETEROCYCLIC NAT
[2]   SYNTHESIS OF TUMOUR-INHIBITORY ALKALOIDS ELLIPTICINE 9-METHOXYELLIPTICINE AND RELATED PYRIDO[4,3-B]CARBAZOLES [J].
DALTON, LK ;
DEMERAC, S ;
ELMES, BC ;
LODER, JW ;
SWAN, JM ;
TEITEI, T .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1967, 20 (12) :2715-&
[3]   A REGIOSELECTIVE DIELS-ALDER SYNTHESIS OF ELLIPTICINE [J].
DAVIS, DA ;
GRIBBLE, GW .
TETRAHEDRON LETTERS, 1990, 31 (08) :1081-1084
[4]   PREPARATION OF DIDEHYDROPYRIDINES FROM (TRIMETHYLSILYL)PYRIDINES [J].
EFFENBERGER, F ;
DAUB, W .
CHEMISCHE BERICHTE, 1991, 124 (09) :2119-2125
[5]  
GRIBBLE GW, 1985, HETEROCYCLES, V23, P1277
[6]  
GRIBBLE GW, 1991, SYNLETT, P289
[7]   SYNTHESIS AND DIELS-ALDER REACTIONS OF 1,3-DIMETHYL-4-(PHENYLSULFONYL)-4H-FURO[3,4-B]INDOLE - A NEW ANNULATION STRATEGY FOR THE CONSTRUCTION OF ELLIPTICINE AND ISOELLIPTICINE [J].
GRIBBLE, GW ;
SAULNIER, MG ;
SIBI, MP ;
OBAZANUTAITIS, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (23) :4518-4523
[8]   SYNTHESES AND DIELS-ALDER CYCLOADDITION REACTIONS OF 4H-FURO[3,4-B]INDOLES - A REGIOSPECIFIC DIELS-ALDER SYNTHESIS OF ELLIPTICINE [J].
GRIBBLE, GW ;
KEAVY, DJ ;
DAVIS, DA ;
SAULNIER, MG ;
PELCMAN, B ;
BARDEN, TC ;
SIBI, MP ;
OLSON, ER ;
BELBRUNO, JJ .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5878-5891
[9]   A VERSATILE AND EFFICIENT CONSTRUCTION OF THE 6H-PYRIDO[4,3-B]CARBAZOLE RING-SYSTEM - SYNTHESES OF THE ANTITUMOR ALKALOIDS ELLIPTICINE, 9-METHOXYELLIPTICINE, AND OLIVACINE AND THEIR ANALOGS [J].
GRIBBLE, GW ;
SAULNIER, MG ;
OBAZANUTAITIS, JA ;
KETCHA, DM .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (22) :5891-5899
[10]   Synthesis of 4-alkyl-3,5-dibromo-, 3-bromo-4,5-dialkyl- and 3,4,5-trialkylpyridines via sequential metalation and metal-halogen exchange of 3,5-dibromopyridine [J].
Gu, YG ;
Bayburt, EK .
TETRAHEDRON LETTERS, 1996, 37 (15) :2565-2568