A novel synthesis of isoindolobenzazepine alkaloids: application to the synthesis of lennoxamine

被引:30
作者
Ruchirawat, S
Sahakitpichan, P
机构
[1] Chulabhorn Res Inst, Bangkok 10210, Thailand
[2] Mahidol Univ, Fac Sci, Dept Chem, Bangkok 10400, Thailand
[3] Mahidol Univ, Inst Sci & Technol Res & Dev, Programme Res & Dev Synthet Drugs, Bangkok 10400, Thailand
关键词
lennoxamine; isoindolobenzazepine;
D O I
10.1016/S0040-4039(00)01390-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel, highly efficient synthesis of lennoxamine, a representative of isoindolobenzazepine alkaloid, is described. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8007 / 8010
页数:4
相关论文
共 25 条
[1]  
BERNHARD HO, 1971, TETRAHEDRON LETT, P4867
[2]   DECARBOXYLATION OF PHTHALIDECARBOXYLIC ACIDS IN THE PRESENCE OF IMINES - A FACILE ROUTE TO ISOINDOLO[1,2-B][3]BENZAZEPIN-5-ONES AND PHTHALIDEISOQUINOLINES [J].
CHIEFARI, J ;
JANOWSKI, W ;
PRAGER, R .
TETRAHEDRON LETTERS, 1986, 27 (50) :6119-6122
[3]   A new approach to isoindolobenzazepines. A simple synthesis of lennoxamine [J].
Couture, A ;
Deniau, E ;
Grandclaudon, P ;
Hoarau, C .
TETRAHEDRON, 2000, 56 (11) :1491-1499
[4]   IMINIUM SALTS FROM ALPHA-AMINO-ACID DECARBONYLATION - APPLICATION TO SYNTHESIS OF BERBINES [J].
DEAN, RT ;
RAPOPORT, H .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (11) :2115-2122
[5]  
DORN CR, 1984, J ORG CHEM, V49, P2642
[6]   CHILENINE - AN ISOINDOLOBENZAZEPINE ALKALOID [J].
FAJARDO, V ;
ELANGO, V ;
CASSELS, BK ;
SHAMMA, M .
TETRAHEDRON LETTERS, 1982, 23 (01) :39-42
[7]   THE TOTAL SYNTHESIS OF CHILENINE - NOVEL CONSTRUCTIONS OF CYCLIC ENAMIDES [J].
FANG, FG ;
DANISHEFSKY, SJ .
TETRAHEDRON LETTERS, 1989, 30 (21) :2747-2750
[8]  
ISHIBASHI H, 1995, TETRAHEDRON LETT, V36, P6733, DOI 10.1016/00404-0399(50)1364N-
[9]   Sulfur-controlled 5-exo selective aryl radical cyclisation of N-vinylic 2-bromobenzamides: Synthesis of lennoxamine and chilenine [J].
Ishibashi, H ;
Kawanami, H ;
Ikeda, M .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (06) :817-821
[10]  
KESSAR SV, 1991, INDIAN J CHEM B, V30, P299