Diastereoselective photochemical synthesis of 3,3'-disubstituted indolines

被引:12
作者
IbrahimOuali, M
Sinibaldi, ME
Troin, Y
Guillaume, D
Gramain, JC
机构
[1] SEESIB,UMR 6504,F-63177 AUBIERE,FRANCE
[2] ENSCCF,LAB CHIM HETEROCYCLES & GLUCIDES,F-63174 AUBIERE,FRANCE
[3] UNIV PARIS 05,FAC SCI PHARMACEUT & BIOL,CNRS,URA 1310,F-75270 PARIS 06,FRANCE
关键词
D O I
10.1016/S0040-4020(97)10028-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Spiroindoline lactams 9 and imides 11 were efficiently and diastereoselectively prepared by photocyclization of N-arylenaminolactams 8 and esters 5 respectively. Imides 11 were conveniently transformed into the known indolines 13 and 14 which are key intermediates for the synthesis of (+/-)-vindorosine and Aspidosperma alkaloids. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:16083 / 16096
页数:14
相关论文
共 30 条
[1]   THE UTILIZATION OF TUNNEL EFFECTS FOR MECHANISTIC STUDIES OF HYDROGEN TRANSFER-REACTIONS [J].
BARON, U ;
BARTELT, G ;
EYCHMULLER, A ;
GRELLMANN, KH ;
SCHMITT, U ;
TAUER, E ;
WELLER, H .
JOURNAL OF PHOTOCHEMISTRY, 1985, 28 (02) :187-195
[2]  
BISWAS KM, 1994, J CHEM SOC P1, P461
[3]   NONOXIDATIVE PHOTOCYCLIZATION OF N-ARYL ENAMINES - FACILE SYNTHETIC ENTRY TO TRANS-HEXAHYDROCARBAZOLES [J].
CHAPMAN, OL ;
EIAN, GL ;
BLOOM, A ;
CLARDY, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) :2918-&
[4]   SYNTHETIC STUDIES ON INDOLE ALKALOIDS .6. SYNTHESIS OF TETRAHYDROAKUAMMICINE AND DIHYDROCORYNANTHEOL VIA 2-(3-INDOLYL)-4-PIPERIDONES [J].
DIEZ, A ;
VILA, C ;
SINIBALDI, ME ;
TROIN, Y ;
RUBIRALTA, M .
TETRAHEDRON LETTERS, 1993, 34 (04) :733-736
[5]   DIASTEREOSELECTIVE SPIROCYCLIZATION OF C-(ALKYLOXYCARBONYL)FORMIMINES OF 2-SUBSTITUTED 1H-INDOLE-3-ETHANAMINES (= TRYPTAMINES) - BASIC STUDIES .5. INDOLES, INDOLENINES, AND INDOLINES [J].
FREUND, R ;
MAHBOOBI, S ;
NOACK, K ;
SCHONHOLZER, P ;
BERNAUER, K .
HELVETICA CHIMICA ACTA, 1990, 73 (02) :439-454
[6]   STEREOSPECIFIC SYNTHESIS OF TRANS-1,2,3,4,4A,9A-HEXAHYDROCARBAZOL-4-ONES SUBSTITUTED IN 4A [J].
GRAMAIN, JC ;
HUSSON, HP ;
TROIN, Y .
TETRAHEDRON LETTERS, 1985, 26 (19) :2323-2326
[7]   STEREOCHEMISTRY OF REMOTE DIANION ADDITION TO IMINES - APPLICATION TO THE SYNTHESIS OF (1S, 8AS)-1-HYDROXYINDOLIZIDINE [J].
GREEN, DLC ;
KIDDLE, JJ ;
THOMPSON, CM .
TETRAHEDRON, 1995, 51 (10) :2865-2874
[8]  
GRELLMANN KH, 1963, J AM CHEM SOC, V85, P1181
[9]   PALLADIUM-CATALYZED SYNTHESIS OF SPIROINDOLINES [J].
GRIGG, R ;
FRETWELL, P ;
MEERHOLTZ, C ;
SRIDHARAN, V .
TETRAHEDRON, 1994, 50 (02) :359-370
[10]  
IBRAHIMOUALI M, 1995, HETEROCYCLES, V41, P1939