MODEL STUDIES PROBING THE AMINO-CLAISEN REARRANGEMENT APPROACH TO HYDROISOQUINOLINE SYNTHESIS - DEVELOPMENT OF METHODS FOR STEREOCONTROLLED INTRODUCTION OF RESERPINE-E RING-TYPE FUNCTIONALITY

被引:30
作者
BAXTER, EW [1 ]
LABAREE, D [1 ]
CHAO, S [1 ]
MARIANO, PS [1 ]
机构
[1] UNIV MARYLAND,DEPT CHEM & BIOCHEM,COLLEGE PK,MD 20742
关键词
D O I
10.1021/jo00273a024
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
引用
收藏
页码:2893 / 2904
页数:12
相关论文
共 29 条
[1]  
Buchi G, 1970, J Am Chem Soc, V92, P999
[2]   A NEW ISOQUINUCLIDINE SYNTHESIS . A NEW ROUTE TO DL-DIOSCORONE [J].
CAVA, MP ;
WILKINS, CK ;
DALTON, DR ;
BESSHO, K .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (11) :3772-&
[3]   RAUWOLFIA ALKALOID SYNTHESIS APPROACH EMPLOYING THE ZWITTERIONIC AMINO-CLAISEN REARRANGEMENT - IMPROVEMENTS IN THE EFFICIENCY FOR YOHIMBANE RING CONSTRUCTION AND UNAMBIGUOUS DE-RING-FUSION STEREOCHEMICAL ASSIGNMENTS [J].
CHAO, S ;
KUNNG, FA ;
GU, JM ;
AMMON, HL ;
MARIANO, PS .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (15) :2708-2711
[4]  
CHEN Y, 1983, TETRAHEDRON LETT, P1021
[5]   SELECTIVITY IN BETA-ENAMINO KETONE ANION GENERATION AND ALKYLATION [J].
CHEN, YL ;
MARIANO, PS ;
LITTLE, GM ;
OBRIEN, D ;
HUESMANN, PL .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (23) :4643-4654
[6]  
FOWLER FW, 1972, J ORG CHEM, V37, P1321
[7]   ALLYLIC STRAIN IN 6-MEMBERED RINGS [J].
JOHNSON, F .
CHEMICAL REVIEWS, 1968, 68 (04) :375-+
[9]   HIGH-PRESSURE DIELS-ALDER REACTIONS OF FURANS WITH ALPHA-CHLOROXYACRYLONITRILE AND ALPHA-ACETOXYACRYLONITRILE [J].
KOTSUKI, H ;
NISHIZAWA, H .
HETEROCYCLES, 1981, 16 (08) :1287-1290
[10]   A NOVEL SYNTHETIC APPROACH TO RESERPINE BASED UPON AMINO-CLAISEN REARRANGEMENTS OF ZWITTERIONIC N-VINYLISOQUINUCLIDENES [J].
KUNNG, FA ;
GU, JM ;
CHAO, SC ;
CHEN, YP ;
MARIANO, PS .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (23) :4262-4266