ACETOGENIC ISOQUINOLINE ALKALOIDS .17. 1ST TOTAL SYNTHESIS OF (-)-DIONCOPHYLLINE-A (TRIPHYOPHYLLINE) AND OF SELECTED STEREOISOMERS - COMPLETE (REVISED) STEREOSTRUCTURE

被引:79
作者
BRINGMANN, G [1 ]
JANSEN, JR [1 ]
REUSCHER, H [1 ]
RUBENACKER, M [1 ]
PETERS, K [1 ]
VONSCHNERING, HG [1 ]
机构
[1] MAX PLANCK INST FESTKORPERFORSCH,W-7000 STUTTGART 80,GERMANY
关键词
D O I
10.1016/S0040-4039(00)94589-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The first total synthesis of dioncophylline A (previously "triphyophylline") and some selected stereoisomers is described, using an intramolecular-type mixed aryl coupling method via ester-type prefixed molecular moieties. Simultaneously, this synthesis establishes the complete (revised) stereostructure of dioncophylline A as 1a, which is thereby the first fully elucidated naphthylisoquinoline alkaloid of Dioncophyllaceae. © 1990.
引用
收藏
页码:643 / 646
页数:4
相关论文
共 14 条
[1]   ACETOGENIC ISOQUINOLINE ALKALOIDS .12. CHIRAL ECONOMY WITH RESPECT TO ROTATIONAL-ISOMERISM - RATIONAL SYNTHESIS OF HAMATINE AND (OPTIONALLY) ANCISTROCLADINE FROM JOINT HELICAL PRECURSORS [J].
BRINGMANN, G ;
JANSEN, JR .
HETEROCYCLES, 1989, 28 (01) :137-142
[2]   A 1ST AND GENERAL-ROUTE TO NAPHTHYLISOQUINOLINE ALKALOIDS - THE TOTAL SYNTHESIS OF O-METHYL-TETRADEHYDRO-TRIPHYOPHYLLINE [J].
BRINGMANN, G ;
JANSEN, JR .
TETRAHEDRON LETTERS, 1984, 25 (24) :2537-2540
[3]   ACETOGENIC ISOQUINOLINE ALKALOIDS .16. ON THE STRUCTURE OF THE DIONCOPHYLLACEAE ALKALOIDS DIONCOPHYLLINE-A (TRIPHYOPHYLLINE) AND O-METHYL-TRIPHYOPHYLLINE [J].
BRINGMANN, G ;
RUBENACKER, M ;
JANSEN, JR ;
SCHEUTZOW, D ;
ASSI, LA .
TETRAHEDRON LETTERS, 1990, 31 (05) :639-642
[4]   ACETOGENIC ISOQUINOLINE ALKALOIDS .11. REGIOSELECTIVE AND ATROPOISOMERIC-SELECTIVE ARYL COUPLING TO GIVE NAPHTHYL ISOQUINOLINE ALKALOIDS - THE 1ST TOTAL SYNTHESIS OF (-)-ANCISTROCLADINE [J].
BRINGMANN, G ;
JANSEN, JR ;
RINK, HP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1986, 25 (10) :913-915
[5]  
Bringmann G., 1986, ALKALOIDS, V29, P141
[6]  
BRINGMANN G, 1986, ANGEW CHEM, V98, P917
[7]  
BRINGMANN G, 1989, ANGEW CHEM, V101
[8]  
BRINGMANN G, 1989, IN PRESS TETRAHEDRON, V30
[9]  
BRINGMANN G, 1988, 6EME S C INT CONS PL, P181
[10]   TRIPHYOPHYLLINE, NEW ALKALOID ISOLATED FROM TRIPHYOPHYLLUM-PELTATUM [J].
BRUNETON, J ;
BOUQUET, A ;
FOURNET, A ;
CAVE, A .
PHYTOCHEMISTRY, 1976, 15 (05) :817-818