ACETOGENIC ISOQUINOLINE ALKALOIDS .16. ON THE STRUCTURE OF THE DIONCOPHYLLACEAE ALKALOIDS DIONCOPHYLLINE-A (TRIPHYOPHYLLINE) AND O-METHYL-TRIPHYOPHYLLINE

被引:85
作者
BRINGMANN, G [1 ]
RUBENACKER, M [1 ]
JANSEN, JR [1 ]
SCHEUTZOW, D [1 ]
ASSI, LA [1 ]
机构
[1] UNIV ABIDJAN,CTR NATL FLORIST,ABIDJAN 22,COTE IVOIRE
关键词
D O I
10.1016/S0040-4039(00)94588-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The naphthyl isoquinoline alkaloid "triphyophylline" is structurally re-investigated. The constitution, as well as the relative configurations at C-1 and C-3, are confirmed as published previously. "Triphyophylline" is found to be a stable rotational isomer with respect to the biaryl linkage, the absolute configuration at the stereogenic axis is determined to be S. The data of the natural product "O-methyl-triphyophylline", as reported in the literature, are shown not to be identical with those of the O-methylation product of triphyophylline, as prepared by partial synthesis. This inconsistency within the published series of Dioncophyllaceae alkaloids necessitates to rename "triphyophylline" (new name: "dioncophylline A"). © 1990.
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页码:639 / 642
页数:4
相关论文
共 15 条
[1]   ACETOGENIC ISOQUINOLINE ALKALOIDS .17. 1ST TOTAL SYNTHESIS OF (-)-DIONCOPHYLLINE-A (TRIPHYOPHYLLINE) AND OF SELECTED STEREOISOMERS - COMPLETE (REVISED) STEREOSTRUCTURE [J].
BRINGMANN, G ;
JANSEN, JR ;
REUSCHER, H ;
RUBENACKER, M ;
PETERS, K ;
VONSCHNERING, HG .
TETRAHEDRON LETTERS, 1990, 31 (05) :643-646
[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]  
Bringmann G., 1986, ALKALOIDS, V29, P141
[4]  
BRINGMANN G, 1984, THESIS MUNSTER
[5]   TRIPHYOPHYLLINE, NEW ALKALOID ISOLATED FROM TRIPHYOPHYLLUM-PELTATUM [J].
BRUNETON, J ;
BOUQUET, A ;
FOURNET, A ;
CAVE, A .
PHYTOCHEMISTRY, 1976, 15 (05) :817-818
[6]   ABSOLUTE STEREOCHEMISTRY OF ANCISTROCLADINE AND ANCISTROCLADININE [J].
GOVINDAC.TR ;
NAGARAJA.K ;
PARTHASA.PC ;
RAJAGOPA.TG ;
DESAI, HK ;
KARTHA, G ;
LAI, CHEN, SM ;
NAKANISH.K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (12) :1413-1417
[7]  
GOVINDACHARI TR, 1974, J CHEM SOC P1, P2134
[8]   EXCITON CHIRALITY METHOD AND ITS APPLICATION TO CONFIGURATIONAL AND CONFORMATIONAL STUDIES OF NATURAL-PRODUCTS [J].
HARADA, N ;
NAKANISHI, K .
ACCOUNTS OF CHEMICAL RESEARCH, 1972, 5 (08) :257-+
[9]  
HEGNAUER R, 1989, CHEMOTAXONOMY PLANTS, V8, P338
[10]  
LAVAULT M, 1977, CR ACAD SCI C CHIM, V285, P167