ACETOGENIC ISOQUINOLINE ALKALOIDS .72. (1R,3R)-1,3-DIMETHYL-8-HYDROXY-6-METHOXY-1,2,3,4-TETRAHYDROISOQUINOLINE HYDROCHLORIDE - AN ENANTIOMERICALLY PURE BUILDING-BLOCK FOR THE SYNTHESIS OF NAPHTHYLISOQUINOLINE ALKALOIDS

被引:1
作者
PETERS, K [1 ]
PETERS, EM [1 ]
BRINGMANN, G [1 ]
KELLER, PA [1 ]
SCHAFFER, M [1 ]
机构
[1] UNIV WURZBURG,INST ORGAN CHEM,D-97074 WURZBURG,GERMANY
来源
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES | 1995年 / 50卷 / 07期
关键词
CRYSTAL STRUCTURE; NAPHTHYLISOQUINOLINE ALKALOIDS; STEREOCHEMISTRY;
D O I
10.1515/znb-1995-0729
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The title compound was prepared by hydrogenolytic deprotection of the corresponding N-benzyl derivative, which had previously been synthesized by a Picted-Spengler condensation of the corresponding arylethylamine. It crystallizes from dichloromethane/methanol in the orthorhombic system, space group P2(1)2(1)2(1); a = 1305.7(2), b = 1400.3(3), c = 727.4(1) pm. Hydrogen bonds between Cl and OH and NH2 groups cause a three-dimensional arrangement.
引用
收藏
页码:1137 / 1139
页数:3
相关论文
共 13 条
[1]  
[Anonymous], 1995, ALKALOIDS CHEM PHARM
[2]   ANTI-HIV MICHELLAMINES FROM ANCISTROCLADUS-KORUPENSIS [J].
BOYD, MR ;
HALLOCK, YF ;
MANFREDI, KP ;
BLUNT, JW ;
MCMAHON, JB ;
BUCKHEIT, RW ;
BRINGMANN, G ;
SCHAFFER, M ;
CRAGG, GM ;
THOMAS, DW ;
JATO, JG ;
CARDELLINA, JH .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (12) :1740-1745
[3]   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
[4]   ACETOGENIC ISOQUINOLINE ALKALOIDS .69. BIOMIMETIC OXIDATIVE DIMERIZATION OF KORUPENSAMINE A - COMPLETION OF THE FIRST TOTAL SYNTHESIS OF MICHELLAMINE-A, MICHELLAMINE-B, AND MICHELLAMINE-C [J].
BRINGMANN, G ;
HARMSEN, S ;
HOLENZ, J ;
GEUDER, T ;
GOTZ, R ;
KELLER, PA ;
WALTER, R ;
HALLOCK, YF ;
CARDELLINA, JH ;
BOYD, MR .
TETRAHEDRON, 1994, 50 (32) :9643-9648
[5]  
BRINGMANN G, 1993, LIEBIGS ANN CHEM, P877
[6]   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
[7]  
BRINGMANN G, 1986, ANGEW CHEM, V98, P917
[8]   ACTIVITY OF EXTRACTS AND NAPHTHYLISOQUINOLINE ALKALOIDS FROM TRIPHYOPHYLLUM-PELTATUM, ANCISTROCLADUS-ABBREVIATUS AND A-BARTERI AGAINST PLASMODIUM-FALCIPARUM IN-VITRO [J].
FRANCOIS, G ;
BRINGMANN, G ;
PHILLIPSON, JD ;
ASSI, LA ;
DOCHEZ, C ;
RUBENACKER, M ;
SCHNEIDER, C ;
WERY, M ;
WARHURST, DC ;
KIRBY, GC .
PHYTOCHEMISTRY, 1994, 35 (06) :1461-1464
[9]  
FRANCOIS G, 1995, IN PRESS J ETHNOPHAR
[10]  
FRANCOIS G, 1994, UNPUB INT J PHARMACO