ACETOGENIC ISOQUINOLINE ALKALOIDS .69. BIOMIMETIC OXIDATIVE DIMERIZATION OF KORUPENSAMINE A - COMPLETION OF THE FIRST TOTAL SYNTHESIS OF MICHELLAMINE-A, MICHELLAMINE-B, AND MICHELLAMINE-C

被引:57
作者
BRINGMANN, G [1 ]
HARMSEN, S [1 ]
HOLENZ, J [1 ]
GEUDER, T [1 ]
GOTZ, R [1 ]
KELLER, PA [1 ]
WALTER, R [1 ]
HALLOCK, YF [1 ]
CARDELLINA, JH [1 ]
BOYD, MR [1 ]
机构
[1] NCI,DRUG DISCOVERY RES & DEV LAB,FREDERICK,MD 21702
关键词
D O I
10.1016/S0040-4020(01)85532-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A first synthetic access to michellamine A (1), a C-2-symmetric antiviral naturally occurring quateraryl, is described, by oxidative 'dimerization' of an appropriately protected 'monomeric' naphthylisoquinoline alkaloid, named korupensamine A (2). Due to the synthetic availability of 2 recently achieved and given the published interconversion of michellamines A - C, this coupling reaction simultaneously represents the completion of a first total synthesis of a representative and thus of all hitherto known michellamines.
引用
收藏
页码:9643 / 9648
页数:6
相关论文
共 15 条
[1]  
Barton D. H. R., 1957, FESTSCHRIFT A STOLL, P117
[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]  
BOYD MR, Patent No. 8049824
[4]  
BRINGMAN G, 1994, IN PRESS HETEROCYCLE
[5]  
BRINGMANN G, 1985, LIEBIGS ANN CHEM, P2126
[7]  
Bringmann G., 1986, ALKALOIDS, V29, P141
[8]  
BRINGMANN G, 1982, ANGEW CHEM, V94, P205
[9]  
BRINGMANN G, 1991, PLANTA MED S2, V57, P98
[10]  
HALLOCK YF, 1994, IN PRESS J ORG CHEM