FACILE SYNTHESIS OF (+/-)-GALANTHAMINE AND (-)-GALANTHAMINE

被引:38
作者
SZEWCZYK, J
WILSON, JW
LEWIN, AH
CARROLL, FI
机构
[1] Chemistry and Life Sciences, Research Triangle Institute, Research Triangle Park, North Carolina, 27709
关键词
D O I
10.1002/jhet.5570320132
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Amarylidacea alkaloid galanthamine (1a) is an acetylcholinesterase inhibitor that has been evaluated as a potential agent for the treatment of Alzheimer's disease. We report a very efficient synthesis of (+/-)-galanthamine [(+/-)-1a] from readily available isovanillin and tyramine. We have separated racemic galanthamine into its diastereoisomeric (1S)-camphanate esters and obtained both natural (-)- and unnatural (+)-galanthamine by lithium aluminum hydride removal of the acyl group.
引用
收藏
页码:195 / 199
页数:5
相关论文
共 15 条
[1]   PHENOL OXIDATION AND BIOSYNTHESIS .5. SYNTHESIS OF GALANTHAMINE [J].
BARTON, DHR ;
KIRBY, GW .
JOURNAL OF THE CHEMICAL SOCIETY, 1962, (MAR) :806-&
[2]  
BECKER RE, 1991, CHOLINERGIC BASIS AL
[3]  
BOISSIER JR, 1962, EXTRAIT ANN PHARM FR, V20, P150
[4]  
DOMINO EF, 1988, CURRENT RES ALZHEIME, P295
[5]   A CONTROLLED TRIAL OF TACRINE IN ALZHEIMERS-DISEASE [J].
FARLOW, M ;
GRACON, SI ;
HERSHEY, LA ;
LEWIS, KW ;
SADOWSKY, CH ;
DOLANURENO, J .
JAMA-JOURNAL OF THE AMERICAN MEDICAL ASSOCIATION, 1992, 268 (18) :2523-2529
[6]  
IRWIN RL, 1960, ARCH INT PHARMACOD T, V127, P314
[7]   CHOLINESTERASE INHIBITION BY GALANTHAMINE AND LYCORAMINE [J].
IRWIN, RL ;
SMITH, HJ .
BIOCHEMICAL PHARMACOLOGY, 1960, 3 (02) :147-148
[8]   OPTICAL RESOLUTION OF (+/-)-GALANTHAMINE [J].
KAMETANI, T ;
PREMILA, MS ;
FUKUMOTO, K .
HETEROCYCLES, 1976, 4 (06) :1111-1114
[9]   STUDIES ON SYNTHESES OF HETEROCYCLIC COMPOUNDS .396. ALTERNATIVE TOTAL SYNTHESIS OF (+/-)-GALANTHAMINE [J].
KAMETANI, T ;
SHISHIDO, K ;
HAYASHI, E ;
SEINO, C ;
KOHNO, T ;
SHIBUYA, S ;
FUKUMOTO, K .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (09) :1295-&
[10]   STUDIES ON SYNTHESES OF HETEROCYCLIC COMPOUNDS .315. MODIFIED TOTAL SYNTHESIS OF (+-)-GALANTHAMINE THROUGH PHENOL OXIDATION [J].
KAMETANI, T ;
YAMAKI, K ;
YAGI, H ;
FUKUMOTO, K .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (18) :2602-&