Synthesis of (-)- and (+)-8-fluoro-galanthamine

被引:9
作者
Knesl, Petr
Yousefi, Behrooz H.
Mereiter, Kurt
Jordis, Ulrich
机构
[1] Vienna Univ Technol, Inst Appl Synth CHem, A-1060 Vienna, Austria
[2] Vienna Univ Technol, Inst Chem Technol & Analyt, A-1060 Vienna, Austria
关键词
D O I
10.1016/j.tetlet.2006.06.010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of racemic 8-fluorogalanthamine and its separation into (-)- and (+)-8-fluorogalanthamine (= (4aS,6R, 8aS)- and(4aR,6S,8aR)-1-fluoro-4a,5,9,10,11,12-hexahydro-3-methoxy-11-methyl-6H-benzofuro[3a,3,2-ef][2]benzazepin-6-ol) is described. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5701 / 5703
页数:3
相关论文
共 10 条
[1]  
ABDUSAMATOV A, 1969, KHIM PRIR SOEDIN, V5, P194
[2]  
Czollner L., 2005, Int. Patent, Patent No. [WO2005/030333, 2005030333, WO 2005/030333 A2]
[3]  
CZOLLNER L, 1997, Patent No. 9740049
[4]  
KOBAYASHI S, 1956, CHEM IND-LONDON, P177
[5]   Development of a pilot scale process for the anti-Alzheimer drug (-)-galanthamine using large-scale phenolic oxidative coupling and crystallisation-induced chiral conversion [J].
Küenburg, B ;
Czollner, L ;
Fröhlich, J ;
Jordis, U .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 1999, 3 (06) :425-431
[6]   Allosteric modulation of nicotinic acetylcholine receptors as a treatment strategy for Alzheimer's disease [J].
Maelicke, A ;
Albuquerque, EX .
EUROPEAN JOURNAL OF PHARMACOLOGY, 2000, 393 (1-3) :165-170
[7]  
Makleit S, 2000, ACH-MODELS CHEM, V137, P447
[8]   Synthesis and pharmacology of galantamine [J].
Marco-Contelles, J ;
Carreiras, MD ;
Rodríguez, C ;
Villarroya, M ;
García, AG .
CHEMICAL REVIEWS, 2006, 106 (01) :116-133
[9]   (-)-galanthaminium bromide [J].
Peeters, OM ;
Blaton, NM ;
DeRanter, CJ .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1997, 53 :1284-1286
[10]   Review of the acetylcholinesterase inhibitor galanthamine [J].
Sramek, JJ ;
Frackiewicz, EJ ;
Cutler, NR .
EXPERT OPINION ON INVESTIGATIONAL DRUGS, 2000, 9 (10) :2393-2402