Enantioselective total synthesis of (-)-galanthamine

被引:148
作者
Trost, BM [1 ]
Toste, FD [1 ]
机构
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
关键词
D O I
10.1021/ja002231b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
引用
收藏
页码:11262 / 11263
页数:2
相关论文
共 52 条
[1]   USE OF THE ELECTROPHILIC ARYLATION REACTION OF ARYL-LEAD TRIACETATES IN A SYNTHESIS OF (+/-)-LYCORAMINE [J].
ACKLAND, DJ ;
PINHEY, JT .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (12) :2695-2700
[2]   NUCLEOPHILIC-SUBSTITUTION OF FUNCTIONAL ALLYLIC CYCLOALKENOL ACETATES BY ORGANOMETAL COMPOUNDS IN THE PRESENCE OF COPPER-SALTS - APPLICATION TO RAPID SYNTHESIS OF MITSUGASHIWALACTONE [J].
AMRI, H ;
RAMBAUD, M ;
VILLIERAS, J .
TETRAHEDRON, 1990, 46 (10) :3535-3546
[3]   EPOXIDATION OF PRIMARY AND SECONDARY ALKENYLAMMONIUM SALTS WITH DIMETHYLDIOXIRANE, METHYL(TRIFLUOROMETHYL) DIOXIRANE, AND M-CHLOROPERBENZOIC ACID - A GENERAL SYNTHETIC ROUTE TO EPOXYALKYLAMINES [J].
ASENSIO, G ;
MELLO, R ;
BOIXBERNARDINI, C ;
GONZALEZNUNEZ, ME ;
CASTELLANO, G .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (12) :3692-3699
[4]   PHENOL OXIDATION AND BIOSYNTHESIS .5. SYNTHESIS OF GALANTHAMINE [J].
BARTON, DHR ;
KIRBY, GW .
JOURNAL OF THE CHEMICAL SOCIETY, 1962, (MAR) :806-&
[5]   Isomerization of allylic silyl ethers catalyzed by ReO3(OSiR3) complexes [J].
Bellemin-Laponnaz, S ;
Le Ny, JP ;
Osborn, JA .
TETRAHEDRON LETTERS, 2000, 41 (10) :1549-1552
[6]   Mechanistic insights into the very efficient [ReO3OSiR3]-catalyzed isomerization of allyl alcohols [J].
Bellemin-Laponnaz, S ;
Gisie, H ;
LeNy, JP ;
Osborn, JA .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1997, 36 (09) :976-978
[7]   Dynamic diastereomeric salt resolution of narwedine and its transformation to (-)-galanthamine [J].
Chaplin, DA ;
Johnson, NB ;
Paul, JM ;
Potter, GA .
TETRAHEDRON LETTERS, 1998, 39 (37) :6777-6780
[8]   A concise, scaleable synthesis of narwedine [J].
Chaplin, DA ;
Fraser, N ;
Tiffin, PD .
TETRAHEDRON LETTERS, 1997, 38 (45) :7931-7932
[9]   New kilogram-synthesis of the anti-Alzheimer drug (-)-galanthamine [J].
Czollner, L ;
Frantsits, W ;
Küenburg, B ;
Hedenig, U ;
Fröhlich, J ;
Jordis, U .
TETRAHEDRON LETTERS, 1998, 39 (15) :2087-2088
[10]   Model study for a general approach to morphine and noroxymorphone via a rare heck cyclization [J].
Frey, DA ;
Duan, CM ;
Hudlicky, T .
ORGANIC LETTERS, 1999, 1 (13) :2085-2087