Total synthesis of amaryllidaceae alkaloid buflavine

被引:28
作者
Hoarau, C [1 ]
Couture, A [1 ]
Deniau, E [1 ]
Grandclaudon, P [1 ]
机构
[1] Univ Sci & Tech Lille Flandres Artois, UPRESA 8009, Chim Organ Phys Lab, DUSVA, F-59655 Villeneuve Dascq, France
关键词
D O I
10.1021/jo0202379
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A concise synthesis of the amaryllidaceae alkaloid buflavine (1) and its regioisomer (2) involving sequential Meyers' biaryl coupling, enecarbamate formation, and hydrogenation followed by ultimate intramolecular reductive amination is presented.
引用
收藏
页码:5846 / 5849
页数:4
相关论文
共 21 条
[1]   Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures [J].
AbdelMagid, AF ;
Carson, KG ;
Harris, BD ;
Maryanoff, CA ;
Shah, RD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3849-3862
[2]   2,4-DIAMINO-6,7-DIMETHOXYQUINAZOLINES .1. 2-[4-(1,4-BENZODIOXAN-2-YLCARBONYL)PIPERAZIN-1-YL] DERIVATIVES AS ALPHA-1-ADRENOCEPTOR ANTAGONISTS AND ANTIHYPERTENSIVE AGENTS [J].
CAMPBELL, SF ;
DAVEY, MJ ;
HARDSTONE, JD ;
LEWIS, BN ;
PALMER, MJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (01) :49-57
[3]   A new approach to isoindolobenzazepines. A simple synthesis of lennoxamine [J].
Couture, A ;
Deniau, E ;
Grandclaudon, P ;
Hoarau, C .
TETRAHEDRON, 2000, 56 (11) :1491-1499
[4]   Dramatically different photochemical behaviour of 1-aroyl-2-methylene piperidine and pyrrolidine derivatives. An expeditious synthesis of ruspolinone [J].
Couture, A ;
Deniau, E ;
Grandclaudon, P ;
Lebrun, S .
TETRAHEDRON LETTERS, 1996, 37 (43) :7749-7752
[5]   First synthesis and pharmacological evaluation of benzoindolizidine and benzoquinolizidine analogues of α- and β-peltatin [J].
Couture, A ;
Deniau, E ;
Grandclaudon, P ;
Lebrun, S ;
Léonce, S ;
Renard, P ;
Pfeiffer, B .
BIOORGANIC & MEDICINAL CHEMISTRY, 2000, 8 (08) :2113-2125
[6]   A concise total synthesis of the azaphenanthrene alkaloid eupolauramine [J].
Hoarau, C ;
Couture, A ;
Cornet, H ;
Deniau, E ;
Grandclaudon, P .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :8064-8069
[7]  
HOARAU C, 1998, J ORG CHEM, V63, P3128
[8]   An oxazoline-mediated synthesis of the pyrrolophenanthridine alkaloids and some novel derivatives [J].
Hutchings, RH ;
Meyers, AI .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (03) :1004-1013
[9]  
ISHIDA Y, 1985, J PHARMACOBIO-DYNAM, V8, P917
[10]  
ISHIDA Y, 1986, CHEM ABSTR, V104, P45660