Highly efficient synthesis of buflavine:: a unique Amaryllidaceae alkaloid

被引:17
作者
Sahakitpichan, P
Ruchirawat, S
机构
[1] Chulabhorn Res Inst, Bangkok 10210, Thailand
[2] Mahidol Univ, Fac Sci, Dept Chem, Bangkok 10400, Thailand
[3] Mahidol Univ, Chulabhorn Res Ctr, Inst Sci & Technol Res & Dev, Bangkok, Thailand
关键词
D O I
10.1016/S0040-4039(03)01207-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Amaryllidaceae alkaloid buflavine 1 has been synthesized in three steps by Suzuki-Miyaura cross coupling, reduction and the cascade reactions of Pictet-Spengler type and Eschweiler-Clarke N-methylation. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5239 / 5241
页数:3
相关论文
共 16 条
[1]   A modified in situ Suzuki cross-coupling of haloarenes for the preparation of C-2-symmetric biaryls [J].
Andersen, NG ;
Maddaford, SP ;
Keay, BA .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (26) :9556-9559
[2]   THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION [J].
COX, ED ;
COOK, JM .
CHEMICAL REVIEWS, 1995, 95 (06) :1797-1842
[3]   Total synthesis of amaryllidaceae alkaloid buflavine [J].
Hoarau, C ;
Couture, A ;
Deniau, E ;
Grandclaudon, P .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5846-5849
[4]  
ISHIDA Y, 1977, CHEM PHARM BULL, V25, P1851
[5]  
ISHIDA Y, 1985, J PHARMACOBIO-DYNAM, V8, P917
[6]  
KOBAYASHI S, 1977, CHEM PHARM BULL, V25, P3312
[7]   SYNTHESIS OF 1-AMINO-5-PHENYL-4,5-DIHYDRO-3H-2-BENZAZEPINES AND ISOMERIC 2-AMINO-1-BENZAZEPINES [J].
KUKLA, MJ .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (05) :933-935
[8]   Carbon-carbon bond forming solid-phase reactions [J].
Lorsbach, BA ;
Kurth, MJ .
CHEMICAL REVIEWS, 1999, 99 (06) :1549-1581
[9]  
MAURICE L, 1949, ORG REACTIONS, V5, P301
[10]   Directed ortho metalation -: Cross coupling connections.: Total synthesis of Amaryllidaceae alkaloids buflavine and 8-O-demethylbuflavine [J].
Patil, PA ;
Snieckus, V .
TETRAHEDRON LETTERS, 1998, 39 (11) :1325-1326