Convergent synthesis of the BCDE-ring part of ciguatoxin

被引:32
作者
Fujiwara, K [1 ]
Koyama, Y [1 ]
Kawai, K [1 ]
Tanaka, H [1 ]
Murai, A [1 ]
机构
[1] Hokkaido Univ, Grad Sch Sci, Div Chem, Sapporo, Hokkaido 0600810, Japan
关键词
heterocycles; stereoselective synthesis; natural products; polyethers; polycycles;
D O I
10.1055/s-2002-34904
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The BCDE-ring part of ciguatoxin has been convergently synthesized by a sequence of reactions involving coupling of the E-ring part having a Z-enal group with the B-ring part as an acyl anion equivalent, selective removal of a p-bromobenzyl protective group using Miyaura's conditions, and reductive cyclization.
引用
收藏
页码:1835 / 1838
页数:4
相关论文
共 62 条
[1]   Simple designs for the construction of complex trans-fused polyether toxin frameworks. A convergent strategy based on hydroxy ketone cyclization of C-linked oxacycles [J].
Alvarez, E ;
Perez, R ;
Rico, M ;
Rodriguez, RM ;
Martin, JD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) :3003-3016
[2]   SYNTHESIS OF UNSATURATED TRANS-FUSED POLYETHER FRAMEWORKS VIA O-LINKED OXACYCLES - A CONVERGENT APPROACH [J].
ALVAREZ, E ;
DIAZ, MT ;
HANXING, L ;
MARTIN, JD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (04) :1437-1438
[3]  
Atsuta H, 1997, SYNLETT, P307
[4]  
BIDARD JN, 1984, J BIOL CHEM, V259, P8353
[5]   Synthesis of a ring F building block for the ciguatoxins [J].
Bond, S ;
Perlmutter, P .
TETRAHEDRON, 2002, 58 (10) :1779-1787
[6]   Synthesis and biological studies of flexible brevetoxin/ciguatoxin models with marked conformational preference [J].
Candenas, ML ;
Pinto, FM ;
Cintado, CG ;
Morales, EQ ;
Brouard, I ;
Díaz, MT ;
Rico, M ;
Rodríguez, E ;
Rodríguez, RM ;
Pérez, R ;
Pérez, RL ;
Martín, JD .
TETRAHEDRON, 2002, 58 (10) :1921-1942
[7]  
COREY EJ, 1972, TETRAHEDRON LETT, P3769
[8]   Ciguatoxins and brevetoxins, neurotoxic polyether compounds active on sodium channels [J].
Dechraoui, MY ;
Naar, J ;
Pauillac, S ;
Legrand, AM .
TOXICON, 1999, 37 (01) :125-143
[9]  
Díaz MT, 2001, SYNLETT, P345
[10]  
Fujiwara K, 2002, SYNLETT, P1496