Acetylene cobalt complex and vinylsilane strategy in the synthesis of ciguatoxin (D)EF analog

被引:46
作者
Kira, K [1 ]
Isobe, M [1 ]
机构
[1] Nagoya Univ, Grad Sch Bioagr Sci, Organ Chem Lab, Chikusa Ku, Nagoya, Aichi 4648601, Japan
关键词
ciguatoxin; acetylene cobalt complex; hydrosilylation; vinylsilane;
D O I
10.1016/S0040-4039(00)00988-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A synthetic route to the (D)EF analog of ciguatoxin has been explored through acetylene cobalt complex and vinylsilane strategy. The central reactions in the synthesis are: (i) ether ring formation mediated by acetylene cobalt complex and (ii) decomplexation of the endo-acetylene cobalt complexes to vinylsilanes or olefins. Unusual rearrangement of epoxy-silane to allylic alcohol is also described. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5951 / 5955
页数:5
相关论文
共 24 条
[11]   Stereocontrolled synthesis and reactivity of sugar acetylenes [J].
Isobe, M ;
Nishizawa, R ;
Hosokawa, S ;
Nishikawa, T .
CHEMICAL COMMUNICATIONS, 1998, (24) :2665-2676
[12]  
Leeuwenburgh MA, 1999, SYNLETT, P1945
[13]  
Liu TZ, 2000, SYNLETT, P587
[14]  
LIU TZ, IN PRESS TETRAHEDRON
[15]   Convergent synthesis of the ABCDE ring framework of ciguatoxin [J].
Maeda, K ;
Oishi, T ;
Oguri, H ;
Hirama, M .
CHEMICAL COMMUNICATIONS, 1999, (12) :1063-1064
[16]   Convergent synthesis of the trans-fused 6-n-6-6 (n = 7-10) tetracyclic ether system based on a ring-closing metathesis reaction [J].
Oishi, T ;
Nagumo, Y ;
Hirama, M .
CHEMICAL COMMUNICATIONS, 1998, (09) :1041-1042
[17]   Synthetic studies on ciguatoxin - [2]; Synthesis of the A,B,C-ring system [J].
Oka, T ;
Fujiwara, K ;
Murai, A .
TETRAHEDRON, 1998, 54 (1-2) :21-44
[18]   Partial synthesis of ciguatoxin (5R)-ABC segment [J].
Saeeng, R ;
Isobe, M .
TETRAHEDRON LETTERS, 1999, 40 (10) :1911-1914
[19]   A general method for convergent synthesis of polycyclic ethers based on Suzuki cross-coupling: Concise synthesis of the ABCD ring system of ciguatoxin [J].
Sasaki, M ;
Fuwa, H ;
Ishikawa, M ;
Tachibana, K .
ORGANIC LETTERS, 1999, 1 (07) :1075-1077
[20]   The absolute configuration of ciguatoxin [J].
Satake, M ;
Morohashi, A ;
Oguri, H ;
Oishi, T ;
Hirama, M ;
Harada, N ;
Yasumoto, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (46) :11325-11326