Convergent synthesis of the EFGH ring fragment of ciguatoxin CTX3C

被引:44
作者
Imai, H
Uehara, H
Inoue, M
Oguri, H
Oishi, T
Hirama, M [1 ]
机构
[1] Tohoku Univ, Dept Chem, Grad Sch Sci, Sendai, Miyagi 9808578, Japan
[2] Japan Sci & Technol Corp, CREST, Sendai, Miyagi 9808578, Japan
关键词
ring-closing metathesis; acetal cleavage; radical reaction; ciguatoxin; polyethers; stereocontrolled synthesis;
D O I
10.1016/S0040-4039(01)01219-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A stereoselective synthesis of the EFGH ring fragment of ciguatoxin CTX3C has been achieved through: (i) selective cleavage of a dioxepane acetal C O bond; (ii) radical cyclization to form the oxepane G ring; and (iii) chemoselective ring-closing metathesis of a triene yielding the hexahydrooxonin F ring. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6219 / 6222
页数:4
相关论文
共 43 条
[1]   USEFUL DESIGNS IN THE SYNTHESIS OF TRANS-FUSED POLYETHER TOXINS [J].
ALVAREZ, E ;
CANDENAS, ML ;
PEREZ, R ;
RAVELO, JL ;
MARTIN, JD .
CHEMICAL REVIEWS, 1995, 95 (06) :1953-1980
[2]  
Armstrong SK, 1998, J CHEM SOC PERK T 1, P371
[3]  
Clark JS, 2000, ANGEW CHEM INT EDIT, V39, P372, DOI 10.1002/(SICI)1521-3773(20000117)39:2<372::AID-ANIE372>3.0.CO
[4]  
2-Y
[5]   A short synthesis of the A/B ring systems of the Pacific ciguatoxins P-CTX-3C and dihydroxy-P-CTX-3C [J].
Eriksson, L ;
Guy, S ;
Perlmutter, P ;
Lewis, R .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (22) :8396-8398
[6]   Asymmetric synthesis of the A-ring part of ciguatoxin by the strategy based on diastereoselective hydroboration and ring closing metathesis [J].
Fujiwara, K ;
Tanaka, H ;
Murai, A .
CHEMISTRY LETTERS, 2000, (06) :610-611
[7]  
FUKUZAWA S, 1995, SYNLETT, P1077
[8]   Recent advances in olefin metathesis and its application in organic synthesis [J].
Grubbs, RH ;
Chang, S .
TETRAHEDRON, 1998, 54 (18) :4413-4450
[9]   Construction of fused oxonene ring and reproduction of conformational behavior shown by ring F of ciguatoxin [J].
Inoue, M ;
Sasaki, M ;
Tachibana, K .
TETRAHEDRON LETTERS, 1997, 38 (09) :1611-1614
[10]   A convergent synthesis of the trans-fused hexahydrooxonine ring system and reproduction of conformational behavior shown by ring F of ciguatoxin [J].
Inoue, M ;
Sasaki, M ;
Tachibana, K .
TETRAHEDRON, 1999, 55 (36) :10949-10970