Synthetic studies on the HIJK-ring fragment of ciguatoxin

被引:35
作者
Liu, TZ [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
acetylene-biscobalthexacarbonyl; ciguatoxin; heteroconjugate addition; Sonogashira coupling; cyclization;
D O I
10.1016/S0040-4020(00)00467-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Synthesis of the tetracyclic HIJK-ring fragment of ciguatoxin with high stereoselectivity has been achieved starting from a sugar derivative directed toward the synthesis of the right part of ciguatoxin. Sonogashira coupling of a vinyl iodide with an acetylene derivative, cobalt complex-mediated (seven- and eight-membered ring) cyclizations and a heteroconjugate addition reaction play important roles in the current research work. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5391 / 5404
页数:14
相关论文
共 49 条
[21]   PURIFICATION AND CHARACTERIZATION OF CIGUATOXINS FROM MORAY EEL (LYCODONTIS-JAVA']JAVANICUS, MURAENIDAE) [J].
LEWIS, RJ ;
SELLIN, M ;
POLI, MA ;
NORTON, RS ;
MACLEOD, JK ;
SHEIL, MM .
TOXICON, 1991, 29 (09) :1115-1127
[22]   ISOLATION AND STRUCTURE OF BREVETOXIN-B FROM THE RED TIDE DINOFLAGELLATE PTYCHODISCUS-BREVIS (GYMNODINIUM, BREVE) [J].
LIN, YY ;
RISK, M ;
RAY, SM ;
VANENGEN, D ;
CLARDY, J ;
GOLIK, J ;
JAMES, JC ;
NAKANISHI, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (22) :6773-6775
[23]  
LIU TZ, 2000, UNPUB TETRAHEDRON
[24]   CIGUATOXIN AND BREVETOXINS SHARE A COMMON RECEPTOR-SITE ON THE NEURONAL VOLTAGE-DEPENDENT NA-(+) CHANNEL [J].
LOMBET, A ;
BIDARD, JN ;
LAZDUNSKI, M .
FEBS LETTERS, 1987, 219 (02) :355-359
[25]   Convergent synthesis of the ABCDE ring framework of ciguatoxin [J].
Maeda, K ;
Oishi, T ;
Oguri, H ;
Hirama, M .
CHEMICAL COMMUNICATIONS, 1999, (12) :1063-1064
[26]   OXIDATION OF LONG-CHAIN AND RELATED ALCOHOLS TO CARBONYLS BY DIMETHYL-SULFOXIDE ACTIVATED BY OXALYL CHLORIDE [J].
MANCUSO, AJ ;
HUANG, SL ;
SWERN, D .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (12) :2480-2482
[27]   C-13 NMR ASSIGNMENTS OF CIGUATOXIN BY INVERSE-DETECTED 2D-SPECTROSCOPY AND AN EXPLANATION OF NMR SIGNAL BROADENING [J].
MURATA, M ;
LEGRAND, AM ;
SCHEUER, PJ ;
YASUMOTO, T .
TETRAHEDRON LETTERS, 1992, 33 (04) :525-526
[28]   STRUCTURES OF CIGUATOXIN AND ITS CONGENER [J].
MURATA, M ;
LEGRAND, AM ;
ISHIBASHI, Y ;
YASUMOTO, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) :8929-8931
[29]   A PROBABLE PARTIAL STRUCTURE OF CIGUATOXIN ISOLATED FROM THE MORAY EEL GYMNOTHORAX-JAVA']JAVANICUS [J].
MURATA, M ;
LEGRAND, AM ;
YASUMOTO, T .
TETRAHEDRON LETTERS, 1989, 30 (29) :3793-3796
[30]  
Nicholas K. M., 1971, TETRAHEDRON LETT, V37, P3475