CONSTRUCTION OF THE C46-C55 FRAGMENT OF CIGUATOXIN

被引:29
作者
OKA, T [1 ]
MURAI, A [1 ]
机构
[1] HOKKAIDO UNIV, FAC SCI, DEPT CHEM, SAPPORO 060, JAPAN
关键词
D O I
10.1246/cl.1994.1611
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The compound with all the necessary functional groups of the KLM ring system in ciguatoxin, which is one of the most complicated toxic substances of marine origin, was synthesized stereoselectively. The crucial steps involve construction of the ethynyl alcohol, the delta-valerolactone, and the natural acetals.
引用
收藏
页码:1611 / 1614
页数:4
相关论文
共 10 条
[1]   ON STEREOCHEMISTRY OF OSMIUM TETRAOXIDE OXIDATION OF ALLYLIC ALCOHOL SYSTEMS - EMPIRICAL RULE [J].
CHA, JK ;
CHRIST, WJ ;
KISHI, Y .
TETRAHEDRON, 1984, 40 (12) :2247-2255
[2]   STUDIES IN STEREOCHEMISTRY .10. THE RULE OF STERIC CONTROL OF ASYMMETRIC INDUCTION IN THE SYNTHESES OF ACYCLIC SYSTEMS [J].
CRAM, DJ ;
ELHAFEZ, FAA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (23) :5828-5835
[3]  
Inagawa J., 1979, B CHEM SOC JPN, V52, P1989
[4]   STRUCTURES AND CONFIGURATIONS OF CIGUATOXIN FROM THE MORAY EEL GYMNOTHORAX-JAVA']JAVANICUS AND ITS LIKELY PRECURSOR FROM THE DINOFLAGELLATE GAMBIERDISCUS-TOXICUS [J].
MURATA, M ;
LEGRAND, AM ;
ISHIBASHI, Y ;
FUKUI, M ;
YASUMOTO, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4380-4386
[5]   FURTHER SYNTHETIC STUDIES ON RIFAMYCIN-S [J].
NAGAOKA, H ;
KISHI, Y .
TETRAHEDRON, 1981, 37 (23) :3873-3888
[6]   HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].
OHTANI, I ;
KUSUMI, T ;
KASHMAN, Y ;
KAKISAWA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096
[7]   SYNTHETIC STUDIES TOWARD CIGUATOXIN - STEREOCONTROLLED CONSTRUCTION OF THE KLM RING FRAGMENT [J].
SASAKI, M ;
INOUE, M ;
TACHIBANA, K .
JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (04) :715-717
[8]   THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION - A NEW LIGAND CLASS AND A PROCESS IMPROVEMENT [J].
SHARPLESS, KB ;
AMBERG, W ;
BENNANI, YL ;
CRISPINO, GA ;
HARTUNG, J ;
JEONG, KS ;
KWONG, HL ;
MORIKAWA, K ;
WANG, ZM ;
XU, DQ ;
ZHANG, XL .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (10) :2768-2771
[9]  
SUZUKI T, 1983, TETRAHEDRON, V24, P1377
[10]  
1994, 67TH ANN M CHEM SOC