ENANTIOSELECTIVE SYNTHESIS OF THE AB-RING FRAGMENT OF GAMBIERTOXIN-4B - IMPLICATION FOR THE ABSOLUTE-CONFIGURATION OF GAMBIERTOXIN-4B AND CIGUATOXIN

被引:74
作者
SUZUKI, T
SATO, O
HIRAMA, M
YAMAMOTO, Y
MURATA, M
YASUMOTO, T
HARADA, N
机构
[1] TOHOKU UNIV,FAC SCI,DEPT CHEM,SENDAI,MIYAGI 980,JAPAN
[2] TOHOKU UNIV,FAC AGR,SENDAI 981,JAPAN
[3] TOHOKU UNIV,INST CHEM REACT SCI,SENDAI,MIYAGI 980,JAPAN
关键词
CIGUATOXIN; GAMBIERTOXIN; ABSOLUTE CONFIGURATION; CD; ENANTIOSELECTIVE SYNTHESIS;
D O I
10.1016/0040-4039(91)80025-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The AB ring framework of gambiertoxin 4B which has a butadienyl substituent on the tetrahydrooxepin ring A has been synthesized stereoselectively and its CD spectrum suggests that gambiertoxin 4B and ciguatoxin have 5 R configuration.
引用
收藏
页码:4505 / 4508
页数:4
相关论文
共 7 条
  • [1] CATALYTIC ASYMMETRIC EPOXIDATION AND KINETIC RESOLUTION - MODIFIED PROCEDURES INCLUDING INSITU DERIVATIZATION
    GAO, Y
    HANSON, RM
    KLUNDER, JM
    KO, SY
    MASAMUNE, H
    SHARPLESS, KB
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (19) : 5765 - 5780
  • [2] STRUCTURES OF CIGUATOXIN AND ITS CONGENER
    MURATA, M
    LEGRAND, AM
    ISHIBASHI, Y
    YASUMOTO, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) : 8929 - 8931
  • [3] STRUCTURES AND CONFIGURATIONS OF CIGUATOXIN FROM THE MORAY EEL GYMNOTHORAX-JAVA']JAVANICUS AND ITS LIKELY PRECURSOR FROM THE DINOFLAGELLATE GAMBIERDISCUS-TOXICUS
    MURATA, M
    LEGRAND, AM
    ISHIBASHI, Y
    FUKUI, M
    YASUMOTO, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) : 4380 - 4386
  • [4] EFFICIENT METHODS FOR OXIDATION OF ALCOHOLS
    NARASAKA, K
    MORIKAWA, A
    SAIGO, K
    MUKAIYAMA, T
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (10) : 2773 - 2776
  • [5] REICH HG, 1982, J AM CHEM SOC, V85, P7051
  • [6] PALLADIUM CATALYZED STEREOSPECIFIC CYCLIZATION OF HYDROXY EPOXIDES - STEREOCONTROLLED SYNTHESIS OF CIS-2-ALKENYL AND TRANS-2-ALKENYL-3-HYDROXYTETRAHYDROPYRANS
    SUZUKI, T
    SATO, O
    HIRAMA, M
    [J]. TETRAHEDRON LETTERS, 1990, 31 (33) : 4747 - 4750
  • [7] A NEW APPROACH TO THE CONSTRUCTION OF BETA-ALKOXY-SUBSTITUTED CYCLIC ETHERS VIA THE INTRAMOLECULAR CYCLIZATION OF OMEGA-TRIALKYLPLUMBYL AND OMEGA-TRIALKYLSTANNYL ETHER ACETALS
    YAMADA, J
    ASANO, T
    KADOTA, I
    YAMAMOTO, Y
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) : 6066 - 6068