Chiral synthesis of the BC-ring system of ciguatoxin from D-glucose

被引:13
作者
Ami, E
Kishimoto, H
Ohrui, H
Meguro, H
机构
[1] Tohoku Univ, Fac Agr, Dept Appl Biol Chem, Aoba Ku, Sendai, Miyagi 981, Japan
[2] Sumitomo Pharmaceut Co Ltd, Konohana Ku, Osaka 554, Japan
关键词
ciguatoxin; chiral synthesis; D-glucose;
D O I
10.1271/bbb.61.2019
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The BC-ring system of ciguatoxin was stereoselectively synthesized by 12 steps from methyl alpha-D-glucopyranoside.
引用
收藏
页码:2019 / 2024
页数:6
相关论文
共 22 条
  • [1] A concise synthesis of ortho-condensed oxane-oxene, oxepene, oxocene and oxonene ring systems
    Alvarez, E
    Delgado, M
    Diaz, MT
    Liu, HX
    Perez, R
    Martin, JD
    [J]. TETRAHEDRON LETTERS, 1996, 37 (16) : 2865 - 2868
  • [2] HOSOKAWA S, 1995, SYNLETT, P1179
  • [3] Construction of fused oxonene ring and reproduction of conformational behavior shown by ring F of ciguatoxin
    Inoue, M
    Sasaki, M
    Tachibana, K
    [J]. TETRAHEDRON LETTERS, 1997, 38 (09) : 1611 - 1614
  • [4] syn-trans fused bicyclic ether formation via acetylene-biscobalthexacarbonyl complex
    Isobe, M
    Hosokawa, S
    Kira, K
    [J]. CHEMISTRY LETTERS, 1996, (06) : 473 - 474
  • [5] REGIOSELECTIVE REDUCTIVE RING-OPENING OF 4-METHOXYBENZYLIDENE ACETALS OF HEXOPYRANOSIDES - ACCESS TO A NOVEL PROTECTING-GROUP STRATEGY .1.
    JOHANSSON, R
    SAMUELSSON, B
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (10): : 2371 - 2374
  • [6] KISHIMOTO H, 1993, 35TH S CHEM NAT PROD, P112
  • [7] STEREOSELECTIVE RING-CLEAVAGE OF 3-O-BENZYL-4,6-O-BENZYLIDENEHEXOPYRANOSIDE AND 2,3-DI-O-BENZYL-4,6-O-BENZYLIDENEHEXOPYRANOSIDE DERIVATIVES WITH LIALH4-ALCL3 REAGENT
    LIPTAK, A
    JODAL, I
    NANASI, P
    [J]. CARBOHYDRATE RESEARCH, 1975, 44 (01) : 1 - 11
  • [8] 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
  • [9] 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
  • [10] Synthetic study of ciguatoxin. Absolute configuration of the C2 hydroxy group
    Oguri, H
    Hishiyama, S
    Sato, O
    Oishi, T
    Hirama, M
    Murata, M
    Yasumoto, T
    Harada, N
    [J]. TETRAHEDRON, 1997, 53 (09) : 3057 - 3072