Synthetic study of ciguatoxin. Absolute configuration of the C2 hydroxy group

被引:53
作者
Oguri, H
Hishiyama, S
Sato, O
Oishi, T
Hirama, M
Murata, M
Yasumoto, T
Harada, N
机构
[1] TOHOKU UNIV,GRAD SCH SCI,DEPT CHEM,SENDAI,MIYAGI 98077,JAPAN
[2] TOHOKU UNIV,DEPT AGR,SENDAI,MIYAGI 98077,JAPAN
[3] TOHOKU UNIV,INST CHEM REACT SCI,SENDAI,MIYAGI 98077,JAPAN
关键词
D O I
10.1016/S0040-4020(97)00071-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The absolute stereochemistry of the secondary alcohol of the 1,2-dihydroxybutenyl substituent of ciguatoxin (1) was shown to be S by comparing the split CD curve of ciguatoxin tetra-p-bromobenzoate (2) with those of di- and tri-p-bromobenzoates of AB ring fragments that were synthesized enantioselectively. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:3057 / 3072
页数:16
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  • [1] Simple designs for the construction of complex trans-fused polyether toxin frameworks. A convergent strategy based on hydroxy ketone cyclization of C-linked oxacycles
    Alvarez, E
    Perez, R
    Rico, M
    Rodriguez, RM
    Martin, JD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) : 3003 - 3016
  • [2] SIMPLE DESIGNS FOR THE CONSTRUCTION OF COMPLEX TRANS-FUSED POLYETHER TOXIN FRAMEWORKS - A LINEAR STRATEGY BASED ON ENTROPICALLY FAVORED OXIRANE RING ENLARGEMENT IN EPOXYCYCLOALKENES FOLLOWED BY CARBON-CARBON OR CARBON-OXYGEN BOND-FORMING CYCLIZATIONS
    ALVAREZ, E
    DIAZ, MT
    PEREZ, R
    RAVELO, JL
    REGUEIRO, A
    VERA, JA
    ZURITA, D
    MARTIN, JD
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (10) : 2848 - 2876
  • [3] A UNIFIED STEREOCHEMICAL MODEL FOR THE POLYEPOXIDE CYCLIZATION ROUTE TO MARINE POLYETHER TOXINS
    ALVAREZ, E
    RODRIGUEZ, ML
    ZURITA, D
    MARTIN, JD
    [J]. TETRAHEDRON LETTERS, 1991, 32 (20) : 2253 - 2254
  • [4] MODEL STUDIES DIRECTED TOWARDS MICROALGAL POLYETHER TOXINS - USE OF 2-PHENYL-SULFONYL CYCLIC ETHERS IN THE PREPARATION OF TRANS, SYN, TRANS ALPHA-ALKYL, BETA-HYDROXY-SUBSTITUTED TETRAHYDROPYRAN SUBUNITS
    ALVAREZ, E
    RICO, M
    RODRIGUEZ, RM
    ZURITA, D
    MARTIN, JD
    [J]. TETRAHEDRON LETTERS, 1992, 33 (23) : 3385 - 3388
  • [5] MODEL STUDIES DIRECTED TOWARDS MICROALGA POLYETHER TOXINS - A STEREOSELECTIVE ENTRY INTO C8 OXEPANE SUBUNITS
    ALVAREZ, E
    DIAZ, MT
    PEREZ, R
    MARTIN, JD
    [J]. TETRAHEDRON LETTERS, 1991, 32 (20) : 2241 - 2244
  • [6] MODEL STUDIES DIRECTED TOWARDS MICROALGA POLYETHER TOXINS - A STEREOSELECTIVE ENTRY INTO C10 CIS-FUSED AND TRANS-FUSED OXANE-OXEPANE SUBUNITS
    ALVAREZ, E
    ZURITA, D
    MARTIN, JD
    [J]. TETRAHEDRON LETTERS, 1991, 32 (20) : 2245 - 2248
  • [7] 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
  • [8] ULTRASONICS IN ORGANOBORANE CHEMISTRY - A NOVEL AND POWERFUL METHOD FOR RAPID HYDROBORATION
    BROWN, HC
    RACHERLA, US
    [J]. TETRAHEDRON LETTERS, 1985, 26 (18) : 2187 - 2190
  • [9] SYNTHESIS OF THE SPIROKETAL FRAGMENT OF AVERMECTIN-B1B
    CRIMMINS, MT
    OMAHONY, R
    [J]. TETRAHEDRON LETTERS, 1989, 30 (44) : 5993 - 5996
  • [10] A USEFUL 12-I-5 TRIACETOXYPERIODINANE (THE DESS-MARTIN PERIODINANE) FOR THE SELECTIVE OXIDATION OF PRIMARY OR SECONDARY ALCOHOLS AND A VARIETY OF RELATED 12-I-5 SPECIES
    DESS, DB
    MARTIN, JC
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (19) : 7277 - 7287