ABSOLUTE STEREOCHEMISTRY OF AMPHIDINOLIDE-B

被引:44
作者
ISHIBASHI, M [1 ]
ISHIYAMA, H [1 ]
KOBAYASHI, J [1 ]
机构
[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,SAPPORO,HOKKAIDO 060,JAPAN
关键词
D O I
10.1016/0040-4039(94)88292-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The absolute stereochemistry of amphidinolide B (1), a potent cytotoxic 26-membered macrolide isolated from the cultured marine dinoflagellate Amphidinium sp., has been established as 8S, 9S, 11R, 16R, 18S, 21R, 22S, 23R, and 25S, on the basis of enantiospecific synthesis of a degradation product (2).
引用
收藏
页码:8241 / 8242
页数:2
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共 6 条
  • [1] THE STRUCTURES OF AMPHIDINOLIDE-B ISOMERS - STRONGLY CYTOTOXIC MACROLIDES PRODUCED BY A FREE-SWIMMING DINOFLAGELLATE, AMPHIDINIUM SP
    BAUER, I
    MARANDA, L
    SHIMIZU, Y
    PETERSON, RW
    CORNELL, L
    STEINER, JR
    CLARDY, J
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) : 2657 - 2658
  • [2] SYNTHESIS OF THE C5-C9 FRAGMENT OF THE POLYPROPIONATE UNIT OF THE GEODIAMOLIDES AND JASPAMIDE
    CHIARELLO, J
    JOULLIE, MM
    [J]. SYNTHETIC COMMUNICATIONS, 1989, 19 (19) : 3379 - 3383
  • [3] EFFICIENT SYNTHESES OF GEODIAMOLIDE-A AND JASPAMIDE, CYTOTOXIC AND ANTIFUNGAL CYCLIC DEPSIPEPTIDES OF MARINE SPONGE ORIGIN
    IMAEDA, T
    HAMADA, Y
    SHIOIRI, T
    [J]. TETRAHEDRON LETTERS, 1994, 35 (04) : 591 - 594
  • [4] AMPHIDINOLIDE-B, A NOVEL MACROLIDE WITH POTENT ANTINEOPLASTIC ACTIVITY FROM THE MARINE DINOFLAGELLATE AMPHIDINIUM SP
    ISHIBASHI, M
    OHIZUMI, Y
    HAMASHIMA, M
    NAKAMURA, H
    HIRATA, Y
    SASAKI, T
    KOBAYASHI, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (14) : 1127 - 1129
  • [5] CYTO-TOXIC MACROLIDES FROM A CULTURED MARINE DINOFLAGELLATE OF THE GENUS AMPHIDINIUM
    KOBAYASHI, J
    ISHIBASHI, M
    NAKAMURA, H
    OHIZUMI, Y
    YAMASU, T
    HIRATA, Y
    SASAKI, T
    OHTA, T
    NOZOE, S
    [J]. JOURNAL OF NATURAL PRODUCTS, 1989, 52 (05): : 1036 - 1041
  • [6] AMPHIDINOLIDE-L, A NEW CYTOTOXIC 27-MEMBERED MACROLIDE FROM THE CULTURED DINOFLAGELLATE AMPHIDINIUM SP
    TSUDA, M
    SASAKI, T
    KOBAYASHI, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (13) : 3734 - 3737