アセチレンコバルト錯体を利用した化学合成(2)  [in Japanese] New Synthesis with Acetylene Biscobalthexacarbonyl Complex(2)  [in Japanese]

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Author(s)

    • 磯部 稔 ISOBE Minoru
    • 名古屋大学大学院生命農学研究科 Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya University
    • 吉良 和信 KIRA Kazunobu
    • 名古屋大学大学院生命農学研究科 Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya University

Abstract

Following our previous review of this issue, chemistry of acetylene biscobalthexacarbonyl complex is discussed with special reference in the synthesis of natural and unnatural products. The first example is to do with protein phosphatase inhibitors; thus, okadaic acid and tautomycin are known as strong inhibitors to these enzymes with high specificity of the enzyme type. Hybrid molecules are discussed as unnatural product having enantiomeric spiro moieties. These syntheses have been achieved via enantio-switching method from the same D-glucose derivatives; namely, alkynylation of silylacetylene to sugars provides sugar acetylenes, which are convertible with or without epimerization into α or β heteroolefins leading to enantiomer to each other. Heteroconjugate addition on pyranose ring can provide either <I>syn</I> or anti adduct by switching the chelational anchor and metals of the nucleophile. Pauson-Khand reaction is demonstrated on the sugar acetylenes to provide tricyclic compounds with definite stereoisomer. A macrocyclic ring closure is a specific example of the cobalt complex with C-C bond formation in the critical step. Cobalt chemistry and sugar acetylene chemistry made it possible to provide both of the enantiomers of left end segments of ciguatoxin. This line also discussed to the potential methodology directed toward other portion of this marine natural toxin. These endo-cyclic complexes have reductively been decomplexed into the olefins or vinylsilanes.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 58(2), 99-107, 2000-02-01

    The Society of Synthetic Organic Chemistry, Japan

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Codes

  • NII Article ID (NAID)
    10008818928
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    Journal Article
  • ISSN
    00379980
  • NDL Article ID
    4987394
  • NDL Source Classification
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL Call No.
    Z17-256
  • Data Source
    CJP  CJPref  NDL  J-STAGE 
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