アセチレンコバルト錯体を利用した化学合成(1)  [in Japanese] New Synthesis with Acetylene Biscobalthexacarbonyl Complex(1)  [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生物有機化学研究室 Laboratory of Organic Chemistry, School of Bioagricultural Sciences
    • 吉良 和信 KIRA Kazunobu
    • 名古屋大学大学院生命農学研究科生物有機化学研究室 Laboratory of Organic Chemistry, School of Bioagricultural Sciences

Abstract

Syntheses of multi-functional natural and unnatural compounds have been of great significance in organic chemistry not only as the target molecules but also as leading field for conceptual and methodological developments. Particularly those compounds in relation to biology have collecting attentions from various field such as structure-activity relationship, asymmetric synthesis, drug design for chemotherapy and agricultural control, etc. We have to keep looking for new chemistry for these purposes; thus, we became interesting in the acetylene biscobalthexacarbonyl complex from its synthetic point of views. It started from our previous <I>C</I>-glycosidation with silylacetylenes providing sugar acetylenes, in which the alkynyl group at the anomeric position of a pyranose ring can be epimerized through a biscobalthexacarbonyl complex by treatment with trifluoromethanesulfonic acid. Three steps involving cobalt complexation, acidic transformation and decomplexation afford overall epimerization and thus one can obtain either the α- or β-alkynyl <I>C</I>-glycoside as desired. Ring opening of a dihydropyran derivative using Nicholas-type cation intermediates was also an accomplished part of this study. Several decomplexation conditions of endo-type acetylenecobalt complexes provide various olefins possessing potential utilities for synthesis. These methodologies have been utilized for the synthesis of polyoxygenated natural products and derivatives. Basis of these chemistry is described in this issue, and the application and more examples are to be described in the next issue.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 58(1), 23-30, 2000-01-01

    The Society of Synthetic Organic Chemistry, Japan

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Codes

  • NII Article ID (NAID)
    10008818676
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    Journal Article
  • ISSN
    00379980
  • NDL Article ID
    4957650
  • 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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