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

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著者

    • 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

抄録

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.

収録刊行物

  • 有機合成化学協会誌

    有機合成化学協会誌 58(2), 99-107, 2000-02-01

    The Society of Synthetic Organic Chemistry, Japan

参考文献:  54件中 1-54件 を表示

  • <no title>

    磯部稔

    有合化 58, 23, 2000

    被引用文献2件

  • <no title>

    CHENG X. -C.

    J. Antibit. 40, 907, 1987

    被引用文献1件

  • <no title>

    MAGAE J.

    J. Antibit. 41, 932, 1988

    被引用文献1件

  • <no title>

    MAGAE J.

    Proc. Japan Acad., Ser. B 66, 209, 1900

    被引用文献1件

  • <no title>

    UBUKATA M.

    J. Chem. Soc., Chem. Commun. 1990, 244

    被引用文献2件

  • <no title>

    CHENG X. -C.

    J. Antibit. 43, 809, 1990

    被引用文献1件

  • <no title>

    UBUKATA M.

    J. Chem. Soc., Perkin Trans. 1, 617, 1993

    被引用文献1件

  • <no title>

    ISOBE M.

    Tetrahedron Lett. 27, 963, 1986

    被引用文献6件

  • <no title>

    ISOBE M.

    Tetrahedron 42, 2863, 1986

    被引用文献2件

  • <no title>

    ISOBE M.

    Tetrahedron 43, 4767, 1987

    被引用文献4件

  • <no title>

    OIKAWA H.

    Tetrahedron Lett. 35, 4809, 1994

    被引用文献2件

  • <no title>

    ICHIKAWA Y.

    Tetrahedron Lett. 36, 7101, 1995

    被引用文献2件

  • <no title>

    JIANG Y.

    Synlett 1995, 285

    被引用文献2件

  • <no title>

    JIANG Y.

    Tetrahedron 53, 5103, 1997

    被引用文献1件

  • <no title>

    ISOBE M.

    Tetrahedron Lett. 1979, 3465

    被引用文献2件

  • <no title>

    ISOBE M.

    Tetrahedron Lett. 25, 2021, 1984

    被引用文献2件

  • New Synthetic Methods Using Vinyl Sulfones-Developments in Heteroconjugate Addition

    ZWANENBURG B.

    Perspectives in the Organic Chemistry of Sulfur : Studies in Organic Chemistry 28, 209, 1987

    被引用文献1件

  • <no title>

    磯部稔

    有合化 55, 44, 1997

    被引用文献1件

  • <no title>

    TSUBOI K.

    Synlett 1997, 713

    被引用文献1件

  • <no title>

    KHAND I. U.

    J. Chem. Soc., Perkin Trans. 1, 975, 1973

    被引用文献2件

  • <no title>

    KHAND I. U.

    J. Chem. Soc., Perkin Trans. 1, 977, 1973

    被引用文献1件

  • <no title>

    PAUSON P. L.

    Organometallics in Organic Synthesis 233, 1987

    被引用文献1件

  • <no title>

    SHORE N. E.

    Comprehensive Organic Synthesis 5, 1037, 1991

    被引用文献4件

  • <no title>

    SHORE N. E.

    Comprehensive Organometallic Chemistry II 703, 1995

    被引用文献1件

  • <no title>

    杉原多公通

    有合化 57, 158, 1999

    被引用文献1件

  • <no title>

    WANI M. C.

    J.Am.Chem.Soc. 93, 2325, 1971

    被引用文献8件

  • <no title>

    HOLTON R. A.

    J. Am. Chem. Soc. 116, 1599, 1994

    被引用文献8件

  • <no title>

    K. C. Nicolaou group

    Nature 367, 630, 1994

    被引用文献1件

  • <no title>

    S. J. Danishefsky group

    Angew. Chem., Int. Ed. Engl. 34, 1723, 1995

    被引用文献1件

  • <no title>

    P. A. Wender group

    J. Am. Chem. Soc. 119, 2757, 1997

    被引用文献1件

  • <no title>

    T. Mukaiyama group

    Proc. Japan Acad. 73, Ser B, 95, 1997

    被引用文献1件

  • <no title>

    I. Kuwajima group

    J. Am. Chem. Soc. 120, 12980, 1998

    被引用文献1件

  • <no title>

    JAMISON T. F.

    J. Am. Chem. Soc. 119, 4353, 1997

    被引用文献3件

  • <no title>

    SHIBUYA S.

    Tetrahedron 54, 6677, 1998

    被引用文献1件

  • <no title>

    ALVAREZ E.

    Tetrahedron Lett. 37, 2865, 1996

    被引用文献3件

  • <no title>

    OKA T.

    Tetrahedron 54, 21, 1998

    被引用文献5件

  • <no title>

    OISHI T.

    Chem. Commun. 1998, 1041

    被引用文献3件

  • <no title>

    MAEDA K.

    Chem. Commun. 1999, 1063

    被引用文献4件

  • <no title>

    SASAKI M.

    Org. Lett. 1, 1075, 1999

    被引用文献7件

  • <no title>

    INOUE M.

    Tetrahedron 55, 10949, 1999

    被引用文献4件

  • <no title>

    HOSOKAWA S.

    Synlett 1995, 1179

    被引用文献8件

  • <no title>

    HOSOKAWA S.

    Synlett 1996, 351

    被引用文献7件

  • <no title>

    HOSOKAWA S.

    J. Org. Chem. 65, 37, 1999

    被引用文献1件

  • <no title>

    SAEENG R.

    Tetrahedron Lett. 40, 1911, 1999

    被引用文献4件

  • <no title>

    MAGNUS P.

    J. Am. Chem. Soc. 110, 1626, 1988

    被引用文献1件

  • <no title>

    MAGNUS P.

    J. Am. Chem. Soc. 110, 6921, 1988

    被引用文献1件

  • <no title>

    NAGASAWA T.

    J. Am. Chem. Soc. 118, 8949, 1996

    被引用文献3件

  • <no title>

    ISOBE M.

    J. Am. Chem. Soc. 104, 4997, 1982

    被引用文献3件

  • <no title>

    NISHIKAWA T.

    Angew. Chem., Int. Ed. Engl. 38, 3081, 1999

    被引用文献1件

  • <no title>

    SHIMIZU S.

    Tetrahedron 52, 13363, 1996

    DOI 被引用文献1件

  • <no title>

    SHEPPECK J. E.

    J. Org. Chem. 62, 387, 1997

    DOI 被引用文献1件

  • <no title>

    ISOBE M.

    J. Organomet. Chem. 589/1, 122, 1999

    DOI 被引用文献1件

  • <no title>

    SATAKE M.

    J. Am. Chem. Soc. 119, 11325, 1997

    DOI 被引用文献20件

  • <no title>

    OKA T.

    Tetrahedron 54, 1, 1998

    DOI 被引用文献4件

被引用文献:  2件中 1-2件 を表示

各種コード

  • NII論文ID(NAID)
    10008818928
  • NII書誌ID(NCID)
    AN0024521X
  • 本文言語コード
    JPN
  • 資料種別
    ART
  • ISSN
    00379980
  • NDL 記事登録ID
    4987394
  • NDL 雑誌分類
    ZP11(科学技術--化学・化学工業--有機化学・有機化学工業)
  • NDL 請求記号
    Z17-256
  • データ提供元
    CJP書誌  CJP引用  NDL  J-STAGE 
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