隣接位に酸素官能基を有するビシナルジブロミドの脱離反応を利用した生物活性天然物の全合成研究 Synthetic Studies on Bioactive Natural Products Utilizing the Elimination Reaction of 1,2-Dibromides Possessing Oxygen-Functional Groups at Adjacent Positions

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2-Bromo-1-alkenes have been recognized as one of useful functional groups for preparation of vinyl lithiums and vinyl Grignard reagents, for coupling partners in a wide range of transition metal-mediated coupling reactions, substrates of radical reactions, and precursors of a-haloke-tones. Selective elimination reaction of 1, 2-dibromoalkanes possessing aryloxy or acyloxy groups at the C 3 position into 2-bromo-1-alkenes under mild basic conditions was developed. Alkyne units are also one of the important functional groups for substrates of C-C coupling reactions. During our extensive investigation, the acidity enhancement of hydrogen at the C 1 position by oxygen-functional groups at the C 3 position was also observed. This observation indicated a new prospective synthesis of propargyl ethers from 1, 2-dibromoalkanes using DBU as a base. As application of these elimination reactions, total synthesis of biologically active natural products was accomplished.

収録刊行物

  • 有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN  

    有機合成化学協会誌 : JOURNAL OF Synthetic Organic Chemistry JAPAN 66(2), 139-147, 2008-02-01 

    The Society of Synthetic Organic Chemistry, Japan

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各種コード

  • NII論文ID(NAID)
    10021173642
  • 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
    9379016
  • 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  NDL  J-STAGE 
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