Facile Synthesis of β-Hydroxy-γ-Varelolactone via the Ring Opening Reaction of β-Trichloromethyl-β-Propiolactone with Ester Enolates

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抄録

The reaction of enantiomerically pure (<I>S</I>)-β-trichloromethyl-β-propiolactone with enolate derived from <I>t</I>-butyl acetate gave δ-hydroxy-β-ketoester in good yield. Subsequent <I>syn</I>-selective reduction of ketone and cyclization gave β-hydroxy-γ-varelolactones in good yield in enantiomerically pure form. The β-hydroxy-γ-varelolactones thus obtained are excellent precursors for the synthesis of compactin and mevinolin derivatives of potent inhibitor of hydroxymethylglutaryl coenzyme A reductase (HMG CoA reductase).

収録刊行物

  • Chemistry letters

    Chemistry letters 1997(8), 765-766, 1997-08

    The Chemical Society of Japan

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各種コード

  • NII論文ID(NAID)
    10002613875
  • NII書誌ID(NCID)
    AA00603318
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    03667022
  • データ提供元
    CJP書誌  J-STAGE 
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