エポラクタエンの不斉全合成  [in Japanese] Asymmetric Total Synthesis of Epolactaene  [in Japanese]

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Author(s)

Abstract

A total synthesis of the neuritegenic agent, epolactaene has been achieved via a convergent approach in 14 steps from optically active lactaldehyde derivatives. The key steps include (i) the stereoselective aldol reaction between malonate ester enolate and α-alkoxy aldehyde (ii) diastereospecific lactonization of malonate ester (iii) <I>E</I>-selective Wittig reaction. The optical rotation was identical with that of the natural (+) -epolactaene, which establishes that the absolute configuration of natural (+) -epolactaene is (13<I>R</I>, 14<I>R</I>) definitively. Other several epoxy-γ-lactam compounds also synthesized which suggest this method would be general for organic synthesis.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 58(3), 183-191, 2000-03-01

    The Society of Synthetic Organic Chemistry, Japan

References:  56

Codes

  • NII Article ID (NAID)
    10008819273
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    ART
  • ISSN
    00379980
  • NDL Article ID
    5301703
  • 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  NDL  J-STAGE 
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