Pinnatoxin A の全合成  [in Japanese] Total Synthesis of Pinnatoxin A  [in Japanese]

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Abstract

The first total synthesis of pinnatoxin A (1), a Ca<SUP>2+</SUP>-channel activator isolated in 1995 by Uemura and co-workers from the shellfish <I>Pinna muricata</I>, is reported. The synthetic plan was based on Uemura's biosynthetic proposal, and consists of an intramolecular Diels-Alder reaction for construction of the G-ring as well as the macrocycle, followed by imine formation to establish the 6, 7-spiro-ring system. During this investigation, factors controlling the stereochemistry of the BCD bis-spiroketal ring system were investigated, and the chemoselectivity and efficiency of the Ni (II) /Cr (II) -mediated coupling protocol were demonstrated. This synthesis has also established the absolute stereochemistry of natural pinnatoxin A as the antipode of structure 1.

Journal

  • Journal of Synthetic Organic Chemistry, Japan

    Journal of Synthetic Organic Chemistry, Japan 58(9), 877-886, 2000-09-01

    The Society of Synthetic Organic Chemistry, Japan

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Codes

  • NII Article ID (NAID)
    10008821884
  • NII NACSIS-CAT ID (NCID)
    AN0024521X
  • Text Lang
    JPN
  • Article Type
    REV
  • ISSN
    00379980
  • NDL Article ID
    5474971
  • 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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