Total synthesis of (6S,1'S,2'R)-6-(1',2'-dihydroxypentyl)-4-methoxy-5,6-dihydropyrane-2-one (LL-P880.BETA.) and its C6-epimer, a fungal metabolite from Penicillium sp.

DOI 1 Citations
  • KIRIHATA Mitsunori
    Department of Agricultural Chemistry, College of Agriculture, University of Osaka Prefecture
  • OHTA Kazunari
    Department of Agricultural Chemistry, College of Agriculture, University of Osaka Prefecture Present address: Plant Protection Research Laboratory of Agro Division, Takeda Pharmaceutical Co.
  • ICHIMOTO Itsuo
    Department of Agricultural Chemistry, College of Agriculture, University of Osaka Prefecture
  • UEDA Hiroo
    Department of Agricultural Chemistry, College of Agriculture, University of Osaka Prefecture

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Abstract

A fungal metabolite, (6S, 1'S, 2'R)-6-(1', 2'-dihydroxypentyl)-4-methoxy-5, 6-dihydropyrane-2-one (LL-P88β, I), and its C6-epimer (II) were synthesized by the chiron approach. The key intermediate, (2S, 3R)-2, 3-dihydroxyhexanal derivative (3), was prepared from D-glucose as a chiral building block and reacted with the dianion of ethyl acetoacetate to complete the formal syntheses of I and II.

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Details 詳細情報について

  • CRID
    1390282681437310720
  • NII Article ID
    110006325137
  • NII Book ID
    AA00515312
  • DOI
    10.1271/bbb1961.54.2401
  • ISSN
    18811280
    00021369
  • Text Lang
    en
  • Data Source
    • JaLC
    • Crossref
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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