Regioselective Synthesis of 6-Alkyl- and 6-Prenylpolyhydroxyisoflavones and 6-Alkylcoumaronochromone Derivatives

    • TSUKAYAMA Masao
    • Department of Chemical Science and Technology, Faculty of Engineering, The University of Tokushima
    • WADA Hironari
    • Department of Chemical Science and Technology, Faculty of Engineering, The University of Tokushima
    • KAWAMURA Yasuhiko
    • Department of Chemical Science and Technology, Faculty of Engineering, The University of Tokushima
    • YAMASHITA Kazuyo
    • Department of Chemical Science and Technology, Faculty of Engineering, The University of Tokushima
    • NISHIUCHI Masaki
    • Department of Chemical Science and Technology, Faculty of Engineering, The University of Tokushima

Abstract

The palladium-catalyzed coupling reaction of 6-iodoisoflavone, prepared from 3'-iodoacetophenone derivative, with 2-methyl-3-butyn-2-ol gave 6-alkynylisoflavone derivative, which was hydrogenated to give 6-alkylhy-droxyisoflavone (luteone hydrate) (2). Dehydration of 2 gave 2', 4', 5, 7-tetrahydroxy-6-prenylisoflavone (luteone) (1). Wighteone hydrate (3) was also synthesized from 6-iodotris(benzyloxy)isoflavone in a similar manner. 6-Alkyl-4'5, 7-trihydroxy-coumaronochromone (4) was synthesized by oxidative cyclization of 2 with o-chloranil.

Journal

Chemical & pharmaceutical bulletin   [List of Volumes]

Chemical & pharmaceutical bulletin 52(11), 1285-1289, 2004-11-01  [Table of Contents]

The Pharmaceutical Society of Japan

References:  23

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Codes

  • NII Article ID (NAID) :
    110003665433
  • NII NACSIS-CAT ID (NCID) :
    AA00602100
  • Text Lang :
    ENG
  • Article Type :
    ART
  • ISSN :
    00092363
  • NDL Article ID :
    7129392
  • NDL Source Classification :
    ZS51(科学技術--薬学) // ZP1(科学技術--化学・化学工業)
  • NDL Call No. :
    Z53-D167
  • DOI :
    10.1248/cpb.52.1285
  • Databases :
    CJP  NDL  NII-ELS  J-STAGE