[Updated on Apr. 18] Integration of CiNii Articles into CiNii Research

Total Synthesis and Structure–Activity Relationship Studies of Phelligridins C and D, and Phellifuropyranone A

  • Ohyoshi Takayuki
    Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Mitsugi Keisuke
    Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Ichimura Fumitaka
    Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Higuma Tatsuya
    Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Yoshida Masahito
    Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba
  • Kigoshi Hideo
    Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba

Abstract

<p>α-Pyrone polyphenols, phelligridins C and D (meshimakobnols B and A), and phellifuropyranone A, isolated from a Japanese mushroom, are growth inhibitors of cancer cells. Herein, we report full details of the total synthesis of phelligridins C and D. The key reactions of the synthetic pathways were Pd catalyzed cross-coupling and aldol-type condensation. This strategy also enabled the total synthesis of phellifuropyranone A and artificial analogs of phelligridins. Subsequent biological evaluation of these compounds clarified that the whole skeleton of phelligridin C and the catechol group of the left hand side are essential for the cytotoxicity.</p>

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