Total Synthesis and Biological Evaluation of Auripyrones A and B

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Author(s)

    • Hayakawa Ichiro
    • Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba
    • Takemura Takuma
    • Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba|Japan Society for the Promotion of Science (JSPS)
    • Fukasawa Emi
    • Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba
    • Ebihara Yuta
    • Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba
    • Sato Natsuki
    • Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba
    • Nakamura Takayasu
    • Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba
    • Suenaga Kiyotake
    • 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

The total synthesis of auripyrones was achieved by using a novel aldol-type reaction of γ-pyrone as a key step. From this synthetic work, we have established the stereostructure and absolute configuration of auripyrone B. Furthermore, the cytotoxicities of auripyrones against a panel of 39 human cancer cell lines (termed JFCR39) at the Japanese Foundation for Cancer Research were investigated. The patterns of the differential cytotoxicities of auripyrones were COMPARE negative, suggesting that they inhibit cancer cell proliferation through a novel mechanism.

Journal

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 85(10), 1077-1092, 2012

    The Chemical Society of Japan

Codes

  • NII Article ID (NAID)
    130004152992
  • Text Lang
    ENG
  • ISSN
    0009-2673
  • Data Source
    J-STAGE 
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