Synthesis and Biological Activity of the QRS Ring System of Maitotoxin

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Author(s)

    • Onoue Hisaaki
    • Department of Chemistry, Faculty and Graduate School of Sciences, Kyushu University
    • Baba Tomomi
    • Department of Chemistry, Faculty and Graduate School of Sciences, Kyushu University
    • Torikai Kohei
    • Department of Chemistry, Faculty and Graduate School of Sciences, Kyushu University
    • Ebine Makoto
    • Department of Chemistry, Faculty and Graduate School of Sciences, Kyushu University
    • Oishi Tohru
    • Department of Chemistry, Faculty and Graduate School of Sciences, Kyushu University

Abstract

Maitotoxin (MTX) is a ladder-shaped polyether produced by an epiphytic dinoflagellate. As a part of our structure–activity relationship studies using synthetic partial structures of MTX, the QRS ring comprising a 6/6/7 tricyclic system was synthesized through stereoselective construction of five contiguous stereogenic centers on the Q ring via i) coupling of a Weinreb amide and a furyllithium, followed by ii) Noyori asymmetric transfer hydrogenation, iii) the Achmatowicz reaction, iv) chemoselective methylation of a methyl acetal in the presence of a carbonyl group by treatment with Me<sub>2</sub>Zn/BF<sub>3</sub>·OEt<sub>2</sub>, v) highly diastereoselective dihydroxylation, and vi) ring expansion of a six-membered to a seven-membered ring ketone. The synthetic specimen inhibited MTX-induced Ca<sup>2+</sup> influx with an IC<sub>50</sub> value of 44 µM.

Journal

  • Chemistry Letters

    Chemistry Letters 43(12), 1904-1906, 2014

    The Chemical Society of Japan

Codes

  • NII Article ID (NAID)
    130004690780
  • Text Lang
    ENG
  • ISSN
    0366-7022
  • Data Source
    J-STAGE 
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