Convergent Synthesis of the WXYZA′B′C′D′E′F′ Ring Segment of Maitotoxin

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  • Keitaro Umeno
    Deparrtment of Chemistry, Faculty and Graduate School of Science, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 , Japan
  • Hisaaki Onoue
    Deparrtment of Chemistry, Faculty and Graduate School of Science, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 , Japan
  • Keiichi Konoki
    Graduate School of Agricultural Science, Tohoku University, 468-1 Aramaki Aza-Aoba, Aoba-ku, Sendai, Miyagi 980-8572 , Japan
  • Kohei Torikai
    Deparrtment of Chemistry, Faculty and Graduate School of Science, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 , Japan
  • Yoko Yasuno
    Deparrtment of Chemistry, Faculty and Graduate School of Science, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 , Japan
  • Masayuki Satake
    Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 , Japan
  • Tohru Oishi
    Deparrtment of Chemistry, Faculty and Graduate School of Science, Kyushu University, 744 Motooka, Nishi-ku, Fukuoka 819-0395 , Japan

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<jats:title>Abstract</jats:title> <jats:p>Synthesis of the WXYZA′B′C′D′E′F′ ring segment of maitotoxin, a ladder-shaped polyether produced by the dinoflagellate Gambierdiscus toxicus, was achieved based on a convergent strategy via α-cyano ethers developed in our laboratory. The WXYZ ring aldehyde and the C′D′E′F′ diol were combined through the construction of the B′ ring via ring-closing metathesis and the A′ ring via O,S-acetal formation followed by radical reduction. Introduction of a terminal olefin in the side chain culminated in the convergent synthesis of the WXYZA′B′C′D′E′F′ ring segment in 16 steps.</jats:p>

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