Synthesis and Biological Activity of the QRS Ring System of Maitotoxin

• 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

• Konoki Keiichi

  Graduate School of Agricultural Science, Tohoku 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

抄録

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 Me₂Zn/BF₃·OEt₂, v) highly diastereoselective dihydroxylation, and vi) ring expansion of a six-membered to a seven-membered ring ketone. The synthetic specimen inhibited MTX-induced Ca²⁺ influx with an IC₅₀ value of 44 µM.

収録刊行物

• Chemistry Letters

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

  公益社団法人 日本化学会

キーワード

• General Chemistry

詳細情報

• CRID: 1390001204587232512
• NII論文ID: 130004690780
• DOI: 10.1246/cl.140789
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/43/12/1904/55636982/cl.140789.pdf
• 本文言語コード: en
• データソース種別:
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  • Crossref
  • CiNii Articles
  • KAKEN
• 抄録ライセンスフラグ: 使用不可