Synthesis and Biological Activity of the QRS Ring System of Maitotoxin
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概要
- 論文の詳細を見る
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 comprised of a 6/6/7 tricyclic system was synthesized through stereoselective construction of the 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) 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.
- 公益社団法人 日本化学会の論文
著者
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Oishi Tohru
Department Of Chemistry Graduate School Of Science Osaka University
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Torikai Kohei
Department Of Chemistry Graduate School Of Science Osaka University
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Ebine Makoto
Department Of Chemistry Graduate School Of Sciences Kyushu University
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Ebine Makoto
Department of Chemistry, Faculty and Graduate School of Sciences, Kyushu University
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Onoue Hisaaki
Department of Chemistry, Faculty and Graduate School of Sciences, Kyushu University
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Baba Tomomi
Department of Chemistry, Faculty and Graduate School of Sciences, Kyushu University
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Konoki Keiichi
Graduate School of Agricultural Science, Tohoku University
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