Synthesis and biological activity of the C'D'E'F' ring system of maitotoxin

Masahiro Kunitake, Takahiro Oshima, Keiichi Konoki, Makoto Ebine, Kohei Torikai, Michio Murata, Tohru Oishi

研究成果: ジャーナルへの寄稿記事

11 引用 (Scopus)

抄録

Stereoselective synthesis of the C'D'E'F' ring system of maitotoxin was achieved starting from the E' ring through successive formation of the D' and C' rings based on SmI2-mediated reductive cyclization. Construction of the F' ring was accomplished via Suzuki-Miyaura cross-coupling with a side chain fragment and Pd(II)-catalyzed cyclization of an allylic alcohol. The C'D'E'F' ring system inhibited maitotoxin-induced Ca2+ influx in rat glioma C6 cells with an IC50 value of 59 μM.

元の言語英語
ページ(範囲)4948-4962
ページ数15
ジャーナルJournal of Organic Chemistry
79
発行部数11
DOI
出版物ステータス出版済み - 6 6 2014

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Cyclization
Bioactivity
Rats
maitotoxin
allyl alcohol

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

これを引用

Synthesis and biological activity of the C'D'E'F' ring system of maitotoxin. / Kunitake, Masahiro; Oshima, Takahiro; Konoki, Keiichi; Ebine, Makoto; Torikai, Kohei; Murata, Michio; Oishi, Tohru.

:: Journal of Organic Chemistry, 巻 79, 番号 11, 06.06.2014, p. 4948-4962.

研究成果: ジャーナルへの寄稿記事

Kunitake, Masahiro ; Oshima, Takahiro ; Konoki, Keiichi ; Ebine, Makoto ; Torikai, Kohei ; Murata, Michio ; Oishi, Tohru. / Synthesis and biological activity of the C'D'E'F' ring system of maitotoxin. :: Journal of Organic Chemistry. 2014 ; 巻 79, 番号 11. pp. 4948-4962.
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AU - Murata, Michio

AU - Oishi, Tohru

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