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

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4948-4962
Number of pages15
JournalJournal of Organic Chemistry
Volume79
Issue number11
DOIs
Publication statusPublished - Jun 6 2014

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Cyclization
Bioactivity
Rats
maitotoxin
allyl alcohol

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Cite this

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.

In: Journal of Organic Chemistry, Vol. 79, No. 11, 06.06.2014, p. 4948-4962.

Research output: Contribution to journalArticle

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. In: Journal of Organic Chemistry. 2014 ; Vol. 79, No. 11. pp. 4948-4962.
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