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

doi:10.1021/jo5005235

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

Organic and Biological Chemistry

Research output: Contribution to journal › Article › peer-review

19 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 language	English
Pages (from-to)	4948-4962
Number of pages	15
Journal	Journal of Organic Chemistry
Volume	79
Issue number	11
DOIs	https://doi.org/10.1021/jo5005235
Publication status	Published - Jun 6 2014

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1021/jo5005235

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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.",

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AU - Kunitake, Masahiro

AU - Oshima, Takahiro

AU - Konoki, Keiichi

AU - Ebine, Makoto

AU - Torikai, Kohei

AU - Murata, Michio

AU - Oishi, Tohru

PY - 2014/6/6

Y1 - 2014/6/6

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AB - 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.

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

Abstract

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