1. Synthesis and Biological Activity of the C'D'E'F' Ring System of Maitotoxin.
- Author
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Masahiro Kunitake, Takahiro Oshima, Keiichi Konoki, Makoto Ebine, Kohei Torikai, Michio Murata, and Tohru Oishi
- Subjects
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STEREOSELECTIVE reactions , *MAITOTOXIN , *RING formation (Chemistry) , *SUZUKI reaction , *ALLYL alcohol , *GLIOMAS , *LABORATORY rats , *GENETICS - 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. [ABSTRACT FROM AUTHOR]
- Published
- 2014
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