Synthesis and Biological Activity of the C′D′E′F′ Ring System of Maitotoxin

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