title: 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 Ca(2+) influx in rat glioma C6 cells with an IC50 value of 59 μM.
authors.affiliation: Department of Chemistry, Faculty and Graduate School of Sciences, Kyushu University , 6-10-1 Hakozaki, Higashi-ku, Fukuoka 812-8581, Japan.
authors.forename: Masahiro
authors.initials: M
authors.lastname: Kunitake
authors.forename: Takahiro
authors.initials: T
authors.lastname: Oshima
authors.forename: Keiichi
authors.initials: K
authors.lastname: Konoki
authors.forename: Makoto
authors.initials: M
authors.lastname: Ebine
authors.forename: Kohei
authors.initials: K
authors.lastname: Torikai
authors.forename: Michio
authors.initials: M
authors.lastname: Murata
authors.forename: Tohru
authors.initials: T
authors.lastname: Oishi
mesh_terms: D000818:Animals; D002384:Catalysis; D003500:Cyclization; D020128:Inhibitory Concentration 50; D008387:Marine Toxins / Q000037:antagonists & inhibitors* / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D035964:Oxocins / Q000037:antagonists & inhibitors* / Q000138:chemical synthesis* / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D051381:Rats; D013237:Stereoisomerism; D000095702:Polyether Toxins
chemical_list: D008387:Marine Toxins; D035964:Oxocins; D010165:Palladium; D011083:Polycyclic Compounds; D020005:Propanols; C006463:allyl alcohol; C020394:maitotoxin; D000095702:Polyether Toxins