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

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...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2014-06, Vol.79 (11), p.4948-4962
Main Authors: Kunitake, Masahiro, Oshima, Takahiro, Konoki, Keiichi, Ebine, Makoto, Torikai, Kohei, Murata, Michio, Oishi, Tohru
Format: Article
Language:English
Subjects:
Animals
Catalysis
Cyclization
Inhibitory Concentration 50
Marine Toxins - antagonists & inhibitors
Marine Toxins - chemical synthesis
Marine Toxins - chemistry
Molecular Structure
Oxocins - antagonists & inhibitors
Oxocins - chemical synthesis
Oxocins - chemistry
Palladium - chemistry
Polycyclic Compounds - chemical synthesis
Polycyclic Compounds - chemistry
Propanols - chemistry
Rats
Stereoisomerism
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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.
ISSN:1520-6904
DOI:10.1021/jo5005235