Stereoselective 6-exo Radical Cyclization Using cis-Vinyl Sulfoxide: Practical Total Synthesis of CTX3C

Ciguatoxins, the principal causative toxins of ciguatera seafood poisoning, are large ladder-like polycyclic ethers. We report a highly stereoselective 6-exo radical cyclization/ring-closing olefin metathesis sequence to construct the syn/trans-fused polyether system. The new method was applied to t...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 2011-03, Vol.74 (3), p.357-364
Hauptverfasser:	Yamashita, Shuji, Ishihara, Yuuki, Morita, Hiroyuki, Uchiyama, Junichi, Takeuchi, Katsutoshi, Inoue, Masayuki, Hirama, Masahiro
Format:	Artikel
Sprache:	eng
Schlagworte:	Animal poisons toxicology. Antivenoms Biological and medical sciences Chemistry Ciguatera Poisoning - etiology Ciguatoxins - chemical synthesis Ciguatoxins - chemistry Ciguatoxins - pharmacology Cyclization Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Medical sciences Models, Molecular Molecular Structure Organic chemistry Preparations and properties Seafood - poisoning Stereoisomerism Structure-Activity Relationship Sulfoxides - chemistry Toxicology Vinyl Compounds - chemistry
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	Ciguatoxins, the principal causative toxins of ciguatera seafood poisoning, are large ladder-like polycyclic ethers. We report a highly stereoselective 6-exo radical cyclization/ring-closing olefin metathesis sequence to construct the syn/trans-fused polyether system. The new method was applied to the practical synthesis of ciguatoxin CTX3C.
ISSN:	0163-3864 1520-6025
DOI:	10.1021/np100729d