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 the practical synthesis of ciguatoxin CTX3C.
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. s-yamashita@m.tohoku.ac.jp
Shuji
S
Yamashita
Yuuki
Y
Ishihara
Hiroyuki
H
Morita
Junichi
J
Uchiyama
Katsutoshi
K
Takeuchi
Masayuki
M
Inoue
Masahiro
M
Hirama
D036841:Ciguatera Poisoning / Q000209:etiology*; D002922:Ciguatoxins / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D017747:Seafood / Q000506:poisoning*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013454:Sulfoxides / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
D013454:Sulfoxides; D014753:Vinyl Compounds; C466858:ciguatoxin 3C; D002922:Ciguatoxins