Synthesis of the EF-ring of ciguatoxin 3C based on the [2,3]-Wittig rearrangement and ring-closing olefin metathesis.
The EF-ring segment of ciguatoxin 3C, a causative toxin of ciguatera fish poisoning, was synthesized in three major steps: 1,4-addition for the C20O-C27 bond connection, chirality transferring anti selective [2,3]-Wittig rearrangement for the construction of the anti-2-hydroxyalkyl ether part, and ring-closing olefin metathesis for the F-ring formation.
Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo 060-0810, Japan.
Akiyoshi
A
Goto
Kenshu
K
Fujiwara
Ayako
A
Kawai
Hidetoshi
H
Kawai
Takanori
T
Suzuki
D000475:Alkenes / Q000737:chemistry*; D002922:Ciguatoxins / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization
D000475:Alkenes; C466858:ciguatoxin 3C; D002922:Ciguatoxins