Practical total synthesis of ciguatoxin CTX3C by improved protective group strategy.
[structure: see text] Ciguatoxin CTX3C is a representative congener of ciguatoxins, which are known to be the principal causative agents of ciguatera seafood poisoning. The structure of CTX3C spans more than 3 nm and is characterized by 13 ether rings. In this paper, an improved total synthesis of CTX3C is reported. Alteration of the protective group from benzyl ether to 2-naphthylmethyl (NAP) ether drastically increases the yield for final global deprotection and has provided a sufficient amount of sample for further biological studies.
Inoue
Masayuki
M
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.
Uehara
Hisatoshi
H
Maruyama
Megumi
M
Hirama
Masahiro
M
D036841:Ciguatera Poisoning; D002922:Ciguatoxins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
C466858:ciguatoxin 3C; D002922:Ciguatoxins