Practical total synthesis of ciguatoxin CTX3C by improved protective group strategy

Masayuki Inoue; Hisatoshi Uehara; Megumi Maruyama; Masahiro Hirama

doi:10.1021/ol027105m

Practical total synthesis of ciguatoxin CTX3C by improved protective group strategy

Org Lett. 2002 Dec 12;4(25):4551-4. doi: 10.1021/ol027105m.

Authors

Masayuki Inoue¹, Hisatoshi Uehara, Megumi Maruyama, Masahiro Hirama

Affiliation

¹ Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan.

PMID: 12465935
DOI: 10.1021/ol027105m

Abstract

[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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Ciguatera Poisoning
Ciguatoxins / chemical synthesis*
Ciguatoxins / chemistry
Molecular Structure

Substances

ciguatoxin 3C
Ciguatoxins