Practical Total Synthesis of Ciguatoxin CTX3C by Improved Protective Group Strategy

Practical Total Synthesis of Ciguatoxin CTX3C by Improved Protective Group Strategy

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. Alte...

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Veröffentlicht in:Organic letters 2002-12, Vol.4 (25), p.4551-4554
Hauptverfasser: Inoue, Masayuki, Uehara, Hisatoshi, Maruyama, Megumi, Hirama, Masahiro
Format: Artikel
Sprache:eng
Schlagworte:
Ciguatera Poisoning
Ciguatoxins - chemical synthesis
Ciguatoxins - chemistry
Molecular Structure
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol027105m