Issue 17, 2010
From the journal:

Chemical Communications

The first F-ring modified ciguatoxin analogue showing significant toxicity†

Yuuki Ishihara,a   Nayoung Lee,a   Naomasa Oshiro,b   Shigeru Matsuoka,c   Shuji Yamashita,*a   Masayuki Inouec  and  Masahiro Hirama*ad  

* Corresponding authors

a Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
E-mail: s-yamashita@mail.tains.tohoku.ac.jp, hirama@mail.tains.tohoku.ac.jp
Fax: +82-22-795-6566

b Okinawa Prefectural Institute of Health and Environment, Nanjo 901-1202, Japan

c Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan

d Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan

Abstract

Ciguatoxins, the principal causative toxins of ciguatera seafood poisoning, are potent neurotoxic polycyclic ethers. We report herein the total synthesis of a 10-membered F-ring analogue of 51-hydroxyCTX3C, which constitutes the first example of an F-ring modified ciguatoxin that exhibits potent cytotoxicity as well as mouse acute toxicity.

Graphical abstract: The first F-ring modified ciguatoxin analogue showing significant toxicity

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Article information

DOI
https://doi.org/10.1039/B924375E
Article type
Communication
Submitted
20 Nov 2009
Accepted
12 Feb 2010
First published
05 Mar 2010

Chem. Commun., 2010,46, 2968-2970

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The first F-ring modified ciguatoxin analogue showing significant toxicity

Y. Ishihara, N. Lee, N. Oshiro, S. Matsuoka, S. Yamashita, M. Inoue and M. Hirama, Chem. Commun., 2010, 46, 2968 DOI: 10.1039/B924375E

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