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More than 20,000 people suffer annually from ciguatera seafood
poisoning in subtropical and tropical regions. The extremelylow
content of the causative neurotoxins, designated as ciguatoxins,in
fish has hampered the isolation, detailed biological studies,and
preparation of anti-ciguatoxin antibodies for detecting thesetoxins.
The large (3 nanometers long) and complicated molecularstructure of
ciguatoxins has impeded chemists from completingtheir total synthesis.
Our highly convergent strategic approachfeaturing the chemoselective
ring-closing metathesis reactionas a key tactic has enabled the total
synthesis of ciguatoxinCTX3C, which will provide a practical supply
for further studies.
1 Department of Chemistry, Graduate School of
Science, Tohoku University, and CREST, Japan Science and Technology
Corporation (JST), Sendai 980-8578, Japan.
2 Department of Applied Bioorganic Chemistry,
Graduate School of Life Sciences, Tohoku University, Sendai 980-8555, Japan.
*
To whom correspondence should be addressed. E-mail:
hirama{at}ykbsc.chem.tohoku.ac.jp
Present address: Department of Chemistry, Graduate
School of Science, Osaka University, Osaka 560-0043, Japan.
Effect of Ciguatoxin 3C on Voltage-Gated Na+ and K+ Currents in Mouse Taste Cells.
V. Ghiaroni, H. Fuwa, M. Inoue, M. Sasaki, K. Miyazaki, M. Hirama, T. Yasumoto, G. P. Rossini, G. Scalera, and A. Bigiani (2006)
Chem Senses
31, 673-680
|Abstract »|Full Text »|PDF »
Natural Product Synthesis Special Feature: Prospects for total synthesis: A vision for a totally synthetic vaccine targeting epithelial tumors.
