Report

Total Synthesis of Ciguatoxin CTX3C

Science  30 Nov 2001:
Vol. 294, Issue 5548, pp. 1904-1907
DOI: 10.1126/science.1065757

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Abstract

More than 20,000 people suffer annually from ciguatera seafood poisoning in subtropical and tropical regions. The extremely low 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 these toxins. The large (3 nanometers long) and complicated molecular structure of ciguatoxins has impeded chemists from completing their total synthesis. Our highly convergent strategic approach featuring the chemoselective ring-closing metathesis reaction as a key tactic has enabled the total synthesis of ciguatoxin CTX3C, which will provide a practical supply for further studies.

  • * 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.

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