Total synthesis of ciguatoxin CTX3C: a venture into the problems of ciguatera seafood poisoning

Abstract

AbstractAfter a twelve‐year struggle, the total synthesis of ciguatoxin CTX3C has been achieved. Annually, more than 20,000 people worldwide suffer from ciguatera seafood poisoning. The extremely small amounts of the causative neurotoxin, ciguatoxin, in fish hampered the isolation, structural elucidation, detailed biological study, and preparation of anti‐ciguatoxin antibodies for detecting these toxins. The large (3 nanometers long) and complicated molecular structure of ciguatoxins hindered chemists from completing a total synthesis. The chemical synthesis of CTX3C, determination of the absolute configuration, and synthesis‐based preparation of the monoclonal antibodies as well as the effect of synthetic CTX3C on voltage‐sensitive sodium channels are outlined. © 2005 The Japan Chemical Journal Forum and Wiley Periodicals, Inc. Chem Rec 5: 240–250; 2005: Published online in Wiley InterScience (www.interscience.wiley.com) DOI 10.1002/tcr.20049