Total synthesis of ciguatoxin CTX3C.
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.
Hirama
M
M
Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan. hirama@ykbsc.chem.tohoku.ac.jp
Oishi
T
T
Uehara
H
H
Inoue
M
M
Maruyama
M
M
Oguri
H
H
Satake
M
M
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D002922:Ciguatoxins / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology / Q000633:toxicity; D002942:Circular Dichroism; D004141:Dinoflagellida / Q000737:chemistry*; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D017747:Seafood / Q000469:parasitology / Q000506:poisoning
D002922:Ciguatoxins