PubMed · 3687667
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M A Hull. 1987. Ciguatera toxicity.. https://pubmed.ncbi.nlm.nih.gov/3687667/
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[reaction: see text] A convergent synthesis of the right-hand half of ciguatoxin (the HIJKLM ring system) has been achieved with complete stereocontrol in the introduction of the stereocenters on the eight-membered I ring. Key steps are Sonogashira coupling, dicobalt complexation, intramolecular conjugate addition, and hydrogenation of an endo-olefin to provide the 39-alpha-methyl group.
Gambierol, a representative of the marine ladder toxin family, consists of eight ether rings, 18 stereocenters, and two challenging pyranyl rings having methyl groups that are in a 1,3-diaxial orientation to one another. Herein we describe the generation of gambierol's A-C and F-H ring systems and demonstrate the versatility of the glycosyl anhydride, enol ether-olefin RCM strategy to fused polycyclic ethers. This work has both enabled us to generate sufficient quantities of the gambierol precursors and has enabled us to better understand the chemical transformations that were key to these efforts. Fundamental work included efforts to C-glycosides and C-ketosides, Claisen rearrangements, and enol ether-olefin RCM reactions.
[structure: see text] Ciguatoxin CTX3C is a representative congener of ciguatoxins, which are known to be the principal causative agents of ciguatera seafood poisoning. The structure of CTX3C spans more than 3 nm and is characterized by 13 ether rings. In this paper, an improved total synthesis of CTX3C is reported. Alteration of the protective group from benzyl ether to 2-naphthylmethyl (NAP) ether drastically increases the yield for final global deprotection and has provided a sufficient amount of sample for further biological studies.