Synthetic Studies on Bioactive Polycyclic Ethers

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Ciguatera poisoning is a toxicological syndrome resulting from the ingestion of seafood contaminated by certain toxic polycyclic ethers produced by the epiphytic dinoflagellate Gambierdiscus toxicus. The toxin suite comprises ciguatoxins, maitotoxin, and gambierol. Gambierol consists of a ladder-shaped trans-fused octacyclic ring system with 18 stereogenic centers. The total synthesis of gambierol has been achieved utilizing an oxiranyl anion strategy in an iterative manner. The synthetic route includes direct carbon. carbon formation on epoxides, sulfonyl. assisted 6.endo cyclization, and ring expansion reaction of tetrahydropyranyl rings to oxepanes to forge the polycyclic skeleton of the target molecule.