Synthetic Studies on Bioactive Polycyclic Ethers

雪卡毒中毒是一种中毒综合症，是由于进食受附生甲藻Gambierdiscus toxicus所产生的有毒多环醚污染的海产而引致。毒素组包括雪卡毒素、舞毒蛾毒素和甘比洛尔。甘比尔醇是由一个梯形的八环反式稠合环系统组成，具有18个立体异构中心。采用环氧乙烷基阴离子策略，以迭代方式实现了甘比尔醇的全合成。合成路线包括直接碳。环氧化物上的碳形成，磺酰基。辅助的6.内环化和四氢吡喃环的扩环反应，以形成目标分子的多环骨架。

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.