Synthetic Studies on Ciguatoxin: A Convergent Strategy for Construction of the F-M Ring Framework

Exceptional neurotoxicity is associated with ciguatoxin. The ciguatoxin mimic 1, which contains the F–M framework of the natural product, has been prepared through a convergent synthesis. The two key steps were a Lewis acid mediated intramolecular reaction of a γ-alkoxyallylsilane with an acetal group and an SmI2-mediated intramolecular Reformatsky reaction that permitted construction of the annelated hexahydrooxonin ring system.