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.