syn-trans Fused Bicyclic Ether Formation via Acetylene-biscobalthexacarbonyl Complex

Abstract
Medium size bicyclic ethers of 7-, 8-, and 9-membered rings were synthesized by connection between a hydroxy group on dihydropyranyl ring and a propargylic cation that was stabilized as an acetylene biscobalthexacarbonyl complex under acidic conditions. This cyclization selectively afforded the syn-trans bicyclic ring system often seen in marine toxins such as ciguatoxin.