Total Synthesis of (±)-Poitediol and (±)-Dactylol

The unusual cyclooctanoid sesquiterpene, poitediol (7), was synthesized in racemic form in 20 steps from 2-methoxy-4-methyl-2-cyclohexen-l-one (14). The key step in the synthesis was the oxy-Cope rearrangement of 5-ethenyl-6-ethynyl-2-methylbicyclo[3.2.0]heptan-6-ol (22) to afford cis-1,2,3,3a,4,8-hexahydro-3-methyl-5H-cyclopentacycloocten-5-one (10). Racemic dactylol (8) was prepared in one step from poitediol by reduction with sodium in liquid ammonia.