Enantioselective Total Synthesis of Aplyviolene Martin J. Schnermann Larry E. Overman 10.1021/ja208018s.s001 https://acs.figshare.com/articles/journal_contribution/Enantioselective_Total_Synthesis_of_Aplyviolene/2599861 The enantioselective total synthesis of the rearranged spongian diterpene aplyviolene has been completed in 14 steps from the known hydroazulenone <b>8</b>. The key junction of the hydrocarbon and oxygenated fragments to form the critical C8 quaternary carbon stereocenter and set the stage for elaborating the delicate bicyclic lactone functionality was accomplished in high yield and exquisite stereoselectivity by Michael addition of an enantioenriched hydroazulenone enolate to an enantiopure α-bromocyclopentenone. 2011-10-19 00:00:00 Enantioselective stereoselectivity hydroazulenone 8. hydrocarbon Michael addition spongian diterpene aplyviolene oxygenated fragments Synthesi enantioenriched hydroazulenone enolate junction bromocyclopentenone 14 steps C 8 quaternary carbon stereocenter enantiopure AplyvioleneThe enantioselective bicyclic lactone functionality synthesis