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