ja208018s_si_002.cif (20.57 kB)
Enantioselective Total Synthesis of Aplyviolene
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posted on 2011-10-19, 00:00 authored by Martin J. Schnermann, Larry E. OvermanThe enantioselective total synthesis of the rearranged spongian diterpene aplyviolene has been completed in 14 steps from the known hydroazulenone 8. 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.
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Enantioselectivestereoselectivityhydroazulenone 8.hydrocarbonMichael additionspongian diterpene aplyvioleneoxygenated fragmentsSynthesienantioenriched hydroazulenone enolatejunctionbromocyclopentenone14 stepsC 8 quaternary carbon stereocenterenantiopureAplyvioleneThe enantioselectivebicyclic lactone functionalitysynthesis
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