Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 41, Pages 16425-16427Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja208018s
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Funding
- NIH Neurological Disorders & Stroke Institute [NS-12389]
- NIH National Institutes of General Medical Sciences [GM-098601]
- NIH [CA-138084]
- NSF
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The 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 alpha-bromocyclopentenone.
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