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Enantioselective total synthesis of aplyviolene.

ABSTRACT: 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 ?-bromocyclopentenone.

SUBMITTER: Schnermann MJ

PROVIDER: S-EPMC3205941 | biostudies-other | 2011 Oct

REPOSITORIES: biostudies-other

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Enantioselective total synthesis of aplyviolene.

Schnermann Martin J MJ Overman Larry E LE

Journal of the American Chemical Society 20110923 41

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 α-bromocyc ...[more]

PMID: 21936525

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