ArticleJournal of the American Chemical Society2011
Enantioselective total synthesis of aplyviolene.
Article in Journal of the American Chemical Society, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
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Who cites it
9 citing papers in PubMed.
- Acridine Photocatalysis: Insights into the Mechanism and Development of a Dual-Catalytic Direct Decarboxylative Conjugate Addition.ACS catalysis · 2020Article
- Illuminating Photoredox Catalysis.Trends in chemistry · 2019Article
- Navigating the Chiral Pool in the Total Synthesis of Complex Terpene Natural Products.Chemical reviews · 2017Review
- Radicals: Reactive Intermediates with Translational Potential.Journal of the American Chemical Society · 2016Review
- Photoredox Catalysis in Organic Chemistry.The Journal of organic chemistry · 2016Article
- Total Synthesis of (-)-Chromodorolide B.Journal of the American Chemical Society · 2016Article
- Forming tertiary organolithiums and organocuprates from nitrile precursors and their bimolecular reactions with carbon electrophiles to form quaternary carbon stereocenters.Angewandte Chemie (International ed. in English) · 2012Article
- A concise synthesis of (-)-aplyviolene facilitated by a strategic tertiary radical conjugate addition.Angewandte Chemie (International ed. in English) · 2012Article
- Constructing molecular complexity and diversity: total synthesis of natural products of biological and medicinal importance.Chemical Society reviews · 2012Review
Corrections and comments
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Authors and funding
2 authors.
Funding
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 α-bromocyclopentenone.
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Registered trials
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