ArticleAngewandte Chemie (International ed. in English)2022
Bioinspired Asymmetric Total Synthesis of Emeriones A-C.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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4 citing papers in PubMed.
- Oxygen-Oxygen Bond-Forming Reactions for the Synthesis of Cyclic Peroxides.Journal of the American Chemical Society · 2026Article
- Article
- Catalytic Enantioselective Hydrogen Atom Abstraction Enables the Asymmetric Oxidation ofJournal of the American Chemical Society · 2024Article
- Bioinspired Asymmetric Total Synthesis of Emeriones A-C.Angewandte Chemie (International ed. in English) · 2022Article
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5 authors.
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Abstract
We report asymmetric bioinspired total syntheses of the fungal metabolites emeriones A-C via stereoselective oxidations of two bicyclo[4.2.0]octadiene diastereomers. The central bicyclic scaffolds are prepared in an 8π/6π electrocyclization cascade of a stereodefined pentaene, which contains the fully assembled side chains of the emeriones. The anti-aldol side chain is made using a Paterson-aldol addition, and the epoxide of the dioxabicyclo[3.1.0]hexane side chain via ring-closure onto an oxidized acetal. Our work has enabled the structural revision of emerione C, and resulted in the synthesis of a "missing" family member, which we call emerione D. DFT calculations identified two methyl groups that govern torquoselectivity in the 8π/6π cascade.
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