ArticleAngewandte Chemie (International ed. in English)2020
Total Synthesis of (±)-Phyllantidine: Development and Mechanistic Evaluation of a Ring Expansion for Installation of Embedded Nitrogen-Oxygen Bonds.
Article in Angewandte Chemie (International ed. in English), 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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12 citing papers in PubMed.
- Strategic Applications of Single-Atom Skeletal Editing in Natural Product Synthesis.Journal of the American Chemical Society · 2026Review
- Enantioselective NHC-Catalyzed Annulation via Umpolung for the Construction of Hydroxylamine Architectures with Variable Ring Sizes.Organic letters · 2025Article
- The Enantioselective Total Synthesis of (+)-3-Ketobrassicicene W and (-)-Alterbrassicicene B.Organic letters · 2025Article
- Intramolecular N-O Bond Formation for the Synthesis ofJournal of the American Chemical Society · 2025Article
- Total Synthesis of (-)-Flueggeacosine C.Organic letters · 2024Article
- Catalytic Asymmetric Access to Structurally DiverseJACS Au · 2024Article
- Conglomerate Crystallization in the Cambridge Structural Database (2020-2021).Crystal growth & design · 2023Article
- [3+3]-Annulation of Cyclic Nitronates with Vinyl Diazoacetates: Diastereoselective Synthesis of Partially Saturated [1,2]Oxazino[2,3-Molecules (Basel, Switzerland) · 2023Article
- Collective total synthesis of C4-oxygenated securinine-type alkaloids via stereocontrolled diversifications on the piperidine core.Nature communications · 2022Article
- A Ring Expansion Approach ToTetrahedron letters · 2022Article
- Catalytic Reduction of Oximes to Hydroxylamines: Current Methods, Challenges and Opportunities.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Review
- Phosphite mediated asymmetric N to C migration for the synthesis of chiral heterocycles from primary amines.Chemical science · 2021Article
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7 authors.
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Abstract
The development of a concise total synthesis of (±)-phyllantidine (1), a member of the securinega family of alkaloids containing an unusual oxazabicyclo[3.3.1]nonane core, is described. The synthesis employs a unique synthetic strategy featuring the ring expansion of a substituted cyclopentanone to a cyclic hydroxamic acid as a key step that allows facile installation of the embedded nitrogen-oxygen (N-O) bond. The optimization of this sequence to effect the desired regiochemical outcome and its mechanistic underpinnings were assessed both computationally and experimentally. This synthetic approach also features an early-stage diastereoselective aldol reaction to assemble the substituted cyclopentanone, a mild reduction of an amide intermediate without N-O bond cleavage, and the rapid assembly of the butenolide found in (1) via use of the Bestmann ylide.
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