ArticleAngewandte Chemie (International ed. in English)2021
Synthesis of (±)-Setigerumine I: Biosynthetic Origins of the Elusive Racemic Papaveraceae Isoxazolidine Alkaloids*.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed.
- Study of Cytotoxicity of Pyrrolo[3,4-International journal of molecular sciences · 2026Article
- Harnessing Photochemistry in Natural Product Synthesis: From Strategy to Applications.Journal of natural products · 2025Review
- Intramolecular N-O Bond Formation for the Synthesis ofJournal of the American Chemical Society · 2025Article
- Studies of the Synthesis of Fused Isoxazoline/Isoquinolinones and Evaluation of the Antifungal Activity of Isoxazole-like Benzamide and Isoquinolinone Hybrids.Molecules (Basel, Switzerland) · 2025Article
- New 3-(Dibenzyloxyphosphoryl)isoxazolidine Conjugates of N1-Benzylated Quinazoline-2,4-diones as Potential Cytotoxic Agents against Cancer Cell Lines.Molecules (Basel, Switzerland) · 2024Article
- In Silico Design, Synthesis, and Evaluation of Novel Enantiopure Isoxazolidines as Promising Dual Inhibitors of α-Amylase and α-Glucosidase.Molecules (Basel, Switzerland) · 2024Article
- Demystifying racemic natural products in the homochiral world.Nature reviews. Chemistry · 2022Review
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3 authors.
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Abstract
The biosynthetic origins of the structurally related racemic isoxazolidine Papaveraceae alkaloids Setigerumine I, Dactylicapnosinine and Dactylicapnosine have remained elusive since their original isolation over two decades ago. Herein we report the first biosynthetic hypothesis for their formation and, inspired by it, the first synthesis of (±)-Setigerumine I with accompanying computational rationale. Based on the results, these isoxazolidine alkaloids arise from racemizing oxidative rearrangements of prominent isoquinoline alkaloids Noscapine and Hydrastine. The key steps featured in this synthesis are a room temperature Cope elimination and a domino oxidation/inverse-electron demand 1,3-dipolar cycloaddition of an axially chiral, yet configurationally unstable, intermediate. The work opens this previously inaccessible family of natural products for biological studies.
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