The Journal of Organic Chemistry· 2026Q2
Total Syntheses and Biological Evaluation of Lamellolactones A and B via Direct Butenolide Functionalization
- 1citations
- Q2SCImago
- 2026year
Short summary
Researchers report the first total syntheses of lamellolactones A and B, natural products linked to fibrodysplasia ossificans progressiva (FOP), using a novel Ni-catalyzed reductive coupling of alkyl iodides with bromobutenolides.
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Key points
- First total syntheses of lamellolactones A and B achieved.
- A novel Ni-catalyzed reductive coupling of alkyl iodides with α- and β-bromobutenolides was employed.
- The synthetic route is applicable to primary and secondary alkyl iodides.
- Analogues were synthesized to investigate the impact of γ-substitution on biological activity.
AI-generated from the title and abstract; the full text is not read.
Abstract
Abstract Lamellolactones A and B are pseudoregioisomeric natural products bearing oxidized butenolide frameworks and have attracted interest in the context of fibrodysplasia ossificans progressiva (FOP). We achieved their first total syntheses via Ni-catalyzed reductive coupling of a common alkyl iodide with α- and β-bromobutenolides. A preliminary examination of alkyl electrophiles indicated that the coupling could be applied to simple primary and secondary alkyl iodides. The route also furnished analogues for comparison of γ-substitution effects on bone morphogenetic protein (BMP)-induced alkaline phosphatase inhibition and cytotoxicity.
The authors' abstract, as published at the source. The Journal of Organic Chemistry, 2026 · DOI ↗
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Field: Organic Chemistry
Organic ChemistryChemistry