AI Article Synopsis
- Late-stage skeletal reorganization (LSSR) involving photochemical cascades is introduced for the first time in the synthesis of limonoid natural products, yielding nine unique compounds with five new structures.
- Quantum mechanical calculations reveal the mechanisms of these transformations, highlighting a novel ultraviolet light-driven approach for selective acyl migration.
- The findings suggest potential applications in the design of bioactive molecules and support the therapeutic use of xyloelf A in liver protection, paving the way for new drug discovery efforts.
Article Abstract
Late-stage skeletal reorganization (LSSR) is a type of fascinating organic transformation processes in natural product total synthesis. However, few facile and effective LSSR methodologies have hitherto been developed. Here, LSSR of limonoid natural products via photochemical cascades is first reported. Starting from xyloelves A and B, nine distinct limonoid products with five unprecedented scaffolds are generated. The photocascade pathways of these natural products and mechanistic rationale via intramolecular triplet energy transfer are revealed by quantum mechanical calculations. Most notably, ultraviolet light-driven transannular and stereoselective C → C 1,4-acyl migration is first found as a photochemical approach, particularly for LSSR of natural products. This approach holds promise for designing LSSR strategies to access bioactive cage-like molecules. Besides that, our findings provide a clear proof of concept for natural product photobiosynthesis. Xyloelf A, substantially ameliorating concanavalin A-induced liver injury in mice, could be used as a unique molecular template for hepatoprotective drug discovery.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC9882982 | PMC |
| http://dx.doi.org/10.1126/sciadv.ade2981 | DOI Listing |
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