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DNA-compatible one-pot synthesis of multi-substituted dihydrofuran pyridinium ylide-mediated cyclization.
Org Biomol Chem
January 2025
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, China.
Synthesis of chemically diverse heterocyclic scaffolds in DNA-encoded libraries is highly demanded. We herein reported a convenient one-pot multi-component on-DNA synthetic strategy to afford multi-substituted 2,3-dihydrofuran scaffolds pyridinium ylide-mediated cyclization. This reaction exhibited modest to excellent conversions for a broad range of DNA-conjugated aldehydes, β-ketonitriles and pyridinium salts under mild reaction conditions.
View Article and Find Full Text PDFUses of Cyclohexan-1,3-diones to Synthesis Xanthenes Derivatives with Anti-proliferative Activity Against Cancer Cell Lines and their Inhibitions Toward Tyrosine Kinases.
Anticancer Agents Med Chem
January 2025
Department of Chemistry, Faculty of Science, Cairo University, A. R, Egypt.
Background: Xanthene derivatives are a notable class of heterocyclic compounds widely studied for their significant biological impact. These molecules, found in both natural and synthetic forms, have attracted substantial scientific interest due to their broad spectrum of biological activities. The xanthene nucleus, in particular, is associated with a range of potential pharmaceutical properties, including antibacterial, antiviral, antiinflammatory, anticancer, and antioxidant effects.
View Article and Find Full Text PDFCascade Aza-Prins/Friedel-Crafts Reaction of Homocinnamyloxycarbamate and Aromatic Aldehydes Yielding Aromatic Ring-Annulated Hydrocyclopenta-1,2-oxazinane.
J Org Chem
January 2025
Applied Chemistry and Chemical Engineering, Graduate School of Engineering, Kogakuin University, Nakano 2665-1, Hachioji, Tokyo 192-0015, Japan.
The cascade aza-Prins/Friedel-Crafts reaction of homocinnamyloxycarbamate with electron-rich aromatic aldehydes has been successfully established. Most of the aromatic aldehydes react with the carbamate stereoselectively to generate -hydroindeno-1,2-oxazinanes. However, the cascade reactions of benzaldehydes bearing two methoxy groups at the -positions exhibit a unique stereochemical profile.
View Article and Find Full Text PDFAnnulative Coupling of Sulfoxonium Ylides with Aldehydes and Naphthols or Coumarins: Easy Access to Fused Dihydrofurans.
J Org Chem
January 2025
Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221005, India.
We present a novel, metal- and additive-free method for the robust synthesis of dihydrofuran-fused naphthalenes and coumarins. This approach utilizes the annulative coupling of sulfoxonium ylides with aldehydes, naphthols, or coumarins at ambient temperature. The method exhibits broad substrate compatibility, accommodating various functional groups on sulfoxonium ylides and naphthol or coumarin derivatives and resulting in good to high yields of the desired products.
View Article and Find Full Text PDFTaming Highly Enolizable Aldehydes via Enzyme Catalysis for Enantiocomplementary Construction of β-Hydroxyphosphonates.
J Am Chem Soc
January 2025
State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China.
Taming highly enolizable aldehydes for catalytic asymmetric C-C coupling with nucleophiles remains an elusive challenge compared to widely explored simple alkyl or aryl aldehydes. Herein, we use ThDP-dependent enzymes to realize the direct C-C coupling of highly enolizable 2-phosphonate aldehydes with in situ-generated dynamically reversible nucleophiles (acyl anions). Unlike NHC-mediated reactions that yield complex mixtures of multiple adducts, our enzymatic process selectively produces biologically active β-hydroxy phosphonates with high yields (up to 95%) and excellent enantioselectivities (up to 99% ee).
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