The use of Cinchona alkaloid-based chiral ammonium ylides allows for the first highly enantioselective and broadly applicable spirocyclopropanation reactions of para-quinone methides. This strategy provides a straightforward protocol toward the chiral spiro[2.5]octa-4,7-dien-6-one skeleton, which is a frequently found structural motif in important biologically active molecules.
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http://dx.doi.org/10.1021/acs.orglett.7b00869 | DOI Listing |
J Am Chem Soc
January 2025
Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China.
Axially chiral -VQMs have been extensively investigated as key intermediates to approach miscellaneous chiral structures. By sharp contrast, their structural isomers -VQMs have not been previously documented. The major reason, which results in the significant delay, may ascribe to the inherent challenges in the enantioselective activation of alkynes in a remote manner.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
Frontier Institute of Science and Technology, Xi'an Jiaotong University, Xi'an, Shaanxi, 710054, China.
Although great advancement has been made in synthesis of 3D bridged bicyclic[n.1.1]-bioisosteres, facile construction of 2D/3D merged molecules incorporating bridged rings, as novel chemical space in drug discovery, remains a significant challenge.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Department of chemistry, Pondicherry University, Puducherry-605014, India.
We present a method for synthesizing -benzyl pyridones from -quinone methides (-QMs) and 2- or 4-hydroxy pyridines in the presence of a base at room temperature. The reaction proceeds through 1,6-Michael addition reaction. Simple operation, good to excellent yields, broad substrate scope, and good functional group tolerance are the salient features of the developed methodology.
View Article and Find Full Text PDFFront Pharmacol
October 2024
State Key Laboratory for Macromolecule Drugs and Large-Scale Manufacturing, School of Pharmaceutical Sciences, Liaocheng University, Liaocheng, China.
A series of -quinone methide derivatives were evaluated their anti-inflammatory activity. Through the screening of the lipopolysaccharide (LPS)-induced inflammatory cell model in Raw264.7 cells, it was found that the inhibitory activity of -substituted derivatives on NO production was superior to that of - and -substituted derivatives.
View Article and Find Full Text PDFJ Org Chem
November 2024
College of Pharmacy, National & Local Joint Engineering Research Center of Targeted and Innovative Therapeutics, IATTI, Chongqing University of Arts and Sciences, Chongqing 402160, China.
Sulfonylhydrazones have been proven to be versatile synthetic intermediates in a panel of transformations. However, radical sulfonylation with sulfonylhydrazone as sulfonyl radical source is relatively rare. Here, we found that sulfonylhydrazone can serve as a new sulfonyl radical precursor to couple various partners such as arylacetic acids, ene-yne-ketones, and -quinone methides under copper catalysis and microwave irradiation.
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