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The efficient synthesis of pyranones is presented by a three-component cascade reaction from readily available acrylic acids, ethyl glyoxylate, and -toluenesulfonamide under ruthenium catalysis. For the first time, the nucleophilic addition of the vinylic C-H bond of acrylic acids across aldehyde is achieved, and the intramolecular cyclization as well as subsequent second insertion to aldehyde form the substituted butenolides. The elimination of sulfonamides occurs at higher temperature to give the pyranones.
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http://dx.doi.org/10.1021/acs.orglett.2c01614 | DOI Listing |
Org Lett
September 2025
Department of Chemistry and Chemical Biology, Northeastern University, Boston, Massachusetts 02115, United States.
An designed benzodioxin fused analogue of a des-(1-hydroxyethyl)-lincomycin analogue was synthesized in a asymmetric fashion from an achiral acylfuran, a 4-(-Pr)--methyl-proline, and catechol. The synthesis of the 6-amino-galactose portion of the lincomycin analogue necessitated the development of a novel stereospecific tandem Pd-glycosylation/1,4-addition reaction between catechol and an -Cbz-protected 6-amino-pyranone with a Pd-π-allyl leaving group at the -1 position. The desired -stereochemistry was installed by a subsequent stereoselective ketone reduction, alcohol elimination, and diastereoselective dihydroxylation of the -3/4 alkene.
View Article and Find Full Text PDFOrg Biomol Chem
August 2025
Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr Homi Bhabha Road, Pune-411008, India.
A simple and efficient synthesis of functionalized alkylidenephthalides, butenolides, pyranones, and isocoumarins was achieved using I-PPh-EtN reagent combination. The products obtained through this method act as versatile components in organic synthesis, enabling further modifications of functional groups. This method exhibits a wide substrate scope, employs straightforward and cost-effective reagents, eliminates the need for acidic, carbodiimide or other coupling agents, and operates at ambient temperature.
View Article and Find Full Text PDFChemistry
August 2025
Institute of Chemistry, University of Silesia in Katowice, Szkolna 9, Katowice, 40-006, Poland.
This study aimed to create new possibilities in the syntheses of aryl-arylethynyl-naphthalene and anthracene derivatives. Starting from simple structures, i.e.
View Article and Find Full Text PDFRSC Adv
May 2025
Chemistry Department, Faculty of Science, Mansoura University Mansoura 35516 Egypt +20-1093427024.
This review discusses the significant advances in the current status and latest synthesis techniques for -substituted 3-acetyl-4-hydroxyquinolinones. They are an important class of alkaloids possessing different electrophilic and nucleophilic centers. In this review, we comprehensively summarize the synthesis of 3-acetylquinolones various reactions, emphasizing recent developments and challenges.
View Article and Find Full Text PDFBioorg Chem
July 2025
Institute of Pharmacology, College of Medicine, National Yang Ming Chiao Tung University, Taipei 112304, Taiwan; Department of Pharmacy, School of Pharmaceutical Sciences, National Yang Ming Chiao Tung University, Taipei 112304, Taiwan; Department of Medical Research, China Medical University Hospit
Pogostemon cablin is a well-known Lamiaceae plant and widely utilized in Traditional Chinese Medicine (TCM) for its neuroprotective, anti-inflammatory, and anxiolytic properties. In this study, 16 known compounds (1-15 and 17) and one semi-synthesized new compound, 5-hydroxy-3-isoprenyloxy-7,3',4'-trimethoxyflavone (16), including flavonoids, pyranones, sesquiterpenes, and benzenoids, were obtained and characterized from aerial parts of P. cablin and investigated for their anti-inflammatory properties through the MAPK and NF-κB signaling pathways in LPS-induced RAW264.
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