Suzuki cross-coupling has been used to access a wide range of 3- and 5-substituted 2-pyrones, which show remarkable inhibitory activity against bacteria, yeasts and fungi. 3-Octenyl and 5-octenyl 2-pyrones inhibit human ovarium carcinoma (A2780) and human chronic myelogenous leukaemia (K562) cell lines at the micromolar level.
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Synthesis of acenaphthylene-fused heteroarenes and polyoxygenated benzo[]fluoranthenes via a Pd-catalyzed Suzuki-Miyaura/C-H arylation cascade.
Beilstein J Org Chem
December 2024
Department of Chemistry, Faculty of Science, Bilkent University, Ankara 06800, Türkiye.
Acenaphthylene-fused heteroarenes with a variety of five- and six-membered heterocycles such as thiophene, furan, benzofuran, pyrazole, pyridine and pyrimidine were synthesized via an efficient Pd-catalyzed reaction cascade in good to high yields (45-90%). This cascade involves an initial Suzuki-Miyaura cross-coupling reaction between 1,8-dihalonaphthalenes and heteroarylboronic acids or esters, followed by an intramolecular C-H arylation under the same conditions to yield the final heterocyclic fluoranthene analogues. The method was further employed to access polyoxygenated benzo[]fluoranthenes, which are all structurally relevant to benzo[]fluoranthene-based fungal natural products.
View Article and Find Full Text PDFTotal Syntheses of Indole Terpenoids (-)-Lyngbyatoxin, (-)-Teleocidin A2, and (-)-7-Geranylindolactam V.
J Org Chem
January 2025
Department of Chemistry and Biochemistry, Loyola University Chicago, Chicago, Illinois 60660, United States.
A regiodivergent palladium-catalyzed Suzuki-Miyaura reaction has been successfully implemented to synthesize (-)-lyngbyatoxin, (-)-teleocidin A2, and (-)-7-geranylindolactam V. This ligand-controlled cross-coupling strategy allowed for the direct preparation of these natural products from a single advanced synthetic intermediate, providing the shortest reported route to each compound. Subsequent studies in cancer cell lines were conducted to explore the chemotherapeutic applications of these natural products.
View Article and Find Full Text PDFA cross-shaped organic framework: a multi-functional template arranging chromophores.
Org Chem Front
December 2024
Department of Chemistry, University of Basel St Johanns-Ring 19 Basel 4056 Switzerland https://www.chemie1.unibas.ch/Bmayor/.
This work explores the use of a cross-shaped organic framework that is used as a template for the investigation of multi-functionalized chromophores. We report the design and synthesis of a universal cross-shaped building block bearing two bromines and two iodines on its peripheral positions. The template can be synthesized on a gram scale in a five-step reaction comprising an oxidative homo-coupling macro-cyclization.
View Article and Find Full Text PDFEnantioselective Synthesis of Isoindolinone by Sequential Palladium-Catalyzed Aza-Heck/Suzuki Coupling Reaction.
Org Lett
December 2024
School of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China.
We present a tandem aza-Heck/Suzuki cross-coupling reaction of -phenyl hydroxamic ethers with readily available arylboronic and alkenyl boronic acids. This protocol is enabled by a palladium catalyst paired with chiral phosphoramidite ligands, particularly under mild reaction conditions, yielding efficient and succinct synthetic routes to chiral isoindolinones with high enantioselectivity. Furthermore, this reaction exhibits excellent functional group compatibility and a rich diversity of subsequent transformations.
View Article and Find Full Text PDFOptically active cofacial ABCD-Pt(II)-porphyrin dimer exhibits bright circularly polarized phosphorescence.
Chem Commun (Camb)
December 2024
Department of Applied Chemistry for Environment, School of Biological and Environmental Sciences, Kwansei Gakuin University 1 Gakuen Uegahara, Sanda, Hyogo 669-1330, Japan.
Article Synopsis
- The synthesis of a chiral cofacial ABCD-Pt(II)-porphyrin dimer was successfully completed using a Pt-templated method followed by a Suzuki-Miyaura cross-coupling process.
- The resulting enantiomers showcased bright red circularly polarized phosphorescence.
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