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Experimental and DFT Studies of Intermolecular Interaction-Assisted Oxindole Cyclization Reaction of Di-t-butyl 2-Aminophenyl-2-methyl Malonate.
Chem Pharm Bull (Tokyo)
January 2025
Department of Life Science and Biotechnology, Faculty of Chemistry, Materials and Bioengineering, Kansai University, 3-3-35 Yamate-cho, Suita, Osaka 564-8680, Japan.
Density functional theory calculations on the cyclization of di-t-butyl 2-(2-aminophenyl)-2-methyl malonate (1) to t-butyl 3-methyloxindole-3-carboxylate (2) reveal that acetic acid-assisted protonation of the carbonyl oxygen atom reduces the activation Gibbs free energy significantly lower than methanol-assisted pathways. Experimental data confirm that reaction concentration plays a pivotal role in oxindole formation. Experimental results also indicate distinct reaction mechanisms at low and high concentrations.
View Article and Find Full Text PDFRuthenium-Catalyzed Intramolecular Allene-alkyne Cascade Cyclization: Access to the Sulfone-cyclopenta[]naphthalene Core.
Org Lett
January 2025
Department of Chemistry, Indian Institute of Technology Ropar, Rupnagar, Punjab 140001, India.
A ruthenium-catalyzed intramolecular cascade cyclization of allene-alkyne has been achieved. This method offers a streamlined and atom-economical approach for the construction of sulfone bearing 1-cyclopenta[]naphthalenes, an important structural scaffold that exists in biologically active compounds. Our approach, backed by mechanistic insights from deuterium labeling, DFT calculations, and potential for reaction scale-up, presents synthetic chemists with an invaluable tool for efficiently producing a distinct carbon framework in a one-pot manner.
View Article and Find Full Text PDFA new diterpenoid, carneadiol, isolated from Nocardia carnea IFM 12324.
J Nat Med
January 2025
Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba, 260-8675, Japan.
A new diterpenoid, carneadiol (1), with an unprecedented tricyclic carbon skeleton, was isolated from the culture extracts of Nocardia carnea IFM 12324. The structure of compound 1 was elucidated using spectral studies, including various NMR data. The absolute configuration of 1 was determined using X-ray crystallographic analysis with the crystalline sponge method.
View Article and Find Full Text PDFCobalt-Cluster-Based Metal-Organic-Framework-Catalyzed Carboxylative Cyclization of Propargylic Amines with CO from Flue Gas.
Inorg Chem
January 2025
Frontiers Science Center for New Organic Matter, Key Laboratory of Advanced Energy Materials Chemistry (MOE), College of Chemistry, Nankai University, Tianjin 300071, China.
The fixation of carbon dioxide (CO) directly from flue gas into valuable chemicals like 2-oxazolidinones is of great significance for economic and environmental benefits, which is typically catalyzed by noble-metal catalysts and under harsh conditions. Herein, a novel 2-fold interpenetrated framework {[Co(μ-O)(TCA)(HDPTA)]·2HO·2DMF} [Co(II)-based metal-organic framework ()] containing [Co] clusters and highly dense amino groups (-NH) dispersed in the channel was prepared, exhibiting high solvent/pH stability and CO adsorption capacity (24.9 cm·g).
View Article and Find Full Text PDFSystematic molecular dissection of key intermediates in xanthones biosynthesis in Cudrania tricuspidata and establishment of a viable heterologous expression system.
Plant Physiol Biochem
January 2025
Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, Jinan, Shandong, 250012, China. Electronic address:
The major phytochemicals in the roots of Cudrania tricuspidata are prenylated xanthones, exhibiting significant structural diversity and bioactive properties, such as anti-inflammatory, antioxidative, and antitumor effects. The biosynthetic pathways of these compounds have not yet been resolved, limiting their production through synthetic biology. In this study, benzoyl-coenzyme A (CoA) ligase (BZL), benzophenone synthase (BPS), and benzophenone 3'-hydroxylase (B3'H) transcripts involved in the biosynthesis of xanthone were cloned and characterized from C.
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