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Total Syntheses of Diepoxy-Kaurane Diterpenoids Enabled by a Bridgehead-Enone-Initiated Intramolecular Cycloaddition.
J Am Chem Soc
December 2024
State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
Here, we report the enantioselective total syntheses of four diepoxy--kaurane diterpenoids including (-)-Macrocalin B, (-)-Acetyl-macrocalin B, and (-)-Isoadenolin A and the revised structure of (-)-Phyllostacin I, which hinges on the strategic design of a regioselective and stereospecific trapping of a highly reactive [3.2.1]-bridgehead enone intermediate via a tethered intramolecular Diels-Alder reaction.
View Article and Find Full Text PDFGoniodomic Acid, a Transient Oxirane Intermediate in the Conversion of the Macrolide Algal Toxin Goniodomin A to Seco Acids.
Chem Res Toxicol
December 2024
Department of Chemistry, Vanderbilt University, Nashville, Tennessee 37235, United States.
The algal macrolide goniodomin A (GDA) undergoes ring-cleavage under unusually mild, alkaline conditions to form mixtures of stereoisomers of seco acids GDA-sa and iso-GDA-sa. In the primary fragmentation pathway, opening of the macrolide ring occurs by displacement of the carboxyl group by a base-catalyzed attack of the C32 hemiketal hydroxy group on C31, yielding an oxirane-carboxylic acid, named goniodomic acid. The oxirane ring is unstable, undergoing solvolytic opening to form mainly GDA-sa.
View Article and Find Full Text PDFTriterpenoid phthalimides as selective anti-cancer agents targeting mitochondrial apoptosis.
Eur J Med Chem
February 2025
Laboratory of Medicinal and Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Medicine and Dentistry, Palacky University Olomouc, Hněvotínská 1333/5, 779 00, Olomouc, Czech Republic. Electronic address:
Starting from benzyl 30-oxobetulinate and 30-oxobetulin diacetate, substituted dienes were synthesized and subjected to Diels-Alder reaction, yielding a variety of triterpenoid phthalates, phthalimides, and related derivatives. A total of 55 new compounds were prepared and tested for in vitro cytotoxic activity against eight cancer cell lines and two non-cancerous cell lines. Four compounds with IC values of 5 μM or lower were selected for further investigation.
View Article and Find Full Text PDFComputational Insights into Tunable Reversible Network Materials: Accelerated ReaxFF Kinetics of Furan-Maleimide Diels-Alder Reactions for Self-Healing and Recyclability.
J Phys Chem A
December 2024
Department of Mechanical Engineering, Pennsylvania State University (PSU), University Park, Pennsylvania 16802, United States.
In this study, ReaxFF molecular dynamics simulations were benchmarked and used to study the relative kinetics of the retro Diels-Alder reaction between furan and -methylmaleimide. This reaction is very important for the creation of polymer networks with self-healing and recyclable properties, since they can be used as reversible linkers in the network. So far, the reversible Diels-Alder reaction has not yet been studied by using reactive molecular dynamics simulations.
View Article and Find Full Text PDFRevisiting the Enhanced Chemical Reactivity in Water Microdroplets: The Case of a Diels-Alder Reaction.
J Am Chem Soc
November 2024
Key Laboratory of Cluster Science of Ministry of Education, Beijing Key Laboratory of Photoelectronic/Electrophotonic Conversion Materials, School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081, China.
Often, chemical reactions are markedly accelerated in microdroplets compared with the corresponding bulk phase. While identifying the precise causative factors remains challenging, the interfacial electric field (IEF) and partial solvation are the two widely proposed factors, accounting for the acceleration or turning on of many reactions in microdroplets. In sharp contrast, this combined computational and experimental study demonstrates that these two critical factors have a negligible effect on promoting a model Diels-Alder (DA) reaction between cyclopentadiene and acrylonitrile in water microdroplets.
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