An asymmetric [4 + 2] cycloaddition of β,γ-unsaturated α-keto esters with 2-vinylpyrroles in water was developed under the catalysis of a kind of copper complex with a low loading. A series of optically pure 3,4-dihydro-2-pyran derivatives could be obtained in excellent yields, with high diastereoselectivities and enantioselectivities. The corresponding mechanism was proposed, which was supported by DFT calculations.
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http://dx.doi.org/10.1021/acs.orglett.2c01544 | DOI Listing |
Mar Drugs
December 2024
Shandong Laboratory of Yantai Drug Discovery, Bohai Rim Advanced Research Institute for Drug Discovery, Yantai 264117, China.
Two new cembrane-derived tricyclic diterpenes belonging to the sarcophytin family, namely 4-hydroxy-chatancin () and sarcotoroid (), together with two known related ones ( and ), were isolated from the soft coral collected off Ximao Island in the South China Sea. The structures of the new compounds were elucidated by extensive spectroscopic analysis, a quantum mechanical nuclear magnetic resonance (QM-NMR) method, a time-dependent density functional theory electronic circular dichroism (TDDFT-ECD) calculation, X-ray diffraction analysis, and comparison with the reported data in the literature. A plausible biosynthetic pathway of compounds - was proposed, involving undergoing a transannular Diels-Alder cycloaddition.
View Article and Find Full Text PDFMacromol Rapid Commun
December 2024
Hunan Key Laboratory of Micro & Nano Materials Interface Science, College of Chemistry and Chemical Engineering, Central South University, Changsha, 410083, China.
The CO-epoxide addition to cyclic carbonate is of great significance but usually requires high temperatures and CO pressures. Herein, a spirobifluorene-based porous organic polymer catalyst is designed with a Co-salen complex immobilized on the backbone (ST-CoSalen-POP) to enable CO fixation under mild conditions. ST-CoSalen-POP possesses a high Co-loading content (9.
View Article and Find Full Text PDFJ 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 PDFOrg Lett
December 2024
Guangxi Key Laboratory of Natural Polymer Chemistry and Physics, Nanning Normal University, Nanning 530001, P. R. China.
A palladium-catalyzed [2π + 2σ] cycloaddition of vinyl bicyclo[1.1.0]butanes with methyleneindolinones has been developed.
View Article and Find Full Text PDFAnal Chem
December 2024
NMPA Key Laboratory for Research and Evaluation of Drug Metabolism & Guangdong Provincial Key Laboratory of New Drug Screening & Guangdong-Hongkong-Macao Joint Laboratory for New Drug Screening, School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China.
A simple, rapid, and visual approach is developed to perform diagnosis of urinary tract infection (UTI) and antimicrobial susceptibility testing (AST) by employing smart bifunctional DNA (bfDNA) sensors, exonuclease III, concatermers of CuO nanoparticles (CuONPs), and gold NPs (AuNPs) aggregation [AuNPs agglutination (AA)], namely, the bfDEC-AA method. The bfDNA sensors serve as probes for identifying 16S rRNA genes of bacterium or 18S rRNA of fungus and as mediators connecting the concatermers of CuONPs. The AA as a signal source is triggered by Cu(I)-catalyzed azide-alkyne cycloaddition click chemistry.
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