In this communication, we report a copper catalyzed sequential arylation-oxidative dimerization reaction as the key step for the synthesis of hexahydropyrroloindole alkaloids (+)-chimonanthine, (+)-folicanthine and (-)-calycanthine.
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http://dx.doi.org/10.1039/c5cc05378a | DOI Listing |
J Org Chem
December 2024
Institute of BioPharmaceutical Sciences, National Sun Yat-sen University, No. 70, Lien-hai Road, Kaohsiung 804201, Taiwan.
This paper presents a copper(I)-catalyzed intramolecular tandem acylation/-arylation of methyl 2-[2-(2-bromophenyl)acetamido]benzoates for the synthesis of benzofuro[3,2-]quinolin-6(5)-ones under mild conditions. The combination of CuI, 1,10-phenanthroline, and KCO in DMSO was found to be the optimal reaction condition, producing the target products in high yields (84-99%) at 70 °C for 16 h. The tandem reaction was applicable to substrates bearing halo, electron-withdrawing, and electron-donating groups at their phenyl moieties with a broad substrate scope.
View Article and Find Full Text PDFJ Am Chem Soc
December 2024
State Key Laboratory of Structural Chemistry, Center for Excellence in Molecular Synthesis, Fujian Institute of Research on the Structure of Matter, University of Chinese Academy of Sciences, Fuzhou 350100, China.
Catalytic asymmetric transformation of donor-acceptor cyclopropanes (DACs) has been proven to be a highly valuable and robust strategy to construct diverse types of enantioenriched molecules. However, the use of 1,1,2,2-tetrasubstituted DACs to form products bearing quaternary stereocenters remains a long-term unsolved challenge. Here, we report the copper-catalyzed asymmetric aminative ring opening of tetrasubstituted alkynyl DACs that delivers a myriad of α-tertiary amines with high levels of enantioselectivities.
View Article and Find Full Text PDFAnal Chem
December 2024
Key Laboratory of Dairy Science, Ministry of Education, College of Food Science, Northeast Agricultural University, Harbin 150030, China.
is one of the most dangerous and contagious foodborne pathogens, posing a significant threat to public health and food safety. In this study, we developed a click chemistry-based fluorescence biosensing platform for highly sensitive detection of () by integrating the -cleavage activity of CRISPR/Cas12a with the CLICK17-mediated copper(II)-dependent azide-alkyne cycloaddition (Cu(II)AAC) click reaction. Herein, CLICK-17 can provide binding sites for Cu ions and high redox stability for one or much catalytically vital Cu within its active sites, which facilitate the click reaction.
View Article and Find Full Text PDFChemistry
December 2024
Guangdong Pharmaceutical University, Guangzhou Higher Education Mega Center, 510006, Guangzhou, CHINA.
Among the various studies on CO2 utilization, the sustainable and cost-effective fixation of CO2 into cyclic carbonates remains one of the most intriguing subjects. To this end, a novel type of composite dicationic ionic liquid material, DIL@PDIL, was developed. This composite consists of a dicationic ionic liquid (DIL), DMAP[TMGH]Br, supported on a polymeric dicationic ionic liquid (PDIL), P-DVB/Im[TMGH]Br.
View Article and Find Full Text PDFClin Exp Metastasis
December 2024
Christopher S. Bond Life Sciences Center 540F, University of Missouri, 1201 E Rollins, Columbia, MO, 65211, USA.
Copper promotes tumor growth and metastasis through a variety of mechanisms, most notably as a cofactor within the lysyl oxidase (LOX) family of secreted cuproenzymes. Members of this family, which include LOX and LOX-like enzymes LOXL1-4, catalyze the copper-dependent crosslinking of collagens and elastin within the extracellular matrix (ECM). Elevated LOX expression is associated with higher incidence and worse prognosis in multiple cancers, including colorectal, breast, pancreatic, and head and neck.
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