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Mechanistic Study of B(CF)-Catalyzed Transfer Hydrogenation of Aldehydes/Ketones with PhSiH and Stoichiometric Water.
ACS Omega
January 2024
Faculty of Materials and Chemical Engineering, Yibin University, Yibin 644000, Sichuan, People's Republic of China.
A DFT study was performed on the mechanisms of B(CF)-catalyzed transfer hydrogenation of aldehydes/ketones, using PhSiH and stoichiometric water. Path B2 includes a stepwise Piers S2-Si process, H transfer, and hydrolysis desilylation of siloxane, in which the hydrolysis desilylation step is rate-determining. Path C1 is first determined, involving a B(CF)-catalyzed concerted addition step of 2HO to carbonyl generating RRC(OH), a subsequent S2-Si dehydroxylation step of RRC(OH) giving RRC=OH and (CF)B-H, and final H transfer producing the respective alcohol RRCHOH.
View Article and Find Full Text PDFFacile Access to Structurally Diverse Antimalarial Indoles Using a One-Pot A Coupling and Domino Cyclization Approach.
ChemMedChem
September 2023
Research Institute for Medicines (iMed.ULisboa), Faculdade de Farmácia da Universidade de Lisboa, Av. Prof. Gama Pinto, 1649-003, Lisboa, Portugal.
A multistep and diversity-oriented synthetic route aiming at the A coupling/domino cyclization of o-ethynyl anilines, aldehydes and s-amines is described. The preparation of the corresponding precursors included a series of transformations, such as haloperoxidation and Sonogashira cross-coupling reactions, amine protection, desilylation and amine reduction. Some products of the multicomponent reaction underwent further detosylation and Suzuki coupling.
View Article and Find Full Text PDFRh(III)-Catalyzed C-H Annulation of Sulfoxonium Ylides and 1,3-Diynes: A Rapid Access to Alkynyl-1-Naphthol Derivatives.
Chem Asian J
April 2023
Department of Process Chemistry, National Institute of Pharmaceutical Education and Research (NIPER), Hyderabad, 500 037, Telangana, India.
An effective redox-neutral strategy to synthesize aryl/alkynyl and alkyl/alkynyl substituted 1-naphthol derivatives has been efficaciously developed by Rh(III)-catalyzed [4+2]-annulation of sulfoxonium ylides and 1,3-diynes with excellent regio- and chemoselectivity. Subsequently, the same strategy was extended to furnish various unsymmetrical binaphthol motifs in one-pot manner. Interestingly, the TMS-derived 1,3-diyne predominantly delivered the 3-alkynyl-1-naphthol via desilylation pathway.
View Article and Find Full Text PDFA Stereocontrolled Total Synthesis of Lipoxin B4 and its Biological Activity as a Pro-Resolving Lipid Mediator of Neuroinflammation.
Chemistry
June 2022
Centre for Medicinal Chemistry and Drug Discovery, Krembil Research Institute, University Health Network, Toronto, Ontario, Canada.
Two stereocontrolled, efficient, and modular syntheses of eicosanoid lipoxin B4 (LXB ) are reported. One features a stereoselective reduction followed by an asymmetric epoxidation sequence to set the vicinal diol stereocentres. The dienyne was installed via a one-pot Wittig olefination and base-mediated epoxide ring opening cascade.
View Article and Find Full Text PDF[Development of New Synthetic Methods for Carbazole Compounds Aimed at Drug Discovery and Exploratory Research on Pharmaceutical Materials].
Yakugaku Zasshi
January 2022
Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University.
We are developing the synthesis of biologically interesting carbazole compounds, including natural products by tandem cyclic reactions. In this report, we describe the new synthesis of carbazole-1,4-quinones as follows; 1) the synthesis of carbazole-1,4-quinones using a tandem ring closing metathesis (RCM) -dehydrogenation reaction, 2) a novel one-pot synthesis of carbazole-1,4-quinone by consecutive Pd-catalyzed cyclocarbonylation, desilylation, and oxidation reactions. Two new synthetic strategies were applied to the synthesis of carbazole-1,4-quinone alkaloids and ellipticine quinones, and then the antiproliferative activity against HCT-116 and HL-60 cells of the synthesized compounds were evaluated.
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