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1. A solid-phase version of the palladium-catalyzed carbonyl allylation by allylic alcohols with SnCl2

Author

Antonio Delgado, Amadeu Llebaria, and Lydia Carde

Subjects
Allylic rearrangement, Chemistry, organic chemicals, Phase (matter), Organic Chemistry, Drug Discovery, food and beverages, chemistry.chemical_element, Organic chemistry, Solvent effects, Biochemistry, Catalysis, Palladium
Abstract

A solid-phase version of the palladium-catalyzed carbonyl allylation of aldehydes by allylic alcohols is described. Preliminary studies have been carried out with resin bound aldehydes 1a–c and different allylic alcohols. Solvent effects as well as the regio- and diastereoselectivity of our solid-phase conditions are compared with solution-phase protocols.

Published
2001

2. PaaSicats: Powerful catalysts for asymmetric epoxidation of enones. Novel syntheses of α-arylpropanoic acids including (S)-fenoprofen

Author

Lydia Carde, Thomas Geller, Stanley M. Roberts, and Huw M. L. Davies

Subjects
chemistry.chemical_classification, Fenoprofen, Ketone, Organic Chemistry, Enantioselective synthesis, Biochemistry, Catalysis, chemistry.chemical_compound, chemistry, Drug Discovery, medicine, Organic chemistry, Moiety, Trimethylaluminium, Oxidative cleavage, Dichloromethane, medicine.drug
Abstract

Application of the recently developed silica-adsorbed polyleucine catalysts to the enantioselective epoxidation of two enones is reported. Treatment of these epoxides with trimethylaluminium in moist dichloromethane generates the α-hydroxy-β-methyl-ketones, with inversion of configuration. Diastereoselective reduction of the ketone moiety followed by oxidative cleavage generates α-arylpropanoic acids.

Published
1999

3. ChemInform Abstract: PaaSicats: Powerful Catalysts for Asymmetric Epoxidation of Enones. Novel Syntheses of α-Arylpropanoic Acids Including (S)-Fenoprofen

Author

Lydia Carde, Thomas Geller, Stanley M. Roberts, and Huw M. L. Davies

Subjects
chemistry.chemical_classification, Fenoprofen, Ketone, Chemistry, Enantioselective synthesis, General Medicine, Combinatorial chemistry, Catalysis, chemistry.chemical_compound, medicine, Moiety, Oxidative cleavage, Trimethylaluminium, medicine.drug, Dichloromethane
Abstract

Application of the recently developed silica-adsorbed polyleucine catalysts to the enantioselective epoxidation of two enones is reported. Treatment of these epoxides with trimethylaluminium in moist dichloromethane generates the α-hydroxy-β-methyl-ketones, with inversion of configuration. Diastereoselective reduction of the ketone moiety followed by oxidative cleavage generates α-arylpropanoic acids.

Published
2010

4. Solid-phase synthesis of a combinatorial library of dihydroceramide analogues and its activity in human alveolar epithelial cells

Author

Amadeu Llebaria, Lydia Carde, Antonio Delgado, Josefina Casas, Rosalia Pascual, Daniel Canals, Obdulia Rabal, Gemma Villorbina, Jordi Teixidó, Gemma Fabriàs, and Santiago Grijalvo

Subjects
Ceramide, Analogues, Stereochemistry, Clinical Biochemistry, Drug Evaluation, Preclinical, Pharmaceutical Science, Apoptosis, Ceramides, Biochemistry, Sensitivity and Specificity, Sphingolipid, Cell Line, chemistry.chemical_compound, Solid-phase synthesis, Growth arrest, Drug Discovery, Combinatorial Chemistry Techniques, Humans, COPD, Molecular Biology, Cell Proliferation, Binding Sites, Dose-Response Relationship, Drug, Molecular Structure, Dihydroceramide, Organic Chemistry, Cell Cycle, Diastereomer, Epithelial Cells, Stereoisomerism, Flow Cytometry, Combinatorial, Pulmonary Alveoli, chemistry, Drug Design, Molecular Medicine
Abstract

13 páginas,4 tablas, 1 esquema., Solid-phase synthesis of a small combinatorial library of dihydroceramide analogues as mixtures of erythro and threo diastereomers is described. Some dihydroceramide analogues cause growth arrest and apoptosis in a dose-dependent manner in human alveolar epithelial cells. This activity is likely due to the threo isomers, as evidenced by cellular studies with a pair of diastereomerically pure N-acyldihydrosphingosines. The apoptotic activity reported in this work provides information for the design of new compounds that may provide the basis for the generation of biochemical tools for the study of different pathologies where ceramide and/or dihydroceramide are involve., Financial support from European Union (contract FMRXCT98-0235), Ministerio de Ciencia y Tecnología Spain (Projects MCYT BQU2002-03737 and MCYT CTQ2005-00175/BQU), Fondos Feder (EU), Fundación. La Marató de TV3 (Projects UB-040730 and CSIC- 040731) and Generalitat de Catalunya (2005SGR01063) is acknowledged. S. G. and O. R. acknowledge the CSIC and Generalitat de Catalunya, respectively, for predoctoral fellowships.

Published
2007

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