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Straightforward methodology for the enantioselective synthesis of benzo[a]- and indolo[2,3-a]quinolizidines.
An enantioselective two-step route to substituted benzo[a]- and indolo[2,3-a]quinolizidines has been developed and takes advantage of the masked N-acyl iminium ion present in the resulting oxazolopiperidone lactams.
Enantioselective spirocyclizations from tryptophanol-derived oxazolopiperidone lactams.
- M. Amat, Maria M. M. Santos, Antonia M Gómez, D. Jokic, E. Molins, J. Bosch
- ChemistryOrganic letters
- 29 June 2007
A straightforward synthetic route to enantiopure spiro[indole-3,3'-indolizidines] is reported. The key step is a Lewis acid promoted cyclization of a Na-tosyltryptophanol-derived oxazolopiperidone…
A metabolomic approach differentiates between conventional and organic ketchups.
- A. Vallverdú-Queralt, A. Medina-Remón, Isidre Casals-Ribes, M. Amat, R. Lamuela-Raventós
- Chemistry, MedicineJournal of agricultural and food chemistry
- 11 October 2011
It was found that organic cultivation was found to provide tomatoes and tomato-derived products with a significantly higher content of antioxidant microconstituents, whereas glutamylphenylalanine and N-malonyltryptophan were detected only in conventional ketchups.
Cyclocondensation Reactions between 2-Acyl-3-indoleacetic Acid Derivatives and Phenylglycinol: Enantioselective Synthesis of 1-Substituted Tetrahydro-β-carboline Alkaloids
Cyclocondensation reactions between a variety of 2-acyl-3-indoleacetic acid derivatives and (R)-phenylglycinol were studied. Successful results were obtained from N-alkyl keto acid derivatives. The…
Synthesis and biological evaluation of 2-phenylpyran-4-ones: a new class of orally active cyclooxygenase-2 inhibitors.
The in vivo antiinflammatory activity of these compounds was confirmed with the evaluation of their antiarthritic and analgesic effectiveness and their pharmacokinetic profile in rats is compatible with a once a day administration by oral route in humans.
On the origin of the stereoselectivity in the alkylation of oxazolopiperidone enolates.
- Ignacio Soteras, Ó. Lozano, F. J. Luque
- Chemistry, BiologyJournal of the American Chemical Society
- 27 April 2006
The origin of the diastereoselective alkylation of enolates of oxazolopiperidones is studied by means of theoretical calculations and experimental assays and it is found that the intramolecular hydrogen bond formed between the phenyl ring and the carbonyl oxygen in the enolate largely reduces the difference in stability of the two TSs compared to the unsubstituted oxazolate.
Straightforward Methodology for the Enantioselective Synthesis of Benzo[a]- and Indolo[2,3-a]quinolizidines.
Enantioselective Formal Synthesis of ent-Rhynchophylline (I) and ent-Isorhynchophylline (II).
Chiral oxazolopiperidone lactams: versatile intermediates for the enantioselective synthesis of piperidine-containing natural products.
Of particular interest are cyclocondensation reactions with racemic or prochiral delta-oxo (di)acid derivatives in processes involving dynamic kinetic resolution and/or differentiation of enantiotopic or diastereotopic ester groups, as they directly lead to lactams that already incorporate the carbon substituents on the heterocyclic ring.