June 2018
Latest Research Outputs

Synthesis of apocarotenoids by acyclic cross metathesis and characterization as substrates for human retinaldehyde dehydrogenases

Tetrahedron

 

A new synthesis of three apocarotenoids, namely 14′-apo-β-carotenal, 12′-apo-β-carotenal and 10′-apo-β-carotenal, has been achieved that is based on the acyclic cross-metathesis of the hexaene derived from retinal and the corresponding partners. These compounds can be enzymatically converted to their carboxylic acids by the human aldehyde dehydrogenases involved in retinaldehyde oxidation. Their kinetic parameters suggest that these enzymes might play a role in the physiological metabolism of apocarotenoids.

October 2017
Latest Research Outputs

On the regiochemical differences between Pd-catalyzed heterocyclization–allylation and –arylation reactions of alkynylbenzamides: preparation of 4-allyl-isochromen-1-imines and computational study

Organic & Biomolecular Chemistry

 

The Pd(0)-catalyzed cyclization–allylation reactions of 2-alkynylbenzamides proceed with high regioselectivity to afford the 6-endo-cyclization-derived products 4-allyl-isochromen-1-imines. DFT calculations have been performed on this and the related arylation reaction, that has been reported to afford the products corresponding to an exo-cyclization under similarly Pd(0)-catalyzed conditions. Under the reaction conditions, these cyclizations are presumed to be triggered by activation of the C–C triple bond with either an allyl- or an aryl palladium complex, generated by oxidative addition of an allyl- or aryl halide to the Pd(0) catalyst. For reactions promoted by allylpalladium species, calculations predict a reversible cyclization, followed by a regioselectivity-determining endo-selective reductive elimination. In contrast, according to calculations, the corresponding arylations would proceed through irreversible exo-selective cyclization and reductive elimination steps. These predictions are consistent with the experimental observations. The divergent regiochemical outcome appears to have its origin in the differences caused on the intermediate palladium complexes by the groups derived from the coupling agents (allyl or aryl) and by the reaction conditions (solvent and ligands) through a subtle interplay of polarity and coordinative effects.

October 2017
News

Great moments!

Great moments!

Susana, Adrián, Sheila, Miguel and María

Susana, Adrián, Sheila, Miguel and Maria, it has been a pleasure having these good students doing their degree project. And what to say of those smiles!

October 2017
Latest Research Outputs

Mass Spectrometry of Algal Chlorophyll c Compounds

In this article we review the application of direct and tandem mass spectrometry techniques to the analysis of acidic and esterified chlorophylls c, summarize their fragmentation patterns and enumerate some experimental fragmentation rules for their identification.

October 2017
Latest Research Outputs

Total synthesis of naturally occurring (+)-psychotriasine and the related...

October 2017
Latest Research Outputs

Indole–Indole Ullmann Cross-Coupling for CAr–N Bond Formation: Total Synthesis of (–)-Aspergilazine A

October 2017
Latest Research Outputs

Synthesis of the octahydronaphthalene core of nahuoic acid A via a B(C6F5)3-catalyzed intramolecular Diels–Alder (IMDA) reaction

September 2017
Latest Research Outputs

Rearrangement of vinyl allene oxide geometric isomers to cyclopentenones. Further computational insights with biologically relevant model systems

September 2017
Latest Research Outputs

Lineage-specific duplication of amphioxus retinoic acid degrading enzymes (CYP26) resulted in sub-functionalization of patterning and homeostatic roles

September 2017
Latest Research Outputs

Natural and structure-based RXR ligand scaffolds and their functions