Francisco M. Guerra

Universidad de Cádiz

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F. Javier Moreno‐Dorado

Universidad de Cádiz

Guillermo M. Massanet

Universidad de Cádiz

Zacarı́as D. Jorge

Universidad de Cádiz

Giovanni De Munno

University of Calabria

Donatella Armentano

University of Calabria

Ana Leticia García‐Cabeza

Universidad de Cádiz

Marı́a J. Ortega

Universidad de Cádiz

F. Lloret

Rubén Marín‐Barrios

Universidad de Cádiz

Juan J. Rubal

Universidad de Cádiz

Cooperative Institutions

Universidad de Cádiz

University of Illinois Urbana-Champaign

Hospital Universitario Puerto Real

Universidad de La Laguna

Université Hassan II Mohammedia

Universitat de València

Urbana University

University of Córdoba

Centre National de la Recherche Scientifique

Los Alamos National Laboratory

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Phenylpropanoids from Thapsia transtagana

Phytochemistry (2006)

Abderrahmane Saouf Francisco M. Guerra Juan J. Rubal Zacarı́as D. Jorge Mohamed Akssira

10.1016/j.phytochem.2006.01.032

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Citations (7)

Multivariate optimization of the Kharasch–Sosnovsky allylic oxidation of olefins

Tetrahedron (2011)

Rubén Marín‐Barrios Francisco M. Guerra Ana Leticia García‐Cabeza F. Javier Moreno‐Dorado Guillermo M. Massanet

Alkene

Limiting

10.1016/j.tet.2011.11.083

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Citations (20)

DoE (Design of Experiments) Assisted Allylic Hydroxylation of Enones Catalysed by a Copper–Aluminium Mixed Oxide

European Journal of Organic Chemistry (2013)

Ana Leticia García‐Cabeza Rubén Marín‐Barrios Redouan Azarken F. Javier Moreno‐Dorado Marı́a J. Ortega

Abstract The allylic hydroxylation of enones using dioxygen as the oxidant has been studied. The reaction was first examined in the absence of any catalyst, using β‐ionone as a model substrate. Then a new copper–aluminium mixed oxide, Cu–Al Ox, was prepared and characterized in order to be used as a catalyst. This oxide showed good activity, and provided the corresponding γ‐ or ϵ‐hydroxylated enones, starting from different α,β‐ or α,β,γ,δ‐unsaturated ketones. In all cases, the yields were significantly improved compared to experiments run in the absence of the catalyst. The reaction was selective, and the formation of epoxides or other overoxidation products was detected only to a minor extent. The described procedure is a technically straightforward synthetic alternative to those methods described to date involving many reaction steps or toxic reagents. The reactions were optimized using design of experiments techniques (DoE).

Hydroxylation

Copper oxide

10.1002/ejoc.201301145

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Citations (50)

Meaning of oxygen consumption by the myocardium and of the enzymatic release of phosphors regarding the mechanism of digital action.

PubMed (1947)

Francisco M. Guerra

Consumption

Mechanism of Action

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CCDC 293570: Experimental Crystal Structure Determination

The Cambridge Structural Database (2006)

Donatella Armentano Giovanni De Munno Francisco M. Guerra Miguel Julve F. Lloret

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

10.5517/cc9vh0m

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Enantioselective Synthesis of Arylmethoxyacetic Acid Derivatives.

ChemInform (2003)

F. Javier Moreno‐Dorado Francisco M. Guerra Marı́a J. Ortega Eva Zubı́a Guillermo M. Massanet

Abstract For Abstract see ChemInform Abstract in Full Text.

10.1002/chin.200325109

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Copper-Catalyzed Microwave-Expedited Oxyphosphorylation of Alkynes with Diethyl Phosphite and t-Butyl Hydroperoxide Synthesis of Densely Functionalized Phosphonylated Indenones

The Journal of Organic Chemistry (2021)

Pablo Macías-Benítez Alfonso Sierra-Padilla M. Jimenez-Tenorio F. Javier Moreno‐Dorado Francisco M. Guerra

Treatment of alkynes with diethyl phosphite and t-butyl hydroperoxide in the presence of [Cu(MeCN)4]BF4 under microwave irradiation produced the oxyphosphorylation of the triple bond, giving rise to the corresponding β-ketophosphonates in moderate-to-good yields. When the triple bond was conjugated to a carbonyl group bearing an aromatic ring, it led to the cyclization of the resulting ketone intermediate, producing eventually different phosphonylated indenones.

Triple bond

10.1021/acs.joc.1c01763

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Citations (6)

Inhibition of the 4Fe–4S proteins IspG and IspH: an EPR, ENDOR and HYSCORE investigation

Chemical Science (2014)

Francisco M. Guerra Ke Wang Jikun Li Weixue Wang Yi-Liang Liu

IspG and IspH are proteins that are involved in isoprenoid biosynthesis in most bacteria as well as in malaria parasites and are important drug targets. They contain cubane-type 4Fe-4S clusters that are involved in unusual 2H+/2e- reductions. Here, we report the results of electron paramagnetic resonance spectroscopic investigations of the binding of amino- and thiolo-HMBPP (HMBPP=E-1-hydroxy-2-methyl-but-2-enyl 4-diphosphate) IspH substrate-analog inhibitors to both proteins, as well as the binding of HMBPP and an acetylene diphosphate inhibitor, to IspG. The results show that amino-HMBPP binds to reduced IspH by Fe-C π-bonding with the olefinic carbons interacting with the unique 4th Fe in the 4Fe-4S cluster, quite different to the direct Fe-N ligation seen with the oxidized protein. No such π-complex is observed when amino-HMBPP binds to reduced IspG. No EPR signal is observed with IspH in the presence of dithionite and thiolo-HMBPP, suggesting that the 4Fe-4S cluster is not reduced, consistent with the presence of a 420 nm feature in the absorption spectrum (characteristic of an oxidized cluster). However, with IspG, the EPR spectrum in the presence of dithionite and thiolo-HMBPP is very similar to that seen with HMBPP. The binding of HMBPP to IspG was studied using hyperfine sublevel correlation spectroscopy with 17O and 13C labeled samples: the results rule out direct Fe-O bonding and indicate π-bonding. Finally, the binding to IspG of a potent acetylene diphosphate inhibitor was studied by using electron-nuclear double resonance spectroscopy with 13C labeled ligands: the large hyperfine couplings indicate strong Fe-C π-bonding with the acetylenic group. These results illustrate a remarkable diversity in binding behavior for HMBPP-analog inhibitors, opening up new routes to inhibitor design of interest in the context of anti-bacterial and anti-malarial drug discovery, as well as "cubane-type" metallo-biochemistry, in general.

10.1039/c3sc53301h

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Citations (16)

Me 3 SiCHN 2 の不斉双極子状環化付加新種のアミノ酸の合成:アザプロリン

Journal of the American Chemical Society (1997)

Michael Mish Francisco M. Guerra Erick M. Carreira

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ChemInform Abstract: Copper‐Catalyzed Oxidation of Alkenes and Heterocycles

ChemInform (2016)

Ana Leticia García‐Cabeza F. Javier Moreno‐Dorado Marı́a J. Ortega Francisco M. Guerra

Abstract Review: [90 refs.

10.1002/chin.201642225

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