Synthetic Methodology and Natural Product Synthesis
Department of Pharmacology, Toxicology and Therapeutic Chemistry
Faculty of Pharmacy and Food Sciences, UB
Josep Bonjoch Sesé
ORCID ID: 0000-0002-5551-6720
Tel +34 934024540
https://www.ub.edu/portal/web/dp-farmacologia/gsan
Principal investigator: • Josep Bonjoch Sesé
Researchers: • Daniel Solé Arjó • Mª Lluïsa Bennasar Félix • Faïza Diaba • Ben Bradshaw (Serra-Hunter)
PhD students: • Sergi Jansana • Arianna Amenta • Mar Saladrigas • Clàudia Marqués
Current
Research
Chemical Synthesis (Radical, Organometallic, and Catalytic Methodologies) and Natural Product Synthesis (Alkaloids and Terpenes)
The aim of our research project is to develop methods and strategies that can be applied for efficient total synthesis of different classes of products possessing interesting biological profiles. Processes involving radical chemistry, organometallic processes, and enantioselective organocatalysis are investigated. We are focused on increasing the efficiency of target molecule synthesis by minimizing the number of synthetic steps, opening new synthetic pathways, and using sustainable processes.
We are currently developing new synthetic methods based on radical reactions, using haloacetamides and alkenes as pro-radicals that can react with several types of radical acceptors (e.g. alkenes, ketones, hydrazones) to give functionalized compounds with a broad spectrum of utility. For example, these processes allow the concise preparation of polycyclic adamantane-type compounds on a gram-scale for their subsequent evaluation as a source of new organocatalysts and to check their biological activity.
In the field of organometallic chemistry, our goal is the study of carbon-carbon bond formation using Pd, Rh, and Ru reagents in search of new processes tor the preparation of complex organic heterocyclic compounds. The synthesis of 5- to 9-membered nitrogen heterocycles by means of annulation processes is based either on selective carbene-mediated C-H bond activation or domino sequences beginning with metal-catalyzed arylation of enolate-type nucleophiles.
Complex natural products are a source of potential pharmaceuticals, often acting as starting points for drug discovery, as well as being tools to learn about biologically important processes. Synthetic approaches to targeted lycopodium and daphniphyllum alkaloids are in course.
Selected
Publications
Saladrigas, M.; Bosch, C.; Saborit, G. V.; Bonjoch, J.; Bradshaw, B. Radical cyclization of alkene-tethered ketones initiated by hydrogen-atom transfer. Angewandte Chemie International Edition. 57: 182-186, 2018. doi.org/10.1002/anie.201709659
Solé, D.; Mariani, F.; Bennasar, M.-L.; Fernández, I. Palladium-catalyzed intramolecular carbene insertion into C(Sp3)-H bonds. Angewandte Chemie International Edition. 55: 6647-6470, 2016. doi.org/10.1002/anie.201602020
Solé, D.; Pérez-Janer, F.; Zulaica, E.; Guastavino, J. F.; Fernández, I. Pd-catalyzed α-arylation of sulfones in a three-component synthesis of 3-[2-(penyl/methylsulfonyl)ethyl]indoles. ACS Catalysis. 6: 1691-1700, 2016. doi.org/10.1021/acscatal.6b00027
Diaba, F.; Martínez-Laporta, Coussanes, G.; Fernández, I.; Bonjoch, J. Synthesis of the ABC fragment of calyciphylline A-type Daphniphyllum alkaloids. Tetrahedron. 71:3642-3651, 2015. doi 1.org/0.1016/j.tet.2014.11.044
Bradshaw, B.; Lique-Corredera, C.; Bonjoch, J. A gram-scale route to phlegmarine alkaloids: rapid total synthesis of (-)-cermizine B. Chemical Communications. 50: 7077-7206, 2014. doi.org/10.1039/c4cc01708k
Selected
Publications
Author
Identification
Saladrigas M.; Bosch, C.; Saborit, G. V. Saborit,; Bonjoch, J.; Bradshaw, B. Radical cyclization of alkene-tethered ketones initiated by hydrogen-atom transfer. Angew. Chem. Int. Ed. 57: 182-186, 2018. doi 10.1002/anie.201709659
[/su_spoiler] [su_spoiler title="" open="no" style="default" icon="plus" anchor="" class="selected-publications-toggle"]
Author
Identification
Solé, D.; Mariani, F.; Bennasar, M.-L.; Fernández, I. Palladium-catalyzed intramolecular
carbene insertion into C(Sp3)-H bonds. Angew. Chem. Int. Ed. 55: 6647-6470, 2016. doi 10.1002/anie.201602020
[/su_spoiler] [su_spoiler title="" open="no" style="default" icon="plus" anchor="" class="selected-publications-toggle"]
Author
Identification
Solé, D.; Pérez-Janer, F.; Zulaica, E.; Guastavino, J. F.; Fernández, I. Pd-catalyzed a-arylation of sulfones in a three-component synthesis of 3-[2-(penyl/methylsulfonyl)ethyl]indoles. ACS Catalysis 6: 1691-1700, 2016. doi 10.1021/acscatal.6b00027
[/su_spoiler] [su_spoiler title="" open="no" style="default" icon="plus" anchor="" class="selected-publications-toggle"]
Author
Identification
Diaba, F.; Martínez-Laporta, Coussanes, G.; Fernández, I.; Bonjoch, J. Synthesis of the ABC fragment of calyciphylline A-type Daphniphyllum alkaloids. Tetrahedron 71:3642-3651, 2015. doi 1 0.1016/j.tet.2014.11.044
[/su_spoiler] [su_spoiler title="" open="no" style="default" icon="plus" anchor="" class="selected-publications-toggle"]
Author
Identification
Bradshaw, B.; Lique-Corredera, C.; Bonjoch, J. A gram-scale route to phlegmarine alkaloids: rapid total synthesis of (-)-cermizine B. Chem. Commun. 50: 7077-7206, 2014. doi 10.1039/c4cc01708k
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