Group of Synthesis of Natural Azapolycycles

Laboratori de Química Orgànica, Facultat de Farmàcia, Universitat de Barcelona

Joan XXIII s/n, 08028-Barcelona (SPAIN)

934 024 540

josep.bonjoch@ub.edu

Prof. Josep Bonjoch, Full Professor UB

Dr. Faïza Diaba, Associate Professor

Dr. Ben Bradshaw, Assistant Professor

Claudio Parra                       Gisela Saborit

Juan Montiel                         Guilhem Coussanes

Caroline Bosch                   Sergi Jensana

Total synthesis of natural products

Organocatalysis

Radicals in C-C bond formation

Synthetic Methodology

 

 

1. Diaba, F.; Pujol-Grau, C.; Martínez-Laporta, A.; Fernández, I.; Bonjoch, J.

Org. Lett. 2015, 17, 568-571

Synthesis of the tetracyclic ABCD ring systems of madangamines D-F

 

2. Bürki, C.; Bonjoch, J.; Bradshaw, J.; Villa, G.; Renaud, P.

Chem. Eur. J. 2015, 21, 395-401.

Total synthesis of aignopsanes, a class of sesquiterpenes: (+)-aignopsanoic acid A, (-)-Methyl Aignopsanoate A, and (-)-Isoaignopsanoic A

 

3. Bradshaw, B.; Luque-Corredera, C.; Bonjoch, J.

Chem. Commun. 2014, 50, 7099-7102

A gram-scale route to phlegmarine alkaloids: rapid total synthesis of (-)-cermizine B

 

4. Bradshaw, B.; Luque-Corredera, C.; Saborit, G.; Cativiela, C.; Dorel, R.; Bo, C.; Bonjoch, J.

Chem. Eur. J. 2013, 19, 13881

Synthetic and DFT studies towards a unified approach to phlegmarine alkaloids: aza-Michael intramolecular processes leading to 5-oxodecahydroquinolines

 

5. Bradshaw, B.; Luque-Corredera, C.; Bonjoch, J.

Org. Lett. 2013, 15, 326

cis-Decahydroquinolines via asymmetric organocatalysis: application to the total synthesis of lycoposerramine Z

 

6. Diaba, F.; Martínez-Laporta, A.; Bonjoch, J.; Pereira, A.; Muñoz-Molina, J. M.; Pérez, P. J. Belderrain, T. R.

Chem. Commun. 2012, 48, 8799

Cu(I)-catalyzed atom transfer radical cyclization of trichloroacetamides tethered to electron-deficient, -neutral, and –rich alkenes: synthesis of polyfunctionalized 2-azabicyclo[3.3.1]nonanes

 

7. Diaba, F.; Bonjoch, J.

NMR evidence of the kinetic and thermodynamic products in the NIS promoted cyclization of 1-phenyl-4-pentenylamines. Synthesis and reactivity of trans-2-phenyl-5-iodopiperidines

Chem. Commun. 2011, 47, 3251-3253

 

8. Bradshaw, B.; Etxebarria-Jardí, G.; Bonjoch, J.

 J. Am. Chem. Soc. 2010, 132, 5966.

Total Synthesis of (-)-Anominine

 

9. Bradshaw, B.; Etxebarria-Jardí, G.; Bonjoch, J.; Viózquez, S. F.; Guillena, G.; Nájera, C.

Adv. Synth. Catal. 2009, 351, 2482-2490

Efficient Solvent-free Robinson annulation protocols for the highly enantioselective synthesis of the Wieland-Miescher ketone and analogues

 

10. Quirante, J.; Paloma, Diaba, F.; Vila, X.; Bonjoch, J.

J. Org. Chem. 2008, 73, 768-771.

Synthesis of diazatricyclic core of madangamines from cis-perhydroisoquinolines

 

 

Past and present collaborations with other groups                                                                                Collaborative Projects with Prof. Clayden (Manchester), Carmeli (TelAviv), Cossy (Paris), Hertweck (Jena), Osborn (Reading), Nájera (Alicante), P. J. Pérez (Huelva), Cativiela (Zaragoza), Renaud (Bern), Cuerva (Granada)

 

Josep Bonjoch was born in Barcelona (Catalonia, Spain) in 1952. He received his Ph.D. degree (1979) under the supervision of Prof. Joan Bosch at the University of Barcelona, Faculty of Chemistry. He then moved to the Faculty of Pharmacy at the same University, where he was promoted to Associate Professor (1984) and subsequently became Full Professor of Organic Chemistry in 1992. His main research involves the synthesis of complex nitrogen-containing natural products, as a motive for developing new synthetic methodology.

He has described for the first time the total synthesis of seventeen natural products such as indole alkaloids  (melinonine, echitamidine inter alia), some aeruginosin-type peptides, and terpenes (nakamurol, xylarenal A, and anominine), and lycopodium alkaloids (cermizine B).

The main methodological areas in which his group is involved are organocatalysis and radical chemistry

He has author of more than 145 papers and three book chapters.

Supervisor of 27 Ph Ds  and 5 in course.

Visiting Professor at the Université de Bordeaux (2006).

Main research of 7 Competitive Projects from 1993 until the present from the Spanish Government.

Group Leader in the “Expanding Capability in Heterocyclic Organic Synthesis” (ECHONET) Marie Curie Activity-Initial Training Network (ITN) 2013-2016: FP7 Seventh Framework Programme of European Commission

21st Postgraduate Heterocyclic Symposium: AstraZeneca, Loughborough (2006)

XII Semana Científica « Antonio González », La Laguna (2008)

17th Fèlix Serratosa Conference , ICIQ-Tarragona (2012)

Invited Conferences (2004-2014) Gif-sur-Yvette-CNRS, Palaiseau-Polytechnique, Alicante (2004), Lugo-RSEQ (2005), Manchester, IECB-Pessac, Santorini-COST (2006), Granada (2007), Buenos Aires (2008), A Coruña, UJI-Castelló, La Palma (2009),  CINVESTAV-México DF, UNAM-México DF, Cuernavaca, Puebla (2010), UZAR-Zaragoza (2011), Izmir-COST, Santander-RSEQ (2013) Bern, San Sebastián, Almería (2014)