Professor Josep Bonjoch was born in Barcelona (Catalonia, Spain) in 1952.
He obtained his Ph.D. in Chemistry from the University of Barcelona (1979),
where he went on to become an Associate Professor of Organic Chemistry (1984)
and was promoted to Full Professor in 1992. Author of more than 115 papers,
his main research involves the synthesis of natural products and the development
of synthetic methods using radical and organometallic species.
The “Synthesis
of Natural Azapolicycles” research group of the University
of Barcelona, founded by the MEC (CTQ2004-04701/BQU),
has considerable experience in organic synthesis, especially
in the field of natural product synthesis (alkaloids,
peptides and terpenoids), which in the last five years
(June 2001-October2006) has been reflected in the following:
The GSAN research group is formed by 11 researchers (one full professor,
one assistant professor, one lecturer, one associate professor, one Juan de la Cierva researcher,
three post-doctoral researchers under contract and three students with their own grants).
The research group receives financial support from DGR (Generalitat de Catalunya 2005SGR-00442)
as a consolidated group.
Conferences given during the last five years by the director of the research group at
the Universities of Geneva, Neuchâtel, Fribourg, Bern, René Descartes (ParisV), Valencia,
Ecole Polytechnique de Palaiseau (Paris), Manchester, Bordeaux and at the research centers
of CSIC (Madrid), CNRS (Gif-sur-Yvette), and Institut European of Chemistry and Biologie
(IECB) at Bordeaux.
Oral communications at the 7th International Symposium in Carbanion Chemistry (ISCC-7),
Alicante, 2004; 1st European Chemistry Congress, Budapest, 2006
Invited Conference at the XXX Runión Bienal de Química, Lugo, 2005; RSC-Hetrocyclic Symposium
(Astra Zeneca) Loughborough 2006; Midterm Evalutation Meeting COST Action D28, Santorini (Grece) 2006;
Journées de Chimie Organique (JCO 2007), Palaiseau (France).
* Over the period June-2001 to September-2006, the research group has described the first total
synthesis of six natural products belonging to several structural types: the peptides of
aquatic origin aeruginosins 298-A and B (1), microcin SF608 (5) and aeruginosin EI461 (7),
the marine diterpenoid nakamurol A (9) and the fungal sesquiterpenoid xylarenal A (15).
In all cases, the synthesis has allowed the determination of the absolute configuration of these
compounds and it has been shown that the structures for the three aeruginosins were putative.
*In the course of the research work several synthetic general procedures were established:
(a) Carbociclyzation of aryl and vinyl halides upon ketone enolates (3,4,7,9,12) and related species (nitroderivatives, esters and nitriles) (17), catalyzed by Pd. This procedure constitutes the key step in the synthetic approaches to FR901483 (11) and other alkaloids (17).
(b) Synthesis of decahydroisoquinolines, through radical cyclization of trichloroacetamides upon enones, of interest in the field of madangamine synthesis (13) and synthesis of enantiopure decahydroquinolines of interest for the lepadin synthesis (16,19,20).
(c) Normorphan síntesis by a decarbonylative cyclization of aminoseleno esters promoted by tributyltin hydride upon electronically poor alkenes (4)
(d) Synthesis of enantiopure octahydroindoles from Birch reduction of tyrosine derivatives followed by an aminocyclization process leading to bicyclic analogues of proline (1,7). These compounds have allowed the first synthesis of non-proteinogenic ?-amino acids L- Choi, L-Ccoi and other stereoisomers, all of them in their enantiopure form, which constitute the bicyclic core of aeruginosins, a new type of peptides isolated from cyanobacteria showing activity as thrombin inhibitors (1,6,8,18).
(e) Synthetic applications of the Piers decalone in its enantiopure form to the synthesis of terpenoids, such as nakamurol and xylarenal A (10,15).
1. Valls,N.; López-Canet, M.; Vallribera, M.; Bonjoch, J.
Chem. Eur. J. 2001, 7, 3446-3460
First total syntheses of aeruginosin 298-A and aeruginosin 298-B based on a stereocontrolled entry to the new amino acid 2-carboxy-6-.. indole
2. Solé, D.; García-Rubio, S.; Vallverdú, L.; Bonjoch, J.
J. Org. Chem. 2001, 66, 5266-5268
A straightforward synthetic entry to the 4,9b-propanopyrrolo[2,3-c]quinoline system by a new reductive cyclization of ?'-(2-nitrophenyl)enone
3. Solé, D., Vallverdú, L.; Bonjoch, J.
Adv. Synth. Catal. 2001, 343, 439-442
Palladium-catalyzed intramolecular coupling of aryl halides and ketone enolates: synthesis of hexahydro-2,6-methano-1-benzazocines.
4. Solé, D.; Vallverdú, L.; Peidró, E.: Bonjoch, J.
J. Chem. Soc. Chem. Commun. 2001, 1888-1889
Palladium-catalysed intramolecular annulation of 2-haloanilines and ketones: enolate arylation vs nucleophilic addition to the carbonyl group.
5. Quirante, J.; Vila, X.; Escolano, C..; Bonjoch, J.
J. Org. Chem. 2002, 67, 2323-2328
Decarbonylative radical cyclization of ?-amino selenoesters upon electrophilic alkenes. A general method for the 6-azabicyclo[3.2.1]octane.
6. Valls, N.; Vallribera, M.; López-Canet, M.; Bonjoch, J.
J. Org. Chem. 2002, 67, 4945-4950
Synthesis of microcin SF608
7. Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J.
J. Am. Chem. Soc. 2003, 125, 1587-1594
Intramolecular Pd-mediated processes of amino-tethered aryl halides and ketones: insight into the ketone ?-arylation and carbonyl-addition….
8. Valls, N.; Vallribera, M.; Carmeli, S.; Bonjoch, J.
Org. Lett. 2003, 5, 447-450
Synthesis of both the putative and revised structures of aeruginosin EI461 bearing a new bicyclic ?-amino acid
9. Solé, D.; Diaba, F.; Bonjoch, J.
J. Org. Chem. 2003, 68, 5746-5749
Nitrogen heterocycles by pallasium-catalyzed cyclization of amino-tethered vinyl halides and ketone enolates
10. Díaz, S.; Cuesta, J.; González, A.; Bonjoch, J.
J. Org. Chem. 2003, 68, 7400-7406
Synthesis of (-)-nakamurol A and assignment of absolute configuration of diterpenoid (+)-nakamurol
11. Bonjoch, J,; Diaba, F.; Puigbó, G.; Peidró, E.; Solé, D.
Tetrahedron Lett. 2003, 44, 8387-8390
A new synthetic entry to the trocyclic skeleton of FR901483 by palladium-catalyzed cyclization of vinyl bromides with ketone enolates
12. Solé, D.; Vallverdú, L.; Solans, X.; Font-Bardía, M.; Bonjoch, J.
Organometallics 2004, 23,
1438-14471
Synthesis and reactivity of four-membered azapalladacycles derived from N,N-dialkyl-2-iodoanilines: insertion reactions of carbenes into the C-Pd.
13. Vila, X.; Quirante, J.; Paloma, L.; Bonjoch, J.
Tetrahedron Lett. 2004, 45, 4661-4664.
Six-membered nitrogen ring formation by radical cyclization of trichloroacetamides with enones. A synthetic entry to cis-perhydroisoquinoline-3,6-di
14. Solé, D.; Urbaneja, X..; Bonjoch, J.
Adv. Synth. Catal. 2004 , 346, 1646-1650.
Palladium-catalyzed intramolecular coupling of amino-tethered vinyl halides with ketones, esters, and nitriles using potassium phenoxide as the base
15. Díaz, S.; González, A.; Bradshaw, B.; Cuesta, J.; Bonjoch, J.
J. Org. Chem. 2005, 70, 3749-3752.
Enantioselective syntheses of (+)-xylarenal A and ent-xylarenal A
16. Mena, M; Bonjoch, J.
Tetrahedron 2005, 61, 8264-8270.
Model studies in the lepadin series: synthesis of enantiopure decahydroquinolines by aminocyclization of 2.(3-aminoalkyl)cyclohexenones
17. Solé, D.; Urbaneja, J.; Bonjoch, J.
Org. Lett. 2005, 7, 5461-5464
Synthesis of the 4-azatricyclo[5.2.2.04,8]undecan-10-one core of Daphniphyllum alkaloid calyciphylline A using a Pd-catalyzed enolate alkenylation
18. Valls, N.; Borregán, M.; Bonjoch, J.
Tetrahedron Lett. 2006, 47, 3701-3705.
Synthesis of ?-chloro ?-amino acids: (2S,3R). and (2S,3S)-3-chloroleucine
19. Mena, M; Valls, N.; Borregán, M.; Bonjoch, J.
Tetrahedron 2006, 62, 9166-9173.
Synthesis of enantiopure cis-decahydroquinolines from homotyramines by Birch reduction and aminocyclization
20. Mena, M; Bonjoch, J.; Gomez Pardo, D.; Cossy, J.
J. Org. Chem. 2006, 71, 5930-5935.
Ring expansion of functionalized octahydroindoles to enantiopure cis-decahydroquinoline
