LABORATORY OF ORGANIC CHEMISTRY

Methodological Research in Heterocyclic Synthesis

The research group is involved in the construction of bioactive organic molecules using new, efficient synthetic tools. In particular, our work is concerned with the development of annulation methodologies suitable for heterocyclic substrates and their further adaptation to the synthesis of biologically active natural products and natural product-like molecules of heterocyclic nature. After having exploited the rich chemistry of dihydropyridines and pyridinium salts in the synthesis of alkaloids, the main current areas of methodological interest are the use of intramolecular radical and metal-mediated reactions.

Contact adress

• Designing new heterocyclic pro-radicals and studying the behaviour of the corresponding radicals (indolylacyl, indolyl and other derived from pentagonal heterocycles) in intramolecular processes using aza-alkenes as acceptors.
• Developing new homolytic acylation reactions on heterocyclic substrates for the synthesis of 1,4-quinone-containing natural products.
• Using ring-closing metathesis (RCM) for the elaboration of medium-sized rings as well as palladium (0)-catalyzed cyclization reactions upon alkenes.
  

Recent publications

• Bennasar, M.-L.; Zulaica, E.; Alonso, Y.; Bosch, J. Nucleophilic Addition to Chiral Pyridinium Salts. Stereoselective Synthesis of (–)-Na-Methylervitsine. Tetrahedron: Asymmetry 2003, 14, 469-479.PDF
• Bennasar, M.-L.; Roca, T.; Padullés, A. Chemoselective Radical Cleavage of Cbz-Protected Nitrogen Compounds. Org. Lett. 2003, 5, 569-572. PDF
• Bennasar, M.-L.; Zulaica, E.; Roca, T.; Alonso, Y.; Monerris, M. A Synthetic Entry to 3,5-Disubstituted Pyridines. Tetrahedron Lett. 2003, 44, 4711-4714. PDF
• Bennasar, M.-L.; Roca, T.; Monerris, M. Total Synthesis of the Proposed Structures of Indole Alkaloids Lyaline and Lyadine. J. Org. Chem. 2004, 69, 752-756.PDF
• Bennasar, M.-L.; Roca, T.; Ferrando, F. Intramolecular Reactions of 2-Indolylacyl Radicals: Access to 1,2-Fused Ring Indole Derivatives. Org. Lett. 2004, 6, 759-762.PDF
• Bennasar, M.-L.; Roca, T.; Ferrando, F. Intramolecular Reactions of 2-Indolylacyl Radicals: Cyclisation upon Aromatic Rings. Tetrahedron Lett. 2004, 45, 5605-5609.PDF
• Bennasar, M.-L.; Roca, T.; Zulaica, E.; Monerris, M. Total Synthesis of the Naphthyridine Alkaloid Jasminine. Tetrahedron 2004, 60, 6785-6789.PDF
• Bennasar, M.-L.; Zulaica, E.; Tummers, S. A Synthetic Entry to 2,3-Fused Ring Indole Derivatives by Ring-Closing Metathesis Reactions. Tetrahedron Lett. 2004, 45, 6283-6285.PDF
• Bennasar, M.-L.; Roca, T.; Monerris, M.; García-Díaz, D. Sequential N-Acylamide Methylenation–Enamide Ring-Closing Metathesis: A Synthetic Entry to 1,4-Dihydroquinolines. Tetrahedron Lett. 2005, 46, 4035-4038.PDF
• Bennasar, M.-L.; Roca, T.; Ferrando, F. Regioselective Intramolecular Reactions of 2-Indolylacyl Radicals with Pyridines: A Direct Synthetic Entry to Ellipticine Quinones. J. Org. Chem. 2005, 70, 9077-9080.PDF
• Bennasar, M.-L.; Zulaica, E.; Alonso, S. Preparation of RCM Substrates for Azepinoindole Synthesis: Reductive Amination versus Tetrahydro-gamma-Carboline Formation. Tetrahedron Lett. 2005, 46, 7881-7884.PDF
• Bennasar, M.-L.; Roca, T.; Ferrando, F. Regioselective 6-Endo Cyclizations of 2-Indolylacyl Radicals: Total Synthesis of the Pyrido[4,3-b]carbazole Alkaloid Guatambuine. J. Org. Chem. 2006, 71, 1746-1749.PDF
• Bennasar, M.-L.; Roca, T.; Ferrando, F. A New Radical-Based Route to Calothrixin B. Org. Lett. 2006, 8, 561-564.PDF
• Bennasar, M.-L.; Roca, T.; Monerris, M.; García-Díaz, D. Sequential N-Acylamide Methylenation-Enamide Ring Closing Metathesis: Construction of Benzo-Fused Nitrogen Heterocycles. J. Org. Chem. 2006, 71, 7028-7034.PDF
• Bennasar, M.-L.; Zulaica, E.; Solé, D.; Alonso, S. Facile Synthesis of Azocino[4,3-b]indoles by Ring-Closing Metathesis. Tetrahedron 2007, 63, 861-866. .PDF