Bioactive compounds and new organic materials
Our research is also focused towards the synthesis of bioactive compounds and organic materials using novel synthetic methodologies mostly developed in the group. As example, we have synthesized the natural product Neomarinone with antibiotic activity and related compounds such as fumaquinone.[1] The synthetic strategy exploited a Diels-Alder reaction using bis-1,3-silyloxydienes and stereoselective conjugate addition reactions using organometallics. In another project, we have also completed the synthesis of the antitumoral natural products Barrenazines.[2] In this case the synthetic strategy combines novel methodologies such as methatesis reaction, allylic borylation and a reductive dimerization reaction.
More recently, the palladium-catalyzed cross-coupling reactions with triorganoindium reagents discovered in the group, was used for the synthesis of natural product Hyrtinadine and biologically active Neurodazine.[3] This methodology was also used for the synthesis of substituted pyrimidines and imidazoles of pharmacological interest which activity is being evaluated.
Actually, our methodology is being applied to the synthesis of novel organic materials such as dithienylethenes (molecular stwichers), oligothiophenes and π-conjugated systems (push-pull) of interest in materials science.[4] Our methodology is being applied to the synthesis of novel organic materials such as 1,2-dithienylethenes (DTEs) with a maleimide bridge as photochemical stwichers.[5] We also carried out the synthesis of a-oligothiophenes, compounds of interest for the development of electronic devices such as organic field-effect transistors (OFETs), organic light-emitting diodes (OLEDs) and solar cells by iterative coupling sequence.[6] Following a one-pot protocol a series of pyrimidine p-systems with dador-aceptor-aceptor (D-A-A) and dador-aceptor-dador (D-A-D) configuration have been synthetized. These compounds show good photohemical properties such absorption in the UV or visible region, emitting visible light, large Stokes shifts and high fluorescence quantum yield for various applications in organic optoelectronic devices. [7] Further applications of our methodologies to other targets like molecular sensors are now underway.
[1] (a) Peña-López, M.; Martínez, M. M.; Sarandeses, L. A.; Pérez Sestelo, J. Chem. Eur. J. 2009, 15, 910-916. (b) Peña-López, M.; Martínez, M. M.; Sarandeses, L. A.; Pérez Sestelo, J. Org. Chem. 2010, 75, 5337-5339.
[2] (a) Peña-López, M.; Martínez, M. M.; Sarandeses, L. A.; Pérez Sestelo, J. Org. Lett. 2010, 12, 852-854. (b) Martínez, M. M.; Sarandeses, L. A.; Pérez Sestelo, J. Tetrahedron Lett. 2007, 48, 8536-8539. [3] (a) Mosquera, A.; Riveiros, R.; Pérez Sestelo, J.; Sarandeses, L. A. Org. Lett. 2008, 10, 3745-3748. (b) Pérez-Caaveiro, C.; Pérez Sestelo, J.; Martínez, M.; Sarandeses, L. A. J. Org. Chem. 2014, 79, 9586-9593. [4] Martínez, M. M.; Peña-López, M.; Pérez Sestelo, J.; Sarandeses, L. A. Org. Biomol. Chem. 2012, 10, 3892-3898. [5] Mosquera, Á.; Fernández, M. I.; Canle López, M.; Pérez Sestelo, J.; Sarandeses, L. Chem. Eur. J. 2014, 20, 15224. [6] Martínez, M. M.; Peña-López, M.; Pérez Sestelo, J.; Sarandeses, L. A. Org. Biomol. Chem. 2012, 10, 3892 [7] Pérez-Caaveiro, C.; Moreno Oliva, M.; López Navarrete, J. T. Pérez Sestelo, J.; Martínez, M. M.; Sarandeses, L. A. J. Org. Chem. 2019, in press. DOI: http://10.1021/acs.joc.9b00643