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Gil Valdo José da Silva

Associate Professor, FFCLRP-USP, since 1987

B. Sc. (1980)
Ph. D. (1984)
Postdoctoral fellow (Canada, 1984-1986, 1992-1993)

Research: Synthesis and Conformational Studies of Organic Compounds

Our research is aimed towards the synthesis of natural products and the development of synthetic methods. The target molecules are selected among natural products that show biological activity or that are isolated from medicinal plants. t-Crotonin and t-dehydrocrotonin, whose synthesis are under way in our laboratory, are substances isolated from Croton cajucara, a plant used in the folk medicine in the Amazon.

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We are also interested in conformational studies using computational methods and Nuclear Magnetic Resonance.

Selected Publications

bulletAdvances in the Synthesis of a-Methylenelactones.
Petragnani, N.; Ferraz, H. M. C.; Silva, G. V. J. Synthesis 1986, 157-183.
bulletTotal Synthesis of Both (+)-Compactin and (+)-Mevinolin. A General Strategy Based on the Use of a Special Titanium Reagent for Dicarbonyl Coupling.
Clive, D. L. J.; Keshava Murthy, K. S.; Wee, A. G. H.; Siva Prasad, J.; da Silva, G. V. J.; Majewski, M.; Anderson, P. C.; Evans, C. F.; Haugen, R. D.; Heeze, L. D.; Barrie, J. R. J. Am. Chem. Soc. 1990, 112, 3018-3028.
bulletSynthesis of 3-Substituted Furans.
da Silva, G. V. J.; Pelisson, M. M. M., Constantino, M. G. Tetrahedron Lett. 1994, 35, 7327-7330.
bulletPreparation of a Semisynthetic Analogue of Mevinolin and Compactin
Clive, D. L. J.; Wickens, P. L.; da Silva, G. V. J. J. Org. Chem. 1995, 60, 5532-5536.
bulletMoléculas em Três Dimensões: Um Estereoscópio para Computador
Constantino, M. G.; da Silva, G. V. J.; Pelisson, M. M. M. Química Nova 1998, 21, 337-340.
bulletStudies on the preparation of 3,4-disubstituted 2-methoxypyridines Pelisson, M. M. M.; da Silva, G. V. J.; Clive, D. L. J.; Coltart, D. M.; Hof, F. A. J. Heterocyclic Chem. 1999, 36, 653-658.
bulletDynamics of p-menthan-3,9-diols. A computational study in aqueous and chloroform solutions of two epimers. Namba, A.M.; Leon, S.; da Silva, G.V.J.; Aleman, C. Tetrahedron 2000, 56, 6089-6097.
bulletReduction and preparation of a phthalimide derivative from a furo-heliangolide. da Silva, G. V. J. ; Heleno, V. C. G.; Constantino, M. G. Molecules 2000, 5, 908-915
bulletPrincipal component analysis of long-range 'W' coupling constants of some cyclic compounds.
Constantino, M. G.; Lacerda Jr., V.; da Silva, G. V. J.; Tasic, L.; Rittner, R. J. Mol. Struct. 2001, 597, 129-136.
bulletTwo polycyclic compounds derived from a Diels-Alder reaction.
Zukerman-Schpector, J.; Caracelli, I.; Vega, M.; Constantino, M. G.; Beatriz, A.; da Silva, G. V. J. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 2001, 57, 646-648.
bulletSynthesis of benzofuranofuran derivatives: Model of natural products.
Donate, P. M.; da Silva, R.; da Silva, G. V. J.; Aleman, C. Synth. Commun. 2001, 31, 141-150.
bulletForce-field parametrization and molecular dynamics simulations of p-menthan-3,9-diols: a family of amphiphilic compounds derived from terpenoids.
Namba, A. M.; Leon, S.; da Silva, G. V. J.; Aleman, C. J. Comput.-Aided Mol. Des. 2001, 15, 235-245.
bulletCalculated and experimental NMR chemical shifts of p-menthane-3,9-diols. A combination of molecular dynamics and quantum mechanics to determine the structure and the solvent effects.
Casanovas, J.; Namba, A.M.; Leon, S.; Aquino, G.L.B.; da Silva, G.V.J.; Aleman, C. J. Org. Chem. 2001, 66, 3775-3782.
bulletChemical Equilibrium, Free Energy and Entropy of Mixing.
M. G. Constantino, G. V. J. da Silva, Chem. Educator 2002, 7, 349-353.
bulletNiobium Pentachloride Activation of Enone Derivatives: Diels-Alder and Conjugate Addition Products.
M. G. Constantino, V. Lacerda Júnior, G. V. J. da Silva, Molecules 2002, 7, 456-465.
bulletSynthetic Studies on Diels-Alder Adducts: Intramolecular Interactions Between Two Functions
M. G. Constantino, A. X. de Souza, G. V. J. da Silva, Molecules 2002, 7, 475-486.
bulletChemical Equilibrium, Free Energy and Entropy of Mixing.
M. G. Constantino, G. V. J. da Silva, Chem. Educator 2002, 7, 349-353.
bulletA Synthetic Approach to Bicyclo[6.2.1]undecane Ring Systems.
M. G. Constantino, K. T. de Oliveira, A. Beatriz, G. V. J. da Silva, Tetrahedron Lett. 2003, 44, 2641-2643.
bulletAn Efficient Synthesis of 3-Hydroxychromone Using Niobium Pentachloride.
M. G. Constantino, V. Lacerda Júnior, G. V. J. da Silva, J. Heterocyclic Chem. 2003, 40, 369-371.
bulletDetailed Assignments of 1H and 13C NMR Spectral Data of 14 Cyclopentane Derivatives.
M. G. Constantino, V. Lacerda Júnior, G. V. J. da Silva, Magn. Reson. Chem. 2003, 41, 641-643.
bulletAnalysis of the 1H and 13C NMR Spectra of Bicyclo[6.2.1]undecane Ring Systems.
M. G. Constantino, K. T. de Oliveira, A. Beatriz, G. V. J. da Silva,  Magn. Reson. Chem. 2003, 41, 726-728.
bulletNiobium (V) Chloride Mediated Preparation of b Chloro-a,b-Unsaturated Ketones.
M. G. Constantino, V. Lacerda Júnior, L. C. da Silva Filho, G. V. J. da Silva, Letters in Organic Chemistry, 2004, 1(4), 360-364.
bulletComplete assignment of 1H and 13C NMR data for three aryltetralin lignan lactones.
R. da Silva, V. C. G. Heleno, S. Albuquerque, J. K. Bastos, M. L. A. Silva, P. M. Donate, G. V. J. da Silva, Magnetic Resonance in Chemistry 2004, 42, 985-989.
bulletStructural Assignment of Diels-Alder Adducts: an Experimental and Theoretical Approach.
M. G. Constantino, L. C. da Silva Filho, A. Cunha Neto, V. C. G. Heleno, G. V. J. da Silva, J. L. C. Lopes, Spectrochimica Acta Part A 2005, 61(1-2), 171-176.
bulletDetailed Assignments of 1H and 13C NMR Spectral Data 0f 13 b-Substituted Cycloenones.
M. G. Constantino, V. Lacerda Júnior, G. V. J. da Silva, Magn. Reson. Chem. 2005, 43(4), 346-347.
bulletRacemic synthesis of 1,2-secomicrominutinin.
R. da Silva, P. M. Donate, G. V. J. da Silva, S. Pedersoli, C. Alemán, Journal of the Brazilian Chemical Society 2005, 16, 626-633.
bulletSynthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester.
V. Aragão, M. G. Constantino, A. Beatriz, G. V. J. da Silva, Molecules 2005, 10(11), 1413-1418.
bulletHigh Stereoselectivity on Low Temperature Diels-Alder Reactions.
L. C. da Silva Filho, V. Lacerda Júnior, M. G. Constantino, G. V. J. da Silva, P. R. Invernize, Beilstein Journal of Organic Chemistry 2005, 1, 14.
bulletDetailed 1H and 13C NMR structural assignment of three biologically active lignan lactones.
V. C. G. Heleno, R. da Silva, S. Pedersoli, S. Albuquerque, J. K. Bastos, M. L. A. Silva, P. M. Donate, G. V. J. da Silva, J. L. C. Lopes, Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 2006, 63, 234-239.
bulletAnalysis of a Cycloheptenone Derivative: an Experimental and Theoretical Approach.
K. T. Oliveira, V. Lacerda Júnior, M. G. Constantino, P. M. Donate, G. V. J. da Silva, T. J. Brocksom, D. Frederico, Spectrochimica Acta Part A 2006, 63(3), 709-713.
bulletLong-range JCH Heteronuclear Coupling Constants in Cyclopentane Derivatives.
V. Lacerda Júnior, G. V. J. da Silva, M. G. Constantino, C. F. Tormena, R. Thomas Williamson, B. L. Márquez, Magn. Reson. Chem. 2006, 44(1), 95-98.
bullet1H and 13C NMR Spectral Data for a Tricyclic Derivative of a Diels-Alder Adduct.
S. Pedersoli, M. G. Constantino, G. V. J. da Silva, Magn. Reson. Chem. 2006, 44(1), 83-86.
bulletCore Structure of Eremophilanes and Bakkanes through Niobium Catalyzed Diels-Alder Reaction: Synthesis of (±)-Bakkenolide A.
M. G. Constantino, K. T. Oliveira, E. C. Polo, G. V. J. da Silva, T. J. Brocksom, J. Org. Chem. 2006, 71, 9880-9883.
bulletSimulação de Desdobramentos Complexos de Espectros de RMN de 1H.
M. G. Constantino, G. V. J. da Silva, V. C. G. Heleno, I. A. Borin, I. P. de A. Campos, Química Nova 2006, 29(1), 160-167.
bulletNMR and Theoretical Investigation of the Keto-enol Tautomerism in Cyclohexane-1,3-diones.
V. Lacerda Júnior, M. G. Constantino, G. V. J. da Silva, Álvaro Cunha Neto, Cláudio F. Tormena, J. Mol. Struc. 2007, 828(1-3), 54-58.
bulletOpening of Epoxide Rings Catalyzed by Niobium Pentachloride.
M. G. Constantino, V. Lacerda Júnior, P. R. Invernize, L. C. da Silva Filho, G. V. J. da Silva, Synth. Commun. 2007, 37(20), 3529-3539.
bulletReatividade em Reações de Diels-Alder: Uma Prática Computacional.
V. Lacerda Júnior, Kleber Thiago de Oliveira, Rodrigo Costa e Silva, M. G. Constantino, G. V. J. da Silva, Química Nova 2007, 30(3), 727-730.
bulletAn approach to the synthesis of furanoheliangolides through Diels-Alder reactions.
M. G. Constantino, V. Aragão, G. V. J. da Silva, Tetrahedron Letters 2008, 49, 1393-1395.
bulletStereochemistry of cyclopentane derivatives from 2,3JCH dependence on dihedral angle (θ H-C-C-X).
V. Lacerda Junior, G. V. J. da Silva, M. G. Constantino, R. B. dos Santos, E. V. R. de Castro, R. C. Silva,  Magn. Reson. Chem. 2008, 46, 268-273.
bulletPurificação e caracterização de uma gentiohexaose obtida de botriosferana por hidrolise acida parcial.
N. K. Monteiro, P. F. Martinez, N. L. Izeli, A. F. D. Vasconcelos, M. S. Cardoso, M. L. C. Silva, A. M. Barbosa, R. F. H. Dekker, G. V. J. da Silva, L. A. B. de Moraes, Química Nova 2008, 31, 1015.
bullet Fast and Efficient Synthesis of Pyrano[3,2- c ]quinolines Catalyzed by Niobium(V) Chloride.
L. C. Silva-Filho, V. Lacerda Júnior, M. G. Constantino, G. V. J. da Silva, Synthesis 2008, 2527-2536.
bulletMonoamine oxidase inhibitory activities of indolyalkaloid toxins from the venom of the colonial spider Parawixia bistriata:  Functional characterization of PwTX-I.
D. M. Saidemberg, M. A. B. Ferreira, T. N. Takahashi, P. C. Gomes, L. M. M. Cesar-Tognoli, L. C. Silva-Filho, C. F. Tormena, G. V. J. da Silva, M. S. Palma, Toxicon 2009, 54, 717-724.
bulletDOSY NMR applied to analysis of flavonoid glycosides from Bidens sulphurea.
E. D. Rodrigues, D. B. Silva, D. C. R. Oliveira, G. V. J. da Silva, Magnetic Resonance in Chemistry 2009, 47, 1095-100.
bullet Configuration of stilbene derivatives by 1H NMR and theoretical calculation of chemical shifts.
R. Rotta, A. Cunha Neto, D. P. Lima, A. Beatriz, G. V. J. da Silva, Journal of Molecular Structure 2010, 975, 59-62.
bullet Cerium metal-mediated Reformatsky-type reaction with ethyl bromosuccinate for the synthesis of novel paraconic acid analogs.
S. M. M. Rodrigues, V. Nardini, M. G. Constantino, G. V. J. da Silva, Tetrahedron Letters 2012, 53, 6136-6137.
bullet Chemical constituents from three medicinal plants: Piper renitens, Siparuna guianensis and Alternanthera brasiliana.
V. A. Facundo, M. S. Azevedo, R. V. Rodrigues, L. F. Nascimento, J. S. L. T. Militão, G. V. J. da Silva, R. Braz-Filho, Revista Brasileira de Farmacognosia 2012, 22, 1134-1139.
bullet Side-chain Modifications of Highly Functionalized 3(2H)-Furanones.
V. Nardini, S. M. M. Rodrigues, M. G. Constantino, G. V. J. da Silva, Molecules 2012, 17, 12151-12162.
bullet Studies towards rotational dynamics of dimethyl 2-(triphenylphosphoranylidene) succinate by 1H NMR.
S. M. M. Rodrigues, V. Palaretti, V. Nardini, M. G. Constantino, G. V. J. da Silva, Journal of Molecular Structure THEOCHEM 2013, 1051, 276-279.
bullet Assignment of NMR data and relative stereochemistry determination of paraconic acid derivatives.
S. M. M. Rodrigues, V. Nardini, R. F. Moral, M. G. Constantino, G. V. J. da Silva, Journal of Molecular Structure 2013, 1053, 100-105.
bullet Synthesis of the bicyclo[6.2.1]undecane ring system by a solvent-free Diels–Alder reaction.
A. Beatriz, R. S. Gomes, M. G. Constantino, G. V. J. da Silva, K. T. Oliveira, Tetrahedron Letters 2014, 55, 679-681.
bullet Post-column sodiation to enhance the detection of polyacetylene glycosides in LC–DAD–MS analyses: An example from Bidens gardneri (Asteraceae).
D. B. Silva, E. D. Rodrigues, G. V. J. da Silva, N. P. Lopes, D. C. R. Oliveira, Talanta 2015, 135, 87-93.
bulletOne-step Synthesis of Indanones Through NbCl5-induced  Friedel-Crafts Reaction.
J. S. Barbosa, G. V. J. da Silva, M. G. Constantino, Tetrahedron Letters 2015, 56, 4649-4652.

This page was last updated on 07/07/15