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Mauricio Gomes Constantino

Full Professor, FFCLRP-USP, since 2006
Member of the University staff since 1975
(Regional Editor of Molecules)

B. Sc. ("Licenciatura") (1970)
M. Sc. (1974)
Ph. D. (1977)
Postdoctoral fellow (USA, 1979-1980)
"Livre-Docente" (1982)
Postdoctoral fellow (Germany and England, 1985)

 

Research: Synthesis of Natural Products

Our main interest is the synthesis of biologically active natural products. Abscisic acid (a vegetal hormone) and Artemisinin (a strong anti-malaria agent) are illustrative examples of substances already synthesized in our laboratory.

Fig1MauEMaior.gif (5001 bytes)

We are presently developing methods for the synthesis of goyazensolide, of products extracted from Otoba parvifolia, of microbiotol, etc. See under Current Research for more details.

We do also some investigations on novel organic reactions, analytical methods and development of software and equipment for research and educational purposes. See under Software some of the programs we have developed as part of our research work.

Selected Publications

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Synthesis
bulletM. G. Constantino, P. M. Donate and N. Petragnani, "An Efficient Synthesis of (±)-Abscisic Acid", J. Org. Chem. 51, 253 (1986).
bulletM. G. Constantino, P. M. Donate and N. Petragnani, "Hydration of Diacetylene Compounds. Synthesis of a Marine Natural Product: (±)-1-(2,6,6-Trimethyl-4-hydroxycyclohexenyl)--1,3-butanedione", J. Org. Chem. 51, 387-390 (1986).
bulletM. G. Constantino, P. Losco and E. E. Castellano, "A Novel Synthesis of (±)-Abscisic Acid", J. Org. Chem. 54, 681-683 (1989).
bulletM. G. Constantino, M. Beltrame Jr., G. V. J. da Silva and J. Zukerman-Schpector, "A Novel Asymmetric Synthesis of (+)-Artemisinin", Synth. Commun. 26, 321-329 (1996).
bulletM. G. Constantino, L. G. O. Matias, G. V. J. da Silva, V. C. G. Heleno and M. T. P. Gambardella, "Stereoselective Synthesis of b -Hydroxy- and b -Ethoxy-d -lactones: Model Structures for Compounds Isolated from Otoba parvifolia", Synth. Commun. 27, 4285-4295 (1997).
bulletM. G. Constantino, A. Beatriz and G. V. J. da Silva, "A Model Synthesis of the Bicyclic Core Structure of the Furanoheliangolide Sesquiterpenes", Tetrahedron Lett. 41, 7001-7004 (2000).
bulletM. G. Constantino, K. T. de Oliveira, A. Beatriz and G. V. J. da Silva, "A Synthetic Approach to Bicyclo[6.2.1]undecane Ring Systems", Tetrahedron Lett. 44, 2641-2643 (2003).
bulletM. G. Constantino, V. Lacerda Jr. and G. V. J. da Silva, "An Efficient Synthesis of 3-Hydroxychromone Using Niobium Pentachloride", J. Heterocyclic Chem. 40, 369-371 (2003).
bulletP. M. Donate, D. Frederico, R. da Silva, M. G. Constantino, G. Del Ponte and P. S. Bonato,  "Asymmetric Synthesis of g-Butyrolactones by Enantioselective Hydrogenation of Butenolides", Tetrahedron:Asymmetry 14, 3253-3256 (2003).
bulletD. Frederico, P. M. Donate, M. G. Constantino, E. S. Bronze and M. I. Sairre, "A Short and Efficient Synthesis of Crocetin-dimethylester and Crocetindial", J. Org. Chem. 68, 9126-9128 (2003).
bulletV. Aragão, M. G. Constantino, A. Beatriz and G. V. J. da Silva, “Synthesis of 1-Methyl-3-oxo-7-oxabicyclo[2.2.1]hept-5-ene-2-carboxylic Acid Methyl Ester”, Molecules 10, 1413-1418 (2005).
bulletM. G. Constantino, K. T. Oliveira, E. C. Polo, G. V. J. da Silva and T. J. Brocksom, “Core Structure of Eremophilanes and Bakkanes through Niobium Catalyzed Diels-Alder Reaction: Synthesis of (±)-Bakkenolide A”, J. Org. Chem. 71, 9880-9883 (2006).
bulletM. G. Constantino, V. Aragão and G. V. J. da Silva, “An Approach to the Synthesis of Furanoheliangolides Through Diels-Alder Reactions”, Tetrahedron Letters 2008, 49, 1393-1395. DOI: 10.1016/j.tetlet.2007.12.079
bullet D. C. Sass, V. C. G. Heleno, J. L. C. Lopes and M. G. Constantino, One-step Biomimetic Conversion of a Furanoheliangolide into an Eremantholide Using Stryker's Reagent”, Tetrahedron Letters 2008, 49, 3877-3880.
bullet D. C. Sass, K. T. Oliveira and M. G. Constantino, Synthesis of Homoallylic Oxygenated alfa-methylene-gamma-butyrolactones: a Model for Preparing Biologically Active Natural Lactones”, Tetrahedron Letters 2008, 49, 5770-5772.
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L. C. da Silva Filho, V. L. Júnior, M. G. Constantino and G. V. J. da Silva, Fast and Efficient Synthesis of Pyrano[3,2- c ]quinolines Catalyzed by Niobium(V) Chloride”,  Synthesis”, Journal of Synthetic Organic Chemistry 2008, 2527-2536.

bulletD. Frederico, M. G. Constantino and P. M. Donate, Total Synthesis of (3S, 5R, 3'S, 5'R)-Capsorubin, Journal of the Brazilian Chemical Society 2009, 20, 888-894.
bulletA. F. Nascimento, M. G. Constantino and P. M. Donate, Total Synthesis of Aripuanin, a Megastigmane from Ficus aripuanensis, Orbital: The Electronic Journal of Chemistry 2012, 4, 253-262.
bulletD. C. Sass, V. C. G. Heleno, J. S. Barbosa, G. O. Morais, F. B. Costa and M. G. Constantino, “Biomimetic Synthesis of Diversifolin”, Tetrahedron Letters 2013, 54, 625-627.
bullet A. Beatriz, R. S. Gomes, M. G. Constantino, G. V. J. da Silva and K. T. Oliveira, Synthesis of the Bicyclo[6.2.1]undecane Ring System by a Solvent-free Diels–Alder Reaction”, Tetrahedron Letters 55, 679-681 (2014).

 

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Organic Reactions
bulletM. G. Constantino, I. Carvalho, G. V. J. da Silva and F. C. Archanjo, "Hydration of Acetylenic Esters: Synthesis of b -Keto-Esters", Molecules 1, 72-78 (1996). Reprint.
bulletM. G. Constantino, L. G. O. Matias, G. V. J. da Silva, V. C. G. Heleno and M. T. P. Gambardella, "Stereoselective Synthesis of b -Hydroxy- and b -Ethoxy-d -lactones: Model Structures for Compounds Isolated from Otoba parvifolia", Synth. Commun. 27, 4285-4295 (1997).
bulletM. G. Constantino, L. G. O. Matias, G. V. J. da Silva, E. Barbieri and M. T. P. Gambardella, "Stereoselective Sodium Borohydride Reductions of Cyclopentanones: Influence of Ceric Chloride on the Stereochemistry of Reaction", Química Nova 21, 719-721 (1998).
bulletP. M. Donate, M. G. Constantino, R. da Silva and S. Pedersoli, "Synthesis of Substituted g-Butyrolactones: b-Hydroxymethyl-, b-Methylene and Cyclopropane Derivatives", Synth. Commun.29, 2923-2936 (1999).
bulletM. G. Constantino, P. M. Donate, D. Frederico, T. V. Carvalho, L. E. Cardoso and J. Zukerman-Schpector, "Ring Contraction Through Epoxide Rearrangement: A Formal Synthesis of Capsorubin", Synth. Commun. 30, 3327-3340 (2000).
bulletG. V. J. da Silva, V. C. G. Heleno and M. G. Constantino, "Reduction and Preparation of a Phthalimide Derivative from a Furo-heliangolide", Molecules 5, 908-915 (2000). Reprint.
bulletM. G. Constantino, A. Beatriz, G. V. J. da Silva and J. Zukerman-Schpector, "Synthetic Studies on the Diels-Alder Adduct from 3,4-Dimethoxyfuran and Benzoquinone", Synth. Commun. 31, 3329-3336 (2001).
bulletM. G. Constantino, V. Lacerda Jr. and V. Aragão, "Niobium Pentachloride Catalysed Ring Opening of Epoxides", Molecules 6, 770-776 (2001). Reprint.
bulletM. G. Constantino, V. Lacerda Jr. and G. V. J. da Silva, "Niobium Pentachloride Activation of Enone Derivatives: Diels-Alder and Conjugate Addition Products", Molecules 7, 456-465 (2002).
bulletM. G. Constantino, A. X. de Souza and G. V. J. da Silva, "Synthetic Studies on Diels-Alder Adducts: Intramolecular Interactions Between Two Functions", Molecules 7, 475-486 (2002).
bulletM. G. Constantino, V. L. Júnior, L. C. da Silva Filho and G. V. J. da Silva, “Niobium (V) Chloride Mediated Preparation of b Chloro-a,b-Unsaturated Ketones”, Letters in Organic Chemistry, 1, 360-364 (2004).
bulletL. C. da Silva Filho, V. L. Júnior, M. G. Constantino, G. V. J. da Silva and P. R. Invernize, “High Stereoselectivity on Low Temperature Diels-Alder Reactions”, Beilstein Journal of Organic Chemistry 1, 14 (2005).
bulletM. G. Constantino, V. L. Júnior, P. R. Invernize, L. C. da Silva Filho and G. V. J. da Silva, “Opening of Epoxide Rings Catalyzed by Niobium Pentachloride”, Synth. Commun. 37, 3529-3539 (2007).
bullet D. C. Sass, V. C. G. Heleno, G. O. Morais, J. L. C. Lopes, N. P. Lopes and M. G. Constantino, Selectivity in Reduction of Natural Furanoheliangolides with Stryker's Reagent”, Organic & Biomolecular Chemistry 2011, 9, 6148.
bullet D. C. Sass, E. C. De Lucca, J. S. Barbosa, K. T. Oliveira and M. G. Constantino, Tandem Reduction + Cyclization of ortho-Substituted Cinnamic Esters”, Tetrahedron Letters 2011, 52, 5371-5374.
bullet S. M. M. Rodrigues, V. Nardini, M. G. Constantino and G. V. J. da Silva, Cerium Metal-mediated Reformatsky-type Reaction with Ethyl Bromosuccinate for the Synthesis of Novel Paraconic Acid Analogs”, Tetrahedron Letters 2012, 53, 6136-6137.
bullet D. C. Sass, V. C. G. Heleno, S. Cavalcante, J. N. Silva, A. C. F. Soares and M. G. Constantino, Solvent Effect in Reactions Using Stryker s Reagent, Journal of Organic Chemistry 2012, 77, 9374-9378.
bullet V. Nardini, S. M. M. Rodrigues, M. G. Constantino and G. V. J. da Silva, Side-chain Modifications of Highly Functionalized 3(2H)-Furanones”, Molecules 2012, 17, 12151-12162.

 

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NMR and Theoretical Studies
bulletM. G. Constantino and G. V. J. da Silva, "Stereochemistry in Substituted Cyclopentanes: An Approach to the Analysis by Proton NMR", Tetrahedron 54, 11363-11364 (1998).
bulletM. G. Constantino, V. Lacerda Jr., G. V. J. da Silva, L. Tasic and R. Rittner, "Principal Component Analysis of Long Range "W" Coupling Constants of Some Cyclic Compounds", J. Mol. Struc., 597/1-3, 129-136 (2001).
bulletM. G. Constantino, A. X. de Souza and G. V. J. da Silva, "Synthetic Studies on Diels-Alder Adducts: Intramolecular Interactions Between Two Functions", Molecules 7, 475-486 (2002).
bulletM. G. Constantino and G. V. J. da Silva, "Chemical Equilibrium, Free Energy and Entropy of Mixing", Chem. Educator 7, 349-353 (2002).
bulletM. G. Constantino, V. Lacerda Jr. and G. V. J. da Silva, "Detailed Assignments of 1H and 13C NMR Spectral Data of 14 Cyclopentane Derivatives", Magn. Reson. Chem. 41, 641-643 (2003).
bulletM. G. Constantino, K. T. de Oliveira, A. Beatriz and G. V. J. da Silva, "Analysis of the 1H and 13C NMR Spectra of Bicyclo[6.2.1]undecane Ring Systems", Magn. Reson. Chem. 41, 726-728 (2003).
bulletV. C. G. Heleno, A. E. M. Crotti, M. G. Constantino, N. P. Lopes and J. L. C. Lopes, "Total Assignment of 1H and 13C NMR Data for the Sesquiterpene Lactone 15-Deoxygoyazensolide", Magn. Reson. Chem. 42, 364-367 (2004).
bulletM. G. Constantino, L. C. da Silva Filho, A. Cunha Neto, V. C. G. Heleno, G. V. J. da Silva and J. L. C. Lopes, “Structural Assignment of Diels-Alder Adducts: an Experimental and Theoretical Approach”, Spectrochimica Acta Part A 61, 171-176 (2005).
bulletM. G. Constantino, V. L. Júnior and G. V. J. da Silva, “Detailed Assignments of 1H and 13C NMR Spectral Data 0f 13 b-Substituted Cycloenones”, Magn. Reson. Chem. 43, 346-347 (2005).
bulletK. T. Oliveira, V. L. Júnior, M. G. Constantino, P. M. Donate, G. V. J. da Silva, T. J. Brocksom and D. Frederico, “Analysis of a Cycloheptenone Derivative: an Experimental and Theoretical Approach”, Spectrochimica Acta Part A 63, 709-713 (2006).
bulletV. L. Júnior, G. V. J. da Silva, M. G. Constantino, C. F. Tormena, R. Thomas Williamson and B. L. Márquez, “Long-range JCH Heteronuclear Coupling Constants in Cyclopentane Derivatives”, Magn. Reson. Chem. 44, 95-98 (2006).
bulletS. Pedersoli, M. G. Constantino and G. V. J. da Silva, “1H and 13C NMR Spectral Data for a Tricyclic Derivative of a Diels-Alder Adduct”, Magn. Reson. Chem. 44, 83-86 (2006).
bulletM. G. Constantino, G. V. J. da Silva, V. C. G. Heleno, I. A. Borin and I. P. de A. Campos, “Simulação de Desdobramentos Complexos de Espectros de RMN de 1H”, Química Nova 29, 160-167 (2006).
bulletG. F. Caramori, K. T. Oliveira, S. E. Galembeck, P. Bultinck and M. G. Constantino, “Aromaticity and Homoaromaticity in Methano[10]annulenes”, J. Org. Chem. 72, 76-85 (2007).
bulletV. L. Júnior, M. G. Constantino, G. V. J. da Silva, Á. Cunha Neto and C. F. Tormena, “NMR and Theoretical Investigation of the Keto-enol Tautomerism in Cyclohexane-1,3-diones”, J. Mol. Struc. 828, 54-58 (2007).
bulletV. L. Júnior, G. V. J. da Silva, M. G. Constantino, R. B. dos Santos, E. V. R. de Castro and R. C. Silva, “Stereochemistry of Cyclopentane Derivatives from 2,3JCH Dependence on Dihedral Angle (θ H-C-C-X)”, Magn. Reson. Chem. 46, 268-273 (2008).
bullet D. C. Sass, V. C. G. Heleno, A. C. F. Soares, J. L. C. Lopes and M. G. Constantino,  Detailed 1H and 13C NMR structural assignment and relative stereochemistry determination for three new and one known semi-synthetic sesquiterpene lactones, Journal of Molecular Structure 2012, 1008, 24-28.
bullet S. M. M. Rodrigues, V. Nardini, R. F. Moral, M. G. Constantino and G. V. J. da Silva, Assignment of NMR Data and Relative Stereochemistry Determination of Paraconic Acid Derivatives”, Journal of Molecular Structure 2013, 1053, 100-105.
bullet S. M. M. Rodrigues, V. Palaretti, V. Nardini, M. G. Constantino and G. V. J. da Silva, Studies Towards Rotational Dynamics of Dimethyl 2-(triphenylphosphoranylidene) Succinate by 1H NMR”, Journal of Molecular Structure THEOCHEM 2013, 1051, 276-279

 

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Education, Equipment, etc.
bulletM. G. Constantino, "Utilização de Micro-Computadores em Aulas de Ressonância Magnética Nuclear de Próton", Química Nova 11, 299 (1988).
bulletM. G. Constantino and G. V. J. Silva, "Um Desumidificador de Ar para Aparelhos de RMN", Química Nova 12, 174 (1989).
bulletI. Carvalho, M. G. Constantino and G. V. J. Silva, "Simples e Eficiente Método para Dosar LDA", Química Nova 12, 177 (1989).
bulletM. G. Constantino and E. R. Oliveira, "Um Seguro Controle de Aquecimento para Laboratório", Química Nova 14, 120 (1991).
bulletM. G. Constantino, G. V. J. da Silva and M. M. M. Pelisson, "Moléculas em Três Dimensões: Um Estereoscópio Para Computador", Química Nova 21, 337-340 (1998).
bulletM. G. Constantino and A. X. de Souza, "Modelos Para o Carbono sp3: Quatro Pirâmides no Tetraedro", Química Nova 21, 662-665 (1998).
bulletM. G. Constantino and G. V. J. da Silva, "A Transformada de Fourier em Basic", Química Nova 23, 413-417 (2000).
bulletV. J. Júnior, Kleber Thiago de Oliveira, Rodrigo Costa, M. G. Constantino and G. V. J. da Silva, “Reatividade em Reações de Diels-Alder: Uma Prática Computacional”, Química Nova 30, 727-730 (2007).

This page was last updated on 06/23/15