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.
We are also interested in conformational studies using computational methods and
Nuclear Magnetic Resonance.
Selected Publications
 | Advances in the Synthesis of a-Methylenelactones.
Petragnani, N.; Ferraz, H. M. C.; Silva, G. V. J. Synthesis 1986, 157-183.
|
| Total 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. |
| Synthesis of 3-Substituted Furans.
da Silva, G. V. J.; Pelisson, M. M. M., Constantino, M. G. Tetrahedron Lett. 1994,
35, 7327-7330. |
| Preparation 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. |
| Moléculas 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. |
| Studies 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. |
| Dynamics 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. |
| Reduction 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 |
| Principal 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. |
| Two 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. |
| Synthesis 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. |
| Force-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. |
| Calculated 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. |
| Chemical Equilibrium, Free Energy and
Entropy of Mixing.
M. G. Constantino, G. V. J. da Silva, Chem. Educator 2002, 7,
349-353. |
| Niobium 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. |
| Synthetic 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. |
| Chemical Equilibrium, Free Energy and
Entropy of Mixing.
M. G. Constantino, G. V. J. da Silva, Chem. Educator 2002, 7,
349-353.
|
| A 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. |
| An 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. |
| Detailed 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. |
| Analysis 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. |
| Niobium (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. |
| Complete 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. |
| Structural 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. |
| Detailed 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. |
| Racemic 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. |
| Synthesis 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. |
| High 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. |
| Detailed 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. |
| Analysis 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. |
| Long-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. |
| 1H 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. |
| Core 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. |
| Simulação 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. |
| NMR 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. |
| Opening 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. |
| Reatividade
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. |
| An
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. |
| Stereochemistry 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. |
| Purificação 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. |
|
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. |
| Monoamine 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. |
| DOSY 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. |
|
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. |
|
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. |
|
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. |
|
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. |
|
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. |
|
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. |
|
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. |
|
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. |
| One-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 |
