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Prof. Dr. ANTONIO CARLOS BENDER BURTOLOSO

Foto Docente

Histórico

Possui graduação em Química com atribuição tecnológica pela Universidade Federal do Rio de Janeiro (2001), mestrado em Química de Produtos Naturais pela Universidade Federal do Rio de Janeiro (2002) e doutorado em Química pela Universidade Estadual de Campinas (2006). Em 2007, finalizou seu pós-doutoramento no TSRI (The Scripps Research Institute) sob a orientação do professor KC Nicolaou (síntese do fragmento LMNO da maitotoxina). Em 2008, ingressou como Professor doutor no Instituto de Química de São Carlos da Universidade de São Paulo (IQSC - USP). Foi jovem pesquisador apoiado pela FAPESP (2008-2012) e foi eleito em 2012 Membro Afiliado da Academia Brasileira de Ciências para o período 2012-2017. Desde 2015, é livre-docente e professor Associado pelo IQSC-USP.


Linhas de Pesquisa

1) New Methodologies from Sulfur Ylides and Diazo Compounds
2) Biomass Chemistry: Synthesis of Valuable Chemicals, Lignin Models and Chemical Degradation of Lignin
3) Total Synthesis:
4) Green and Environmental Chemistry


Publicações

36. BERNARDIM, BARBARA; CAL, PEDRO M.S.D.; MATOS, MARIA J.; OLIVEIRA, BRUNO L.; MARTÍNEZ-SÁEZ, NURIA; ALBUQUERQUE, INÊS S.; PERKINS, ELIZABETH; CORZANA, FRANCISCO; Burtoloso, Antonio C.B.; JIMÉNEZ-OSÉS, GONZALO; BERNARDES, GONÇALO J. L.
Stoichiometric and irreversible cysteine-selective protein modification using carbonylacrylic reagents. Nature Communications. , v.7, p.13128 - , 2016.

35. DIAS, RAFAEL M. P.; Burtoloso, Antonio C. B.
Catalyst-Free Insertion of Sulfoxonium Ylides into Aryl Thiols. A Direct Preparation of β-Keto Thioethers. Organic Letters (Print). , v.18, p.3034 - 3037, 2016.

34. KAWAMURA, MEIRE YASUKO; TALERO, ALEXÁNDER GARAY; SANTIAGO, JOÃO VICTOR; GARAMBEL-VILCA, EDSON; ROSSET, ISAC G.; Burtoloso, Antonio Carlos Bender
Six-Step Syntheses of (-)-1-deoxyaltronojirimycin and (+)-1-deoxymannonojirimycin from N-Z-O-TBDPS-L-serinal. Journal of Organic Chemistry. , 81, p.10569-10575

33. MATTSON, ANITA; BURTOLOSO, ANTONIO; BERNARDIM, BARBARA; COUCH, ERICA; HARDMAN-BALDWIN, ANDREA
Divergent Roles of Urea and Phosphoric Acid Derived Catalysts in Reactions of Diazo Compounds. Synthesis (Stuttgart). , v.48, p.677 - 686, 2016.

32. BURTOLOSO, ANTONIO; SANTIAGO, JOÃO; BERNARDIM, BARBARA; TALERO, ALEXÁNDER
Advances in the Enantioselective Metal-catalyzed N-H and O-H Insertion Reactions with Diazocarbonyl Compounds. Current Organic Synthesis. , v.12, p.650 - 659, 2015.

31. METZKER, GUSTAVO; Burtoloso, Antonio C. B.
Conversion of levulinic acid into gamma-valerolactone using Fe (CO) : mimicking a biorefinery setting by exploiting crude liquors from biomass acid hydrolysis. Chemical Communications (London. 1996. Print). , v.51, p.14199-14202, 2015.

30. Burtoloso, Antonio C. B., DIAS, RAFAEL M. P., BERNARDIM, BARBARA a,b-Unsaturated Diazoketones as Useful Platforms in the Synthesis of Nitrogen Heterocycles. Accounts of Chemical Research. , v.48, p.150319143140008 , 2015.

29. BERNARDIM, BARBARA, HARDMAN-BALDWIN, ANDREA M., Burtoloso, Antonio C. B. LED lighting as a simple, inexpensive, and sustainable alternative for Wolff rearrangements. RSC Advances: an international journal to further the chemical sciences , v.5, p.13311 – 13314, 2015.

28. PAPA, T. B. R., PINHO, V. D., NASCIMENTO, E. S. P. DO, SANTOS, W. G., BURTOLOSO, A. C. B., SKIBSTED, L. H., CARDOSO, D. R. Astaxanthin diferulate as a bifunctional antioxidant. Free Radical Research , v.49, p.102 – 111, 2015.

27. ROSSET, I. G., DIAS, R. M. P., PINHO, V. D., BURTOLOSO, A. C. B. Three-Step Synthesis of (±)-Preussin from Decanal. Journal of Organic Chemistry, v.79, p.6748 – 6753, 2014.

26. BERNARDIM, BARBARA, BURTOLOSO, A. C.B. A two-step synthesis of the bioprotective agent JP4-039 from N-Boc-l-leucinal. Tetrahedron (Oxford. Print), v.70, p.3291 – 3296, 2014.

25. ROSSET, I. G.; BURTOLOSO, A. C. B. Preparation of Z-alpha,beta-Unsaturated Diazoketones from Aldehydes. Application in the Construction of Substituted Dihydropyridin-3-ones. Journal of Organic Chemistry, v.78, p.9464 – 9470, 2013.

24. BURTOLOSO, A. C. B.; DIAS, R. M. P.; LEONARCZYK, I. A. Sulfoxonium and Sulfonium Ylides as Diazocarbonyl Equivalents in Metal-Catalyzed Insertion Reactions. European Journal of Organic Chemistry (Print), v.23, p. 5005-5016, 2013.

23. PINHO, V. D.; PROCTER, DAVID J. ; Burtoloso, Antonio C. B. . SmI -Mediated Couplings of α-Amino Acid Derivatives. Formal Synthesis of (−)-Pumiliotoxin 251D and ( )-Epiquinamide. Organic Letters (Print), v.15, p. 2434-2437 , 2013.

22. SGOBBI, L. F., RAZZINO, C. A., ROSSET, I. G., BURTOLOSO, A. C.B., MACHADO, S. A.S. Electrochemistry and UV-vis spectroscopy of synthetic thiocholine: Revisiting the electro-oxidation mechanism. Electrochimica Acta, v.112, p.500 – 504, 2013.

21. BURTOLOSO, A. C. B., BERTONHA, A. F., ROSSET, I. G. Synthesis of Alkaloids: Recent Advances in the Synthesis of Phenanthroindolizidine Alkaloids. Current Topics in Medicinal Chemistry (Print), v.14, p.191 – 199, 2013.

20. BERNARDIM, B.; LORDELLO, L.; BURTOLOSO, A. C. B. α,β-Unsaturated Diazoketones as Versatile Building Blocks for the Synthesis of Hydroxylated Piperidines, Indolizidines and Quinolizidines. Current Topics in Medicinal Chemistry (Print), v.13, p.2099 – 2103, 2013.

19. SGOBBI, LIVIA F. ; PINHO, V. D.; CABRAL, MURILO F. ; Burtoloso, Antonio C.B. ; MACHADO, SERGIO A.S. . Hydrazone molecules as mimics for acetylcholinesterase. A new route towards disposable biosensors for pesticides?. Sensors and Actuators. B, Chemical, v. 182, p. 211-216, 2013.

18. BERNARDIM, B. ; PINHO, V. D. ; BURTOLOSO, A. C. B. . α,β-Unsaturated Diazoketones as Platforms in the Asymmetric Synthesis of Hydroxylated Alkaloids. Total Synthesis of 1-Deoxy-8,8a-diepicastanospermine and 1,6-Dideoxyepicastanospermine and Formal Synthesis of Pumiliotoxin 251D. Journal of Organic Chemistry, v. 77, p. 9926-9931, 2012.

17. Pinho, V. D.; Burtoloso, A. C. B. Total Synthesis of (-)-Indolizidine 167B via an Unusual Wolff Rearrangement from an α,β-Unsaturated Diazoketone. Tetrahedron Letters, v. 53, p. 876-878, 2012.

16. PINHO, V. D. ; BURTOLOSO, A. C. B. . Correction to Preparation of α,β-Unsaturated Diazoketones Employing a Horner Wadsworth Emmons Reagent. Journal of Organic Chemistry, v. 76, p. 6979-6979, 2011.

15. Pinho, V. D.; BURTOLOSO, A. C. B. Preparation of a,b-Unsaturated Diazoketones Employing a Horner-Wadsworth-Emmons Reagent. Journal of Organic Chemistry, v. 76, p. 289-292, 2011.

14. Berlinck, Roberto G. S. ; BURTOLOSO, A. C. B. ; Trindade-Silva, Amaro E. ; Romminger, Stelamar ; Morais, Raquel P. ; Bandeira, Karin ; Mizuno, Carolina M. . The chemistry and biology of organic guanidine derivatives. Natural Product Reports (Print), v. 27, p. 1871-1907, 2010.

13. Carita, Adriana ; BURTOLOSO, A. C. B. . An epoxide ring-opening approach for a short and stereoselective synthesis of icetexane diterpenoids. Tetrahedron Letters, v. 51, p. 686-688, 2010.

12. PRADO, V. S. ; BURTOLOSO, A. C. B. . An Improved Procedure for the Preparation of [Bis(2,2,2-trifluoroethyl)phosphono]acetic Acid. Synthesis (Stuttgart), v. 2010, p. 361-363, 2010.

11. BURTOLOSO, A. C. B. . Catalytic Enantioselective alpha-Arylation of Carbonyl Compounds. Synlett, p. 320-327, 2009.

10. Berlinck, RGS ; BURTOLOSO, A. C. B. ; Kossuga, M. H. . The chemistry and biology of organic guanidine derivatives. Natural Product Reports, v. 25, p. 919, 2008.

9. BURTOLOSO, A. C. B. ; CORREIA, C. R. D. . Stereoselective synthesis of azetidine-derived glutamate and aspartate analogues from chiral azetidin-3-ones. Tetrahedron, v. 64, p. 9928-9936, 2008.

8. NICOLAOU, K. C. ; FREDERICK, M. ; BURTOLOSO, A. C. B. ; DENTON, R. ; RIVAS, F. ; COLE, K. ; AVERSA, R. ; GIBE, R. ; UMEZAWA, T ; SUZUKI, T.; Chemical Synthesis of the GHIJKLMNO Ring System of Maitotoxin. Journal of the American Chemical Society, v. 130, p. 7466-7476, 2008.

7. BURTOLOSO, A. C. B. ; CORREIA, C. R. D.; A new entry to the synthesis of substituted azetidines: [2+2] cycloaddition reaction of four-membered endocyclic enamides to ketenes. Tetrahedron Letters, v. 47, p. 6377-6380, 2006.

6. BURTOLOSO, A. C. B. ; GARCIA, A. L. L. ; MIRANDA, K. C. ; CORREIA, C. R. D.; Heck arylation of maleic anhydrides using arenediazonium tetrafluoroborates: synthesis of mono- and diarylated maleic anhydrides and of the marine alkaloids prepolycitrin A and polycitrin A. Synlett (Stuttgart), v. x, p. 3145-3149, 2006.

5. BURTOLOSO, A. C. B. ; ALBUQUERQUE, M. G. ; AGUIAR, L. C. S.; Theoretical Studies of the Asymmetric Alkylation Reaction on Chiral Enamines. Journal of Molecular Structure. Theochem, v. 716, p. 103-107, 2005.

4. BURTOLOSO, A. C. B. ; CORREIA, C. R. D.; Stereoselective Synthesis of the Conformationally Constrained Glutamate Analogue, (-)-(2R,3S)-cis-2-carboxyazetidine-3-acetic acid, from (S)-N-tosyl-2-phenylglycine. Synlett, n. 10, p. 1559-1562, 2005.

3. BURTOLOSO, A. C. B. ; CORREIA, C. R. D.; Asymmetric Synthesis of cis-2,4-Disubstituted Azetidin-3-ones from Metal Carbene Chemistry. Journal of Organometallic Chemistry, v. 690, p. 5636-5646, 2005.

2. BURTOLOSO, A. C. B.; Copper (II) Acetylacetonate: An Inexpensive Multifunctional Catalyst. Synlett (Stuttgart), v. x, n. 18, p. 2859-2860, 2005.

1. BURTOLOSO, A. C. B. ; CORREIA, C. R. D.; Metal Carbene N-H Insertion of Chiral a,a-Dialkyl-a-Diazoketones. A Novel and Consice Method for the Stereocontrolled Synthesis of Fully-Substituted Azetidines. Tetrahedron Letters, v. 45, p. 3355-3358, 2004.


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