Antonio Carlos Bender Burtoloso
CV Lattes
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Universidade de São Paulo (USP). Instituto de Química de São Carlos (IQSC) (Institutional affiliation for the last research proposal) Birthplace: Brazil
bachelor's at Química com atribuição tecnológica from Universidade Federal do Rio de Janeiro (2001), master's at Chemistry from Universidade Federal do Rio de Janeiro (2002) and doctorate at Chemistry from Universidade Estadual de Campinas (2006). Has experience in Chemistry, focusing on Organic Synthesis, acting on the following subjects: grupamento acila, glicidóis and ditiana. (Source: Lattes Curriculum)
- Synthesis of substituted cyclopentanes and long chain polyols from abundant chemical platforms derived from biomass, AP.R
Abstract
The expansion of products that can be obtained through the transformation of vegetal biomass has been a great challenge, especially in the case of complex molecules with high added value. In this case, it is important to develop new methodologies or synthetic transformations that can supply new compounds from raw materials that are easily obtained from the biomass in abundant form (levu...
- Molecular design, synthesis and trypanocidal activity of cruzain reversible covalent inhibitors, AP.TEM
Abstract
Cruzain, the main cysteine protease of Trypanosoma cruzi, is an essential enzyme for the life cycle of the parasite and has been used as a viable target for searching for enzyme inhibitors as drug candidates. The peptide mimetic compound K11777 inhibits cruzain at nanomolar concentrations, and acts by an irreversible inhibition mechanism. Analogs or derivatives K11777 usually contain el...
- Development of new methodologies for the asymmetric a-functionalization of carbonyl compounds using chiral catalysts, AP.R
Abstract
Subproject A: Synthesis of prochiral b-cetosulfoxonium ylides and its application in asymmetric insertion reactions catalyzed by gold. Subproject B: The use of Bronsted acids in the organocatalytic decomposition of diazo compounds in the presence of nucleophilic agents. (AU)
- Organocatalytic insertion reactions for drug discovery, AP.R
Abstract
A comprehensive research program with the long-term goal of discovering sustainable methods for drug target synthesis is proposed. Specifically, organocatalytic insertion reactions will be investigated. En route to realizing this goal, the objectives of this proposed research agenda include (i) exploring urea and phosphoric acid derivatives as catalysts for N-H and O-H insertion reactio...
- New synthetic methodologies for the construction of pyrrolidine, piperidine and indolizidine systems, AP.R
Abstract
Part of this project makes use of a,b-unsaturated diazoketones as potential bifunctional intermediates to be applied in the quick and efficient synthesis of various alkaloids. Among these we can mention piperidine, indolizidine and pyrrolidine alkaloids. Specifically, this project aims the use of these intermediates in the divergent synthesis of several polyhydroxilated alkaloids and th...
- Exploration of enantioselective transformations of diazoketones and Sulfoxonium ylides, BP.PD
Abstract
The research proposed provides a unified catalytic strategy using chiral Brønsted acids to access carbon-oxygen, carbon-nitrogen, carbon-sulfur and carbon-halogen bonds from either diazoketones or sulfoxonium ylides as starting materials.
- New methodologies using sulfur ylides for the enantioselective alpha-Heterofunctionalization of carbonyl compounds, BP.DD
Abstract
Alpha-heterofunctionalized carbonyl compounds have a wide versatility as synthetic building blocks, due to a variety of transformations that these can participate. However, there are a limited number of asymmetric methodologies to prepare this class of compounds. Therefore, the development of such methodologies is of great importance in the area of organic synthesis. Combining this need...
- Exploring the application of diazocarbonyl compounds and sulfur ylides in the asymmetric ring opening reactions with epoxides for the synthesis of oxetanes and functionalized alcohols, BP.DR
Abstract
A great challenge for synthetic organic chemists is ensuring molecular diversity and structural complexity in reaction products, carried out by selective methodologies with a few number of steps. The development of synthetic approaches that provide enantiomerically enriched compounds have attracted a continuous interest from both academia and industry, since different enantiomers of an ...
(Only some records are available in English at this moment)
- Synthesis of unsaturated bicyclic lactones via sulfur ylides, BP.IC
Abstract
This project aims to evaluate methodologies for the synthesis of unsaturated bicyclic lactones through the Corey-Chaykovsky reaction, followed by elimination-epoxide opening. The methodology to be evaluated has already been applied in our laboratory for the synthesis of the unsaturated bicyclic lactone 5,5-dimethyltetrahydroisocromen-3(4H)-one, in 35% yield. The project aims to optimize...
- Development of a new methodologies for synthesis of bicyclic aromatic ketones and naphthols employing diazoketones and Beta-keto sulfoxonium ylides, BP.MS
Abstract
The Friedel-Crafts acylation reaction is one of the most important methods for the formation of aromatic ketones. There are several methodologies already described in the literature to obtain this class of compounds. However, these synthetic routes are very similar to the classical method developed by Friedel and Crafts, which use quite a number of supra-stoichiometric reactive Lewis or...
- Thia-Michael additions and insertion reactions in a,b-unsaturated sulfur ylides, BP.IC
Abstract
Sulfur compounds are present in a wide array of natural and non natural products with relevant biological activity. Thus, these compounds have great importance in the medicinal, biochemical and synthetic areas. Tetrahydrothiophenes are sulfur heterocycles composed by a five atoms ring and are present in important bioactive compounds such as biotine. This class of compounds also presents...
(Only some records are available in English at this moment)
- Exploring noncovalent catalysis in enantioselective reactions with diazoketones and Sulfoxonium ylides, BE.EP.PD
Abstract
Our research group have been exploring the chemistry of a,b-unsaturated diazoketones and b-ketosulfoxonium ylides and using these compounds in several relevant chemical transformations. Currently, we are studying enantioselective reactions employing a,b-unsaturated diazoketones, aryl and alkyl diazoketones and b-ketosulfoxonium ylides. In this project, enantioselective reactions will be...
- Site-specific modification of proteins via aqueous Horner-Wadsworth-Emmons reaction followed by Wolff rearrangement, BE.EP.DR
Abstract
This project aims at applying the knowledge on the chemistry of alpha,beta-unsaturated diazoketones, developed in our group, to enable the site-selective modification of proteins in collaboration with Prof. Gonçalo Bernardes at University Of Cambridge, UK. Chemical protein modification has emerged as an invaluable tool for understanding natural systems, create therapeutic conjugates wit...
- Synthesis of Inimosugars with piperidine core from a,b-unsaturated diazoketones with Z geometry, BE.EP.MS
Abstract
This project aims at the use of a,b-unsaturated diazoketones with the Z geometry, developed in our group, to the synthesis of iminosugars with piperidine cores. This small organic molecules will be applied to demonstrate the relevance of therapeutic strategy SRT (Substrate Reduction Therapy) against Niemann-Pick disease (NPD), defined by the pathological lysosomal accumulation of sphing...
(Only some records are available in English at this moment)
| 2 / 2 | Ongoing research grants |
| 5 / 3 | Completed research grants |
| 5 / 5 | Ongoing scholarships in Brazil |
| 20 / 17 | Completed scholarships in Brazil |
| 5 / 5 | Completed scholarships abroad |
| 37 / 32 | All research grants and scholarships |
| Associated processes | |
(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)
| Publications | 32 |
| Citations | 354 |
| Cit./Article | 11.1 |
| Data from Web of Science | |
BURTOLOSO, ANTONIO C. B.; SANTIAGO, JOAO V.; BERNARDIM, BARBARA; TALERO, ALEXANDER G.. Advances in the Enantioselective Metal-catalyzed N-H and O-H Insertion Reactions with Diazocarbonyl Compounds. CURRENT ORGANIC SYNTHESIS, v. 12, n. 5, p. 650-659, 2015. Web of Science Citations: 6. (12/22274-2, 13/25504-1, 13/18009-4)
BURTOLOSO, ANTONIO C. B.; DIAS, RAFAEL M. P.; BERNARDIM, BARBARA. alpha,beta-Unsaturated Diazoketones as Useful Platforms in the Synthesis of Nitrogen Heterocycles. ACCOUNTS OF CHEMICAL RESEARCH, v. 48, n. 4, p. 921-934, APR 2015. Web of Science Citations: 35. (12/22274-2, 13/25504-1)
BERNARDIM, BARBARA; LORDELLO, LEONARDO D.; BURTOLOSO, ANTONIO C. B.. alpha,beta-Unsaturated Diazoketones as Versatile Building Blocks for the Synthesis of Hydroxylated Piperidines, Indolizidines and Quinolizidines. CURRENT TOPICS IN MEDICINAL CHEMISTRY, v. 13, n. 17, p. 2099-2103, SEP 2013. Web of Science Citations: 8. (12/04685-5)
BURTOLOSO, ANTONIO C. B.; BERTONHA, ARIANE F.; ROSSET, ISAC G.. Synthesis of Alkaloids: Recent Advances in the Synthesis of Phenanthroindolizidine Alkaloids. CURRENT TOPICS IN MEDICINAL CHEMISTRY, v. 14, n. 2, p. 191-199, JAN 2014. Web of Science Citations: 16. (10/18801-1, 12/04685-5, 11/15903-0)
ROSSET, ISAC G.; DIAS, RAFAEL M. P.; PINHO, VAGNER D.; BURTOLOSO, ANTONIO C. B.. Three-Step Synthesis of (+)-Preussin from Decanal. Journal of Organic Chemistry, v. 79, n. 14, p. 6748-6753, JUL 18 2014. Web of Science Citations: 15. (10/18801-1, 12/04685-5, 08/09653-9)
SGOBBI, LIVIA F.; PINHO, VAGNER 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, JUN 2013. Web of Science Citations: 4. (08/09653-9, 12/08750-6)
SANTOS, CAMILA S.; SOARES, CAIO C. S. P.; VIEIRA, ADRIANO S.; BURTOLOSO, ANTONIO C. B.. Synthesis of long-chain polyols from the Claisen condensation of gamma-valerolactone. GREEN CHEMISTRY, v. 21, n. 23, p. 6441-6450, DEC 7 2019. Web of Science Citations: 0. (17/23329-9)
GALLO, RAFAEL D. C.; CAMPOVILLA, JR., ORLANDO C.; AHMAD, ANEES; BURTOLOSO, ANTONIO C. B.. Synthesis of Oxazinanones: Intramolecular Cyclization of Amino Acid-Derived Diazoketones via Silica-Supported HClO4 Catalysis. FRONTIERS IN CHEMISTRY, v. 7, FEB 8 2019. Web of Science Citations: 1. (13/18009-4, 15/20084-0, 17/23329-9)
AMARANTE, GIOVANNI W.. Metal-Free Insertion Reactions of Diazo Carbonyls to Azlactones. Journal of Organic Chemistry, v. 83, n. 18, p. 11399-11406, SEP 21 2018. Web of Science Citations: 1. (13/18009-4, 17/23329-9)
SANTIAGO, JOAO VICTOR; BURTOLOSO, ANTONIO C. B.. Synthesis of Fused Bicyclic [1,2,3]-Triazoles from gamma-Amino Diazoketones. ACS OMEGA, v. 4, n. 1, p. 159-168, JAN 2019. Web of Science Citations: 0. (13/18009-4, 13/25504-1, 17/23329-9)
BURTOLOSO, ANTONIO C. B.; DIAS, RAFAEL M. P.; BERNARDIM, BARBARA. alpha,beta-Unsaturated Diazoketones as Useful Platforms in the Synthesis of Nitrogen Heterocycles. ACCOUNTS OF CHEMICAL RESEARCH, v. 48, n. 4, p. 921-934, APR 2015. Web of Science Citations: 35. (12/22274-2, 13/25504-1)
BURTOLOSO, ANTONIO C. B.; SANTIAGO, JOAO V.; BERNARDIM, BARBARA; TALERO, ALEXANDER G.. Advances in the Enantioselective Metal-catalyzed N-H and O-H Insertion Reactions with Diazocarbonyl Compounds. CURRENT ORGANIC SYNTHESIS, v. 12, n. 5, p. 650-659, 2015. Web of Science Citations: 6. (12/22274-2, 13/25504-1, 13/18009-4)
BERNARDIM, BARBARA; LORDELLO, LEONARDO D.; BURTOLOSO, ANTONIO C. B.. alpha,beta-Unsaturated Diazoketones as Versatile Building Blocks for the Synthesis of Hydroxylated Piperidines, Indolizidines and Quinolizidines. CURRENT TOPICS IN MEDICINAL CHEMISTRY, v. 13, n. 17, p. 2099-2103, SEP 2013. Web of Science Citations: 8. (12/04685-5)
CHUI, MEGAN; METZKER, GUSTAVO; BERNT, CHRISTOPHER M.; TRAN, ANTHONY T.; BURTOLOSO, ANTONIO C. B.; FORD, PETER C.. Probing the Lignin Disassembly Pathways with Modified Catalysts Based on Cu-Doped Porous Metal Oxides. ACS SUSTAINABLE CHEMISTRY & ENGINEERING, v. 5, n. 4, p. 3158-3169, APR 2017. Web of Science Citations: 12. (13/17271-7, 14/24552-5)
DIAS, RAFAEL M. P.; BURTOLOSO, ANTONIO C. B.. Catalyst-Free Insertion of Sulfoxonium Ylides into Aryl Thiols. A Direct Preparation of beta-Keto Thioethers. ORGANIC LETTERS, v. 18, n. 12, p. 3034-3037, JUN 17 2016. Web of Science Citations: 29. (13/18009-4, 13/25504-1)
BERNARDIM, BARBARA; COUCH, ERICA D.; HARDMAN-BALDWIN, ANDREA M.; BURTOLOSO, ANTONIO C. B.; MATTSON, ANITA E.. Divergent Roles of Urea and Phosphoric Acid Derived Catalysts in Reactions of Diazo Compounds. SYNTHESIS-STUTTGART, v. 48, n. 5, p. 677-686, MAR 2016. Web of Science Citations: 11. (13/18009-4, 13/25504-1, 13/50312-9, 12/22274-2)
AHMAD, ANEES; BURTOLOSO, ANTONIO C. B.. Total Synthesis of (+/-)-Brussonol and (+/-)-Komaroviquinone via a Regioselective Cross-Electrophile Coupling of Aryl Bromides and Epoxides. ORGANIC LETTERS, v. 21, n. 15, p. 6079-6083, AUG 2 2019. Web of Science Citations: 1. (13/18009-4, 15/20084-0, 17/23329-9)
DIAS, RAFAEL M. P.; MOMO, PATRICIA B.; BURTOLOSO, ANTONIO C. B.. One-step syntheses of substituted 2-pyrrolidinones and 3-pyrrolidinones from alpha,beta-unsaturated diazoketones and amines. Application in the synthesis of barmumycin. Tetrahedron, v. 73, n. 26, p. 3720-3729, JUN 29 2017. Web of Science Citations: 7. (13/18009-4, 13/25504-1, 15/22003-7)
BERNARDIM, BARBARA; CAL, PEDRO M. S. D.; MATOS, MARIA J.; OLIVEIRA, BRUNO L.; MARTINEZ-SAEZ, NURIA; ALBUQUERQUE, INES S.; PERKINS, ELIZABETH; CORZANA, FRANCISCO; BURTOLOSO, ANTONIO C. B.; JIMENEZ-OSES, GONZALO; et al. Stoichiometric and irreversible cysteine-selective protein modification using carbonylacrylic reagents. NATURE COMMUNICATIONS, v. 7, OCT 26 2016. Web of Science Citations: 31. (12/22274-2, 13/25504-1, 15/07509-1)
KAWAMURA, MEIRE Y.; TALERO, ALEXANDER G.; SANTIAGO, JOAO V.; GARAMBEL-VILCA, EDSON; ROSSET, ISAC G.; BURTOLOSO, ANTONIO C. B.. Six-Step Syntheses of (-)-1-Deoxyaltronojirimycin and (+)-1-Deoxymannonojirimycin from N-Z-O-TBDPS-L-serinal. Journal of Organic Chemistry, v. 81, n. 21, p. 10569-10575, NOV 4 2016. Web of Science Citations: 5. (13/18009-4, 13/25504-1, 13/26399-7)
METZKER, GUSTAVO; DIAS, RAFAEL M. P.; BURTOLOSO, ANTONIO C. B.. Iron-Catalyzed Reductive Amination from Levulinic and Formic Acid Aqueous Solutions: An Approach for the Selective Production of Pyrrolidones in Biorefinery Facilities. CHEMISTRYSELECT, v. 3, n. 2, p. 368-372, JAN 17 2018. Web of Science Citations: 8. (13/18009-4, 13/17271-7)
BURTOLOSO, ANTONIO C. B.; MOMO, PATRICIA B.; NOVAIS, GRAZIELE L.. Traditional and New methods for the Preparation of Diazocarbonyl Compounds. Anais da Academia Brasileira de Ciências, v. 90, n. 1, 1, p. 859-893, 2018. Web of Science Citations: 5. (13/18009-4, 13/25504-1, 15/22003-7)
TALERO, ALEXANDER G.; BURTOLOSO, ANTONIO C. B.. Sharpless Asymmetric Dihydroxylation on ,-Unsaturated Diazoketones: A New Entry for the Synthesis of Disubstituted Furanones. Synlett, v. 28, n. 14, p. 1748-1752, SEP 2017. Web of Science Citations: 5. (13/18009-4, 13/25504-1)
BERNARDIM, BARBARA; MATOS, MARIA J.; FERHATI, XHENTI; COMPANON, ISMAEL; GUERREIRO, ANA; AKKAPEDDI, PADMA; BURTOLOSO, ANTONIO C. B.; JIMENEZ-OSES, GONZALO; CORZANA, FRANCISCO; BERNARDES, GONCALO J. L.. Efficient and irreversible antibody-cysteine bioconjugation using carbonylacrylic reagents. Nature Protocols, v. 14, n. 1, p. 86-99, JAN 2019. Web of Science Citations: 2. (13/25504-1, 15/07509-1, 17/13168-8)
TALERO, ALEXANDER GARAY; MARTINS, BRUNA SIMOES; BURTOLOSO, ANTONIO C. B.. Coupling of Sulfoxonium Ylides with Arynes: A Direct Synthesis of Pro-Chiral Aryl Ketosulfoxonium Ylides and Its Application in the Preparation of alpha-Aryl Ketones. ORGANIC LETTERS, v. 20, n. 22, p. 7206-7211, NOV 16 2018. Web of Science Citations: 9. (13/18009-4, 17/02092-0, 17/23329-9)
METZKER, GUSTAVO; BURTOLOSO, ANTONIO C. B.. Conversion of levulinic acid into gamma-valerolactone using Fe-3(CO)(12): mimicking a biorefinery setting by exploiting crude liquors from biomass acid hydrolysis. CHEMICAL COMMUNICATIONS, v. 51, n. 75, p. 14199-14202, 2015. Web of Science Citations: 20. (13/25504-1, 13/17271-7)
BERNARDIM, BARBARA; BURTOLOSO, ANTONIO C. B.. A two-step synthesis of the bioprotective agent JP4-039 from N-Boc-L-leucinal. Tetrahedron, v. 70, n. 20, p. 3291-3296, MAY 20 2014. Web of Science Citations: 6. (12/22274-2, 09/54040-8, 12/04685-5)
BURTOLOSO, ANTONIO C. B.; DIAS, RAFAEL M. P.; LEONARCZYK, IVES A.. Sulfoxonium and Sulfonium Ylides as Diazocarbonyl Equivalents in Metal-Catalyzed Insertion Reactions. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2013, n. 23, p. 5005-5016, AUG 2013. Web of Science Citations: 44. (12/04685-5)
BERNARDIM, BARBARA; HARDMAN-BALDWIN, ANDREA M.; BURTOLOSO, ANTONIO C. B.. LED lighting as a simple, inexpensive, and sustainable alternative for Wolff rearrangements. RSC ADVANCES, v. 5, n. 18, p. 13311-13314, 2015. Web of Science Citations: 11. (12/22274-2, 13/25504-1)
ROSSET, ISAC G.; BURTOLOSO, ANTONIO 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, n. 18, p. 9464-9470, SEP 20 2013. Web of Science Citations: 11. (10/18801-1, 12/04685-5)
SANTOS, CAMILA S.; BURTOLOSO, ANTONIO C. B.. Direct Synthesis of Highly Substituted Cyclopentadienes and Derivatives from the Self-Condensation of Renewable Ethyl Levulinate. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2018, n. 45, p. 6350-6354, DEC 6 2018. Web of Science Citations: 1. (17/23329-9)
MATOS, MARIA J.; NAVO, CLAUDIO D.; HAKALA, TUULI; FERHATI, XHENTI; GUERREIRO, ANA; HARTMANN, DAVID; BERNARDIM, BARBARA; SAAR, KADI L.; COMPANON, ISMAEL; CORZANA, FRANCISCO; et al. Quaternization of Vinyl/Alkynyl Pyridine Enables Ultrafast Cysteine-Selective Protein Modification and Charge Modulation. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v. 58, n. 20, p. 6640-6644, MAY 13 2019. Web of Science Citations: 1. (15/07509-1, 17/13168-8)
(References retrieved automatically from State of São Paulo Research Institutions)
SOUZA, Barbara Bernardim de. Novas metodologias em síntese orgânica empregando o rearranjo de Wolff em diazocetonas insaturadas. 2017. Tese (Doutorado) – Instituto de Química de São Carlos. Universidade de São Paulo (USP). São Carlos.
BURTOLOSO, Antonio Carlos Bender. 3-azetidinonas e 3-azetidinois : preparação e aplicações na sintese de azetidinas substituidas. 2006. Tese (Doutorado) – Instituto de Quimica. Universidade Estadual de Campinas.
BERTONHA, Ariane Fernandes. Construção do esqueleto 6-aril indolizidínico a partir de α-clorocetonas derivadas da (S)-prolina: síntese da (S)-desoxiipalbidina. 2014. Dissertação (Mestrado) - Instituto de Química de São Carlos. Universidade de São Paulo (USP). São Carlos.
ROSSET, Isac George. Diazocetonas α,β-insaturadas como reagentes multifuncionais: aplicação na síntese de alcaloides piperidínicos e pirrolidínicos. 2015. Tese (Doutorado) – Instituto de Química de São Carlos. Universidade de São Paulo (USP). São Carlos.
PEREIRA, Rafael Fonseca. Estudos visando à síntese do tripanossomicida (±)-komaroviquinona. 2011. Dissertação (Mestrado) - Instituto de Química de São Carlos. Universidade de São Paulo (USP). São Carlos.
KAWAMURA, Meire Yasuko. Emprego de diazocetonas α,β-insaturadas com geometria Z na direta construção de esqueletos indolizidínicos e piperidínicos funcionalizados. 2016. Dissertação (Mestrado) - Instituto de Química de São Carlos. Universidade de São Paulo (USP). São Carlos.
PINHO, Vagner Dantas. Abordagens divergentes na preparação de alcaloides indolizidínicos. 2013. Tese (Doutorado) – Instituto de Química de São Carlos. Universidade de São Paulo (USP). São Carlos.