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Synthesis of substituted cyclopentanes and long chain polyols from abundant chemical platforms derived from biomass

Grant number: 17/23329-9
Support Opportunities:Regular Research Grants
Start date: April 01, 2018
End date: June 30, 2020
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Antonio Carlos Bender Burtoloso
Grantee:Antonio Carlos Bender Burtoloso
Host Institution: Instituto de Química de São Carlos (IQSC). Universidade de São Paulo (USP). São Carlos , SP, Brazil

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 (levulinic acid and its esters, gamma-valerolactone and angelica lactones). Thus, the present project aims at the use of biomass building blocks for the total synthesis of organic molecules with high added value, including cyclopentanes and substituted cyclopentadienes as well as long chain polyols. (AU)

Articles published in Agência FAPESP Newsletter about the research grant:
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VEICULO: TITULO (DATA)
VEICULO: TITULO (DATA)

Scientific publications (18)
(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)
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, . (15/20084-0, 17/23329-9, 13/18009-4)
DIAS, RAFAEL MAFRA P.; DE OLIVEIRA, GABRIELA P.; BURTOLOSO, ANTONIO C. B.. One-pot synthesis of beta-O-4 lignin modelsviathe insertion of stable 2-diazo-1,3-dicarbonyls into O-H bonds. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 18, n. 25, p. 4815-4823, . (17/23329-9)
FURNIEL, LUCAS G.; BURTOLOSO, ANTONIO C. B.. Copper-catalyzed N-H insertion reactions from sulfoxonium ylides. Tetrahedron, v. 76, n. 51, SI, . (13/18009-4, 17/23329-9, 18/17800-3)
AMARANTE, GIOVANNI W.. Metal-Free Insertion Reactions of Diazo Carbonyls to Azlactones. Journal of Organic Chemistry, v. 83, n. 18, p. 11399-11406, . (17/23329-9, 13/18009-4)
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, . (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, . (13/18009-4, 13/25504-1, 17/23329-9)
GALLO, RAFAEL DOUGLAS C.; BURTOLOSO, ANTONIO C. B.. Silica-supported HClO4 promotes catalytic solvent- and metal-free O-H insertion reactions with diazo compounds. GREEN CHEMISTRY, v. 20, n. 19, p. 4547-4556, . (17/23329-9, 13/18009-4)
LEVEILLE, ALEXANDRIA N.; ECHEMENDIA, RADELL; MATTSON, ANITA E.; BURTOLOSO, ANTONIO C. B.. nantioselective Indole Insertion Reactions of alpha-Carbonyl Sulfoxonium Ylide. ORGANIC LETTERS, v. 23, n. 24, p. 9446-9450, . (20/07147-0, 17/23329-9, 19/12300-5)
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, . (17/23329-9)
MOMO, PATRICIA B.; MIZOBUCHI, EDUARDO F.; ECHEMENDIA, RADELL; BADDELEY, ISABEL; GRAYSON, MATTHEW N.; BURTOLOSO, ANTONIO C. B.. Organocatalytic Enantioselective Sulfa-Michael Additions to alpha,beta-Unsaturated Diazoketones. Journal of Organic Chemistry, v. 87, n. 5, p. 9-pg., . (19/12300-5, 20/07147-0, 17/23329-9, 18/02920-3, 15/22003-7)
FURNIEL, LUCAS G.; BURTOLOSO, ANTONIO C. B.. Copper-catalyzed N-H insertion reactions from sulfoxonium ylides. Tetrahedron, v. 76, n. 51, p. 10-pg., . (17/23329-9, 18/17800-3, 13/18009-4)
DIAS, RAFAEL MAFRA P.; DE OLIVEIRA, GABRIELA P.; BURTOLOSO, ANTONIO C. B.. One-pot synthesis of beta-O-4 lignin models via the insertion of stable 2-diazo-1,3-dicarbonyls into O-H bonds. ORGANIC & BIOMOLECULAR CHEMISTRY, v. 18, n. 25, p. 9-pg., . (17/23329-9)
ECHEMENDIA, RADELL; DE OLIVEIRA, KLEBER T.; BURTOLOSO, ANTONIO C. B.. Visible-Light-Promoted Synthesis of 1,3-Dicarbonyl Sulfoxonium Ylides. ORGANIC LETTERS, v. 24, n. 35, p. 5-pg., . (19/27176-8, 17/23329-9, 20/06874-6, 19/12300-5, 13/07276-1, 20/07147-0)
MOMO, PATRICIA B.; LEVEILLE, ALEXANDRIA N.; FARRAR, ELLIOT H. E.; GRAYSON, MATTHEW N.; MATTSON, ANITA E.; BURTOLOSO, ANTONIO C. B.. Enantioselective S-H Insertion Reactions of alpha-Carbonyl Sulfoxonium Ylides. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v. 59, n. 36, . (18/19105-0, 13/18009-4, 17/23329-9)
CAIUBY, CLARICE A. D.; DE JESUS, MATHEUS P.; BURTOLOSO, ANTONIO C. B.. alpha-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles. Journal of Organic Chemistry, v. 85, n. 11, p. 7433-7445, . (09/54040-8, 13/50228-8, 17/23837-4, 17/23329-9)
GALLO, RAFAEL D. C.; CAMPOVILLA, ORLANDO C., JR.; AHMAD, ANEES; BURTOLOSO, ANTONIO C. B.. Synthesis of Oxazinanones: Intramolecular Cyclization of Amino Acid-Derived Diazoketones via Silica-Supported HClO4 Catalysis. RONTIERS IN CHEMISTR, v. 7, p. 7-pg., . (13/18009-4, 15/20084-0, 17/23329-9)
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, . (17/02092-0, 17/23329-9, 13/18009-4)

Filed patent(s) as a result of this research project

PROCESSO DE SÍNTESE DE POLIÓIS DE CADEIA LONGA A PARTIR DE BIOMASSA E COMPOSTOS OBTIDOS BR1020200216694 - Universidade de São Paulo (USP) . ANTONIO CARLOS BENDER BURTOLOSO / CAMILA SOUZA SANTOS / ADRIANO SIQUEIRA VIEIRA / CAIO CÉSAR DOS SANTOS PENTEADO SOARES - October 2020, 22