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

• Grant number: 17/23329-9
• Support type: Regular Research Grants
• Duration: April 01, 2018 - June 30, 2020
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal researcher: Antonio Carlos Bender Burtoloso
• Grantee: Antonio Carlos Bender Burtoloso
• Home 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)

Scientific publications

(13)

(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)

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, DEC 17 2021. (17/23329-9, 19/12300-5, 20/07147-0)

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, JUL 7 2020. (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, DEC 18 2020. (17/23329-9, 18/17800-3, 13/18009-4)

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. (13/18009-4, 13/25504-1, 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. (17/23329-9, 15/20084-0, 13/18009-4)

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, SEP 7 2018. (17/23329-9, 13/18009-4)

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. (17/23329-9)

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. (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. (17/23329-9, 13/18009-4)

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. (17/23329-9, 13/18009-4, 17/02092-0)

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, MAY 2020. (17/23329-9, 18/19105-0, 13/18009-4)

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, JUN 5 2020. (09/54040-8, 13/50228-8, 17/23837-4, 17/23329-9)

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. (17/23329-9, 15/20084-0, 13/18009-4)