Carbonylative Coupling and Intramolecular Cycloaddition [2 + 2] Reactions Employing D-Glucal

• Grant number: 17/24821-4
• Support Opportunities: Regular Research Grants
• Start date: March 01, 2018
• End date: February 29, 2020
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Helio Alexandre Stefani
• Grantee: Helio Alexandre Stefani
• Host Institution: Faculdade de Ciências Farmacêuticas (FCF). Universidade de São Paulo (USP). São Paulo , SP, Brazil

Abstract

The main focus of the project is the use of 3,4,6-tri-O-acetyl-D-glucal for use in transformations involving carbonyl coupling reactions (Sonogashira, Suzuki-Miyaura and Stille), selenosugars, and intermolecular [2+2] cycloaddition. It is also intended to evaluate the biological activity of the compounds prepared (e.g. antifungal, anticancer and anti-inflammatory activity). (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)

DARBEM, MARIANA P.; KANNO, KARINA S.; DE OLIVEIRA, ISADORA M.; ESTEVES, C. HENRIQUE A.; PIMENTA, DANIEL C.; STEFANI, HELIO A.. Synthesis of amidoglucals and glucal esters via carbonylative coupling reactions of 2-iodoglucal using Mo(CO)(6) as a CO source. NEW JOURNAL OF CHEMISTRY, v. 43, n. 2, p. 696-699, JAN 14 2019. (17/26673-2, 17/24821-4, 16/04289-3, 16/24396-9)

VASCONCELOS, STANLEY N. S.; REIS, JOEL S.; DE OLIVEIRA, ISADORA M.; BALFOUR, MICHAEL N.; STEFANI, HELIO A.. Synthesis of symmetrical biaryl compounds by homocoupling reaction. Tetrahedron, v. 75, n. 13, p. 1865-1959, MAR 29 2019. (13/17960-7, 16/04289-3, 17/24821-4, 14/19221-0, 16/02392-1)

REIS, JOEL S.; FERNANDES, ARTHUR B.; FREITAS-DORR, BARBARA C.; BASTOS, ERICK L.; STEFANI, HELIO A.. Oxazoline as acceptor moiety for excited-state intramolecular proton transfer. Tetrahedron, v. 74, n. 48, p. 6866-6872, NOV 29 2018. (14/22136-4, 15/25629-4, 14/10563-5, 17/24821-4, 16/02392-1, 16/21445-9)

DARBEM, MARIANA P.; ESTEVES, HENRIQUE A.; DE OLIVEIRA, ISADORA M.; PIMENTA, DANIEL C.; STEFANI, HELIO A.. Palladium-Catalyzed Thio- and Selenocarbonylation of 2-Iodoglycals. CHEMCATCHEM, v. 12, n. 2, NOV 2019. (16/24396-9, 16/04289-3, 17/26673-2, 17/24821-4)

DARBEM, MARIANA P.; ESTEVES, C. HENRIQUE A.; DE OLIVEIRA, ISADORA M.; REIS, JOEL S.; PIMENTA, DANIEL C.; STEFANI, HELIO A.. Synthesis of d-glyco-alkynone derivatives via carbonylative Sonogashira reaction. RSC ADVANCES, v. 9, n. 17, p. 9468-9474, 2019. (17/26673-2, 16/04289-3, 17/24821-4, 16/02392-1, 16/24396-9)

ESTEVES, HENRIQUE A.; DARBEM, MARIANA P.; PIMENTA, DANIEL C.; STEFANI, HELIO A.. Carbonylative Negishi-Type Coupling of 2-Iodoglycals with Alkyl and Aryl Halides. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2019, n. 44, p. 7384-7388, NOV 30 2019. (17/26673-2, 17/24821-4, 16/24396-9)

DE OLIVEIRA, ISADORA M.; ESTEVES, HENRIQUE A.; DARBEM, MARIANA P.; SARTORELLI, ARTHUR; CORRERA, THIAGO C.; RODRIGUES-OLIVEIRA, ANDRE F.; PIMENTA, DANIEL C.; ZUKERMAN-SCHPECTOR, JULIO; MANARIN, FLAVIA; STEFANI, HELIO A.. Stereo- and Regioselective Cu-Catalyzed Hydroboration of Alkynyl Chalcogenoethers. CHEMCATCHEM, v. 12, n. 13, MAY 2020. (16/04289-3, 14/50316-7, 17/24821-4, 16/24396-9, 17/26673-2)

SOARES-PAULINO, ANTONIO AUGUSTO; STEFANI, HELIO A.. Synthesis of Diverse C2-Glyco-Acyl Azides and -Ureas by Palladium-Catalyzed Carbonylation Coupling of 2-Iodoglycals. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2020, n. 25, JUN 2020. (14/50316-7, 18/10108-7, 17/24821-4)

DARBEM, MARIANA P.; ESTEVES, HENRIQUE A.; DE OLIVEIRA, ISADORA M.; STEFANI, HELIO A.. alpha,beta-Unsaturated 2-Ketoglycosides via Pd-Catalyzed Carbonylative Heck Reaction of 2-Iodoglycals. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, v. 2020, n. 32, JUL 2020. (16/24396-9, 16/04289-3, 17/26673-2, 14/50316-7, 17/24821-4)

DE OLIVEIRA, ISADORA M.; ESTEVES, C. HENRIQUE A.; DARBEM, MARIANA P.; PIMENTA, DANIEL C.; ZUKERMAN-SCHPECTOR, JULIO; FERREIRA, ANTONIO G.; STEFANI, HELIO A.; MANARIN, FLAVIA. Iron (III)-Promoted Synthesis of Substituted 4H-Chalcogenochromenes and Chemoselective Functionalization. ADVANCED SYNTHESIS & CATALYSIS, v. 361, n. 13, p. 3163-3172, JUL 2 2019. (17/26673-2, 17/24821-4, 16/04289-3, 16/24396-9)

SANTOS, FABIANO S.; ZANOTTO, GABRIEL M.; ARGOMEDO, LUIS M. Z.; DARBEM, MARIANA P.; GONCALVES, PAULO F. B.; STEFANI, HELIO A.; RODEMBUSCH, FABIANO S.. Synthesis, experimental and theoretical photophysical study of proton transfer based oxazoline fluorophores. Potential tailor made optical sensors for enantiomeric detection in solution. DYES AND PIGMENTS, v. 165, p. 372-382, JUN 2019. (16/24396-9, 17/24821-4)

COSTA, CLAUDIA A.; LOPES, RAYSSA M.; FERRAZ, LETICIA S.; ESTEVES, GABRIELA N. N.; DI IORIO, JULIANA F.; SOUZA, ALINE A.; DE OLIVEIRA, ISADORA M.; MANARIN, FLAVIA; JUDICE, WAGNER A. S.; STEFANI, HELIO A.; et al. Cytotoxicity of 4-substituted quinoline derivatives: Anticancer and antileishmanial potential. Bioorganic & Medicinal Chemistry, v. 28, n. 11, JUN 1 2020. (16/04289-3, 18/25747-5, 16/25112-4, 17/24821-4, 14/02205-1)

BALFOUR, MICHAEL N.; ZUKERMAN-SCHPECTOR, JULIO; DAVILA RODRIGUEZ, MARIA JOSE; REIS, JOEL SAVI; ESTEVES, CARLOS HENRIQUE A.; STEFANI, HELIO A.. Combination of Sonogashira coupling and 5-endo-dig cyclization for the synthesis of 2,6-disubstituted-5-azaindoles. Synthetic Communications, v. 49, n. 3, p. 351-358, FEB 1 2019. (14/19221-0, 16/02392-1, 17/26673-2, 17/24821-4)