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Morita-Baylis-Hillman adducts as efficient building blocks for the synthesis of molecules of biological interest

Abstract

This research has as main target the exploitation of the Morita-Baylis-Hillman adducts as efficient building blocks for the synthesis of molecules of biological interest. The project was divided into two parts. In the first one, we intend to plan, synthesize and evaluated the biological profile of new substances with potential antifungal activity. These new substances were designed based on the theoretical models, available in the literature, for the prediction of antifungal activity. The second project has as main proposal exploiting the synthetic potentiality of intermediates, prepared from Morita-Baylis-Hillman adducts, as substrate for an intramolecular nucleophilic substitution or benzoinic condensation mediated by N-heterocyclic carbenes. The cyclic product obtained in the intramolecular nucleophilc substitution step will be used as substrate for the stereoselective synthesis of alkaloids such as pumiliotoxin, homopumiliotoxin and allopumiliotoxin. (AU)

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Scientific publications (12)
(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)
AGY, ANDRE CAPRETZ; RODRIGUES, JR., MANOEL T.; ZEOLY, LUCAS A.; SIMONI, DEBORAH A.; COELHO, FERNANDO. Palladium-Mediated Oxidative Annulation of delta-Indolyl-alpha,beta-Unsaturated Compounds toward the Synthesis of Cyclopenta[b]indoles and Heterogeneous Hydrogenation To Access Fused Indolines. Journal of Organic Chemistry, v. 84, n. 9, p. 5564-5581, MAY 3 2019. Web of Science Citations: 4.
GOMES, RALPH C.; SAKATA, RENATA P.; ALMEIDA, WANDA P.; COELHO, FERNANDO. Spirocyclohexadienones as an Uncommon Scaffold for Acetylcholinesterase Inhibitory Activity. Medicinal Chemistry, v. 15, n. 4, p. 373-382, 2019. Web of Science Citations: 1.
RAICH, LLUIS; SANTOS, HUGO; GOMES, JULIANA C.; RODRIGUES, JR., MANOEL T.; GALAVERNA, RENAN; EBERLIN, MARCOS N.; COELHO, FERNANDO; ROVIRA, CARME; MOYANO, ALBERT. Can an Alcohol Act As an Acid/Base Catalyst in Water Solution? An Experimental and Theoretical Study of Imidazole Catalysis of the Aqueous Morita-Baylis--Hillman Reaction. ACS CATALYSIS, v. 8, n. 3, p. 1703-1714, MAR 2018. Web of Science Citations: 5.
DA SILVA, ERICA C.; YAMAKAWA, NATHALIA C. G.; DOS SANTOS, ALCINDO A.; COELHO, FERNANDO. Short and Diastereoselective Total Synthesis of the Polyhydroxylated Pyrrolidine LAB-1: A Potent -Glycosidase Inhibitor. SYNTHESIS-STUTTGART, v. 49, n. 21, p. 4869-4875, NOV 2017. Web of Science Citations: 3.
MENEZES CORREIA, JOSE TIAGO; LIST, BENJAMIN; COELHO, FERNANDO. Catalytic Asymmetric Conjugate Addition of Indolizines to alpha,beta-Unsaturated Ketones. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, v. 56, n. 27, p. 7967-7970, JUN 26 2017. Web of Science Citations: 34.
GOMES, RALPH C.; BARCELOS, ROSIMEIRE C.; RODRIGUES, JR., MANOEL T.; SANTOS, HUGO; COELHO, FERNANDO. Intermolecular Stetter Reactions on Morita-Baylis-Hillman Adducts: an Approach to Highly Functionalized 1,4-Dicarbonyl Compounds. CHEMISTRYSELECT, v. 2, n. 3, p. 926-930, JAN 2017. Web of Science Citations: 1.
SANTOS, MARILIA S.; FERNANDES, DANIARA C.; RODRIGUES, JR., MANOEL T.; REGIANI, THAIS; ANDRICOPULO, ADRIANO D.; RUIZ, ANA LUCIA T. G.; VENDRAMINI-COSTA, DEBORA B.; DE CARVALHO, JOAO E.; EBERLIN, MARCOS N.; COELHO, FERNANDO. Diastereoselective Synthesis of Biologically Active Cyclopenta[b]indoles. Journal of Organic Chemistry, v. 81, n. 15, p. 6626-6639, AUG 5 2016. Web of Science Citations: 10.
DE LIMA BATISTA, ANA P.; COELHO, FERNANDO; BRAGA, ATAUALPA A. C. DFT exploration of mechanistic pathways of an aza-Morita-Baylis-Hillman reaction. THEORETICAL CHEMISTRY ACCOUNTS, v. 135, n. 8 JUL 12 2016. Web of Science Citations: 5.
CORREIA, JOSE TIAGO M.; ACCONCIA, LAIS V.; COELHO, FERNANDO. Studies on Pumiliotoxin A Alkaloids: An Approach to Preparing the Indolizidinic Core by Intramolecular Diastereoselective N-Heterocyclic Carbene Catalyzed Benzoin Reaction. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, n. 11, p. 1972-1976, APR 2016. Web of Science Citations: 6.
GALAVERNA, RENAN; CAMILO, NILTON S.; GODOI, MARLA N.; COELHO, FERNANDO; EBERLIN, MARCOS N. Charge Tags for Most Comprehensive ESI-MS Monitoring of Morita-Baylis-Hillman (MBH)/aza-MBH Reactions: Solid Mechanistic View and the Dualistic Role of the Charge Tagged Acrylate. Journal of Organic Chemistry, v. 81, n. 3, p. 1089-1098, FEB 5 2016. Web of Science Citations: 8.
GUIDOTTI, BRUNO B.; COELHO, FERNANDO. Sequential Morita-Baylis-Hillman/Achmatowicz reactions: an expeditious access to pyran-3(6H)-ones with a unique substitution pattern. Tetrahedron Letters, v. 56, n. 46, p. 6356-6359, NOV 18 2015. Web of Science Citations: 2.
SANTOS, MARILIA S.; COELHO, FERNANDO; LIMA-JUNIOR, CLAUDIO G.; VASCONCELLOS, MARIO L. A. A. The Morita-Baylis-Hillman Reaction: Advances and Contributions from Brazilian Chemistry. CURRENT ORGANIC SYNTHESIS, v. 12, n. 6, p. 830-852, 2015. Web of Science Citations: 12.

Please report errors in scientific publications list by writing to: cdi@fapesp.br.
Filed patent(s) as a result of this research project

COMPOSTO COM ATIVIDADE ANTIFÚNGICA, PROCESSO DE SÍNTESE DO COMPOSTO, E USO DO COMPOSTO BR1020170180131 - Universidade Estadual de Campinas (UNICAMP) . Marilia Simão Dos Santos; Fernando Antônio Santos Coelho; Angélica Zaninelli Schreiber; Luzia Lyra Fernandes; João Ernesto De Carvalho; Ana Lucia Tasca Gois Ruiz - August 2017, 23