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

• Grant number: 13/10449-5
• Support Opportunities: Regular Research Grants
• Start date: May 01, 2014
• End date: July 31, 2016
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Fernando Antonio Santos Coelho
• Grantee: Fernando Antonio Santos Coelho
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• City of the host institution: Campinas

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)

Scientific publications

(14)

(The scientific publications listed on this page originate from the Web of Science or SciELO databases. Their authors have cited FAPESP grant or fellowship project numbers awarded to Principal Investigators or Fellowship Recipients, whether or not they are among the authors. This information is collected automatically and retrieved directly from those bibliometric databases.)

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. (13/10449-5, 12/10701-3)

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. (13/10449-5, 13/06757-6, 16/09579-0, 13/07600-3)

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. (13/10449-5, 14/02062-6, 13/07600-3)

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. (13/10449-5, 13/07600-3)

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. (15/09205-0, 13/10449-5, 13/07600-3)

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, v. 2016, n. 11, p. 5-pg., 2016-04-01. (12/21809-0, 13/24386-5, 13/07600-3, 13/10449-5)

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. (13/24386-5, 13/10449-5, 12/21809-0, 13/07600-3)

SILVA, THIAGO S.; CORREIA, JOSE T. M.; PISCELLI, BRUNO A.; CORMANICH, RODRIGO A.; LIST, BENJAMIN; COELHO, FERNANDO. Catalyst-Dependent Asymmetric Dearomative and Desymmetrizative Higher-Order [8+2] Cycloaddition of Indolizines with Maleimides toward the Atroposelective Synthesis of Cyclazines. ACS CATALYSIS, v. 15, n. 15, p. 10-pg., 2025-07-22. (23/14064-2, 18/03910-1, 13/07600-3, 14/02062-6, 13/10449-5, 23/18007-3, 12/21809-0)

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. (13/10449-5, 13/07600-3)

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. (13/10449-5, 10/04716-2, 13/07600-3)

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. (13/10449-5, 15/01491-3, 13/07600-3, 13/22235-0)

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. (13/10449-5, 12/08048-0)

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. (15/09205-0, 13/10449-5, 13/07600-3)

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. (13/10449-5, 13/18203-5)

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