Synthesis of drugs and bioactive substances from Baylis-Hillman adducts: 1) synthesis of 4-fluoroquinolonic acid class antibiotics; 2) asymmetric synthesis of antiinflammatory DFP

• Grant number: 05/02373-2
• Support Opportunities: Scholarships in Brazil - Doctorate
• Start date: January 01, 2006
• End date: August 31, 2009
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Fernando Antonio Santos Coelho
• Grantee: Giovanni Wilson Amarante
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil

Abstract

This PhD project has as main objective the development of new synthetic approaches to the preparation of antibiotics derived from acid 4-fluorquinolonic and also the synthesis of an anti-inflammatory agent (DFP),using the Baylis-Hillman as substrates. This project is part of a research strategy which has the following goals: 1) the development of new approaches for the preparation of bioactive compounds and drugs; 2)demonstrate the synthetic versatility iof the Baylis-Hillman adducts, as substrate for the synthesis of commercially and therapeutically valuable compounds.

Scientific publications

(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)

AMARANTE‚ G.W.; REZENDE‚ P.; CAVALLARO‚ M.; COELHO‚ F.. Acyloins from Morita-Baylis-Hillman adducts: an alternative approach to the racemic total synthesis of bupropion. Tetrahedron Letters, v. 49, n. 23, p. 3744-3748, 2008. (06/06347-9, 05/02373-2)

PORTO, RICARDO S.; AMARANTE, GIOVANNI W.; CAVALLARO, MAYRA; POPPI, RONEI J.; COELHO, FERNANDO. Improved catalysis of Morita-Baylis-Hillman reaction. The strong synergic effect using both an imidazolic ionic liquid and a temperature. Tetrahedron Letters, v. 50, n. 11, p. 1184-1187, MAR 18 2009. (06/06347-9, 05/02373-2)

Academic Publications

(References retrieved automatically from State of São Paulo Research Institutions)

AMARANTE, Giovanni Wilson. The Morita-Baylis-Hillman reaction in organic chemistry. 1-Mechanistic studies by mass spectrometry. 2-Synthesis of drugs, diastereoselective synthesis of 1,2-aminoalcohols via Curtis rearrangement. 2009. Doctoral Thesis - Universidade Estadual de Campinas (UNICAMP). Instituto de Química Campinas, SP.