Organocatalysed synthesis of indolizidinic and quinolizidinic N-heterocycles from Morita-Baylis-Hillman adducts

• Grant number: 12/21809-0
• Support Opportunities: Scholarships in Brazil - Doctorate
• Start date: March 01, 2013
• End date: July 31, 2017
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Fernando Antonio Santos Coelho
• Grantee: José Tiago Menezes Correia
• Host Institution: Instituto de Química (IQ). Universidade Estadual de Campinas (UNICAMP). Campinas , SP, Brazil
• Associated scholarship(s): 14/02062-6 - Exploring the ACDC concept on hydrogenation and Friedel-Crafts reactions using indolizines obtained from Morita-Baylis-Hillman adducts, BE.EP.DR

Abstract

This PhD 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.

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)

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)

TEODORO, BRUNO V. M.; CORREIA, JOSE TIAGO M.; COELHO, FERNANDO. Selective Hydrogenation of Indolizines: An Expeditious Approach To Derive Tetrahydroindolizines and Indolizidines from Morita-Baylis-Hillman Adducts. Journal of Organic Chemistry, v. 80, n. 5, p. 2529-2538, MAR 6 2015. (12/21809-0, 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)

Academic Publications

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

CORREIA, José Tiago Menezes. Organocatalytic diastereo and enantioselective strategies for the synthesis and functionalization of N-heterocycles. 2017. Doctoral Thesis - Universidade Estadual de Campinas (UNICAMP). Instituto de Química Campinas, SP.