A3-Coupling reactions on the synthesis of Codonopsinine and Monomorine I

• Grant number: 12/17093-9
• Support Opportunities: Scholarships in Brazil - Scientific Initiation
• Start date: November 01, 2012
• End date: November 30, 2014
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Alcindo Aparecido dos Santos
• Grantee: João Luiz Petrarca de Albuquerque
• Host Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil

Abstract

This project aims to apply the coupling reaction of aldehydes, amines, and alkynes (A3) on the synthesis of the two naturally occurring alkaloids, codonopsinine, and monoamine I. An A3 reaction is a powerful tool for the carbon-carbon and carbon-heteroatom bond formation allowing the preparation of functionalized skeletons of great synthetic utility. The proposal is centered in the coupling of an organometallic generated in situ from a terminal alkynol and a metal salt or complex, and a nitrogen-containing electrophile (also generated in situ from an amine and an aldehyde resulting in an imine or an iminium salt). In previous investigations, we prepared some hydroxy-propargylamines by the A3-coupling reaction of aldehydes, amines, and alkanols. For this particular study, appropriated aldehydes will be prepared in order to obtain A3 coupling products possessing carbon skeleton strategically functionalized allowing two cyclizations via the nitrogen atom of the propargylamine produced from the A3 coupling reaction, and in this way allowing the preparation of the indolizidine skeleton indolizidine and pyrrolidine of Codonopisinine and Monomorine I, respectively. To this end, experimental conditions previously developed by other students of the group will be applied.(AU)

Scientific publications

(4)

(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)

CARMONA, RAFAELA C.; SCHEVCIW, EVELYN P.; PETRARCA DE ALBUQUERQUE, JOAO L.; WENDLER, EDISON P.; DOS SANTOS, ALCINDO A.. Joint use of microwave and glycerol-zinc (II) acetate catalytic system in the synthesis of 2-pyridyl-2-oxazolines. GREEN PROCESSING AND SYNTHESIS, v. 2, n. 1, p. 8-pg., 2013-02-01. (08/55401-1, 11/11613-8, 11/03244-2, 12/17093-9)

CARMONA, RAFAELA C.; SCHEVCIW, EVELYN P.; PETRARCA DE ALBUQUERQUE, JOAO L.; WENDLER, EDISON P.; DOS SANTOS, ALCINDO A.. Joint use of microwave and glycerol-zinc (II) acetate catalytic system in the synthesis of 2-pyridyl-2-oxazolines. GREEN PROCESSING AND SYNTHESIS, v. 2, n. 1, SI, p. 35-42, FEB 2013. (08/55401-1, 12/17093-9, 11/11613-8, 11/03244-2)

DONATONI, MARIA C.; JUNIOR, GILMAR A. B.; DE OLIVEIRA, KLEBER T.; ANDO, ROMULO A.; BROCKSOM, TIMOTHY J.; DOS SANTOS, ALCINDO A.. Solvent-free Diels-Alder reactions catalyzed by FeCl3 on Aerosil((R)) silica. Tetrahedron, v. 70, n. 20, p. 3231-3238, MAY 20 2014. (08/55401-1, 12/17093-9, 13/06532-4, 11/13993-2, 11/11613-8, 11/03244-2)

REIS DE SA, LEANDRO FIGUEIRA; TOLEDO, FABIANO TRAVANCA; DE SOUSA, BRUNO ARTUR; GONCALVES, AUGUSTO CESAR; TESSIS, ANA CLAUDIA; WENDLER, EDISON P.; COMASSETO, JOAO V.; DOS SANTOS, ALCINDO A.; FERREIRA-PEREIRA, ANTONIO. Synthetic organotelluride compounds induce the reversal of Pdr5p mediated fluconazole resistance in Saccharomyces cerevisiae. BMC Microbiology, v. 14, JUL 26 2014. (08/55401-1, 12/17093-9, 11/11613-8, 11/03244-2)