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A3-Coupling Reactions on the Synthesis of Codonopsinine and Monomorine I

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


AbstractThis project aims applying coupling reaction of aldehydes, amines and alkynes (A3) on the synthesis of the two natural occurring alkaloids, codonopsinine and monomorine I. The A3 reaction is a power 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 alkynols. 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 pirrolidine of Codonopisinine and Monomorine I, respectively. For this end, experimental conditions previously developed by other students of the group will be applied.

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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)
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. Web of Science Citations: 3.
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. Web of Science Citations: 8.
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. Web of Science Citations: 9.

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