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.
News published in Agência FAPESP Newsletter about the scholarship: