A3-Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids

Author(s)

Rafaela C. Carmona ^[1] ; Edison P. Wendler ^[2] ; George H. Sakae ^[3] ; João V. Comasseto ; Alcindo A. Dos Santos ^[5]

Affiliation

^[1] Universidade de São Paulo. Instituto de Química - Brasil

^[2] Universidade de São Paulo. Instituto de Química - Brasil

^[3] Universidade de São Paulo. Instituto de Química - Brasil

^[5] Universidade de São Paulo. Instituto de Química - Brasil

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 26, n. 1, p. 117-123, 2015-01-00.

Abstract

A number of aldehydes, alkynols and benzylamines were submitted to A3-coupling reaction, under CuCl catalysis, giving strategically functionalized hydroxy-propargylamines. The procedure allows the use of alkyl as well as aryl aldehydes. Representative substrates were converted into fiveand six-membered cyclic alkaloids by sequential one-pot N-debenzylation/triple bond reduction promoted by Pd, followed by a Mitsunobu-type cyclization. (AU)

• FAPESP's process: 11/03244-2 - Asymmetric strategies in A-3 coupling eactions
• Grantee: Rafaela Costa Carmona
• Support Opportunities: Scholarships in Brazil - Master
• FAPESP's process: 11/11613-8 - A3-coupling reactions on the synthesis of bioactive nitrogen containing compounds
• Grantee: Alcindo Aparecido dos Santos
• Support Opportunities: Regular Research Grants
• FAPESP's process: 08/55401-1 - Preparation and application of chiral compounds containing chalcogens
• Grantee: João Valdir Comasseto
• Support Opportunities: Research Projects - Thematic Grants