A(3)- Coupling Reaction as a Strategy Towards the Synthesis of Alkaloids

Author(s)

Carmona, Rafaela C. ^[1] ; Wendler, Edison P. ^[1] ; Sakae, George H. ^[1] ; Comasseto, Joao V. ^{[2, 1]} ; Dos Santos, Alcindo A. ^[1]

Affiliation

^[1] Univ Sao Paulo, Inst Quim, BR-05508000 Sao Paulo - Brazil

^[2] Univ Fed Sao Paulo, Inst Ciencias Ambientais Quim & Farmaceut, BR-09972270 Diadema, SP - Brazil

• Document type: Journal article
• Source: Journal of the Brazilian Chemical Society; v. 26, n. 1, p. 117-123, JAN 2015.
• Web of Science Citations: 5

Abstract

A number of aldehydes, alkynols and benzylamines were submitted to A(3)-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 five- and 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: 08/55401-1 - Preparation and application of chiral compounds containing chalcogens
• Grantee: João Valdir Comasseto
• Support Opportunities: Research Projects - Thematic Grants
• 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