Highly Stereoselective Synthesis of Natural-Product-Like Hybrids by an Organocatalytic/Multicomponent Reaction Sequence

Autor(es)

Echemendia, Radell ^[1] ; de La Torre, Alexander F. ^[2] ; Monteiro, Julia L. ^[2] ; Pila, Michel ^[1] ; Correa, Arlene G. ^[2] ; Westermann, Bernhard ^{[3, 4]} ; Rivera, Daniel G. ^[1] ; Paixao, Marcio W. ^[2]

Afiliação do(s) autor(es)

^[1] Univ Havana, Ctr Nat Prod Res, Fac Chem, Havana 10400 - Cuba

^[2] Univ Fed Sao Carlos, Dept Quim, BR-97105900 Sao Carlos, SP - Brazil

^[3] Univ Halle Wittenberg, Inst Chem, D-06120 Halle - Germany

^[4] Leibniz Inst Plant Biochem, Dept Bioorgan Chem, D-06120 Halle, Saale - Germany

• Tipo de documento: Artigo Científico
• Fonte: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION; v. 54, n. 26, p. 7621-7625, JUN 22 2015.
• Citações Web of Science: 29

Resumo

In an endeavor to provide an efficient route to natural product hybrids, described herein is an efficient, highly stereoselective, one-pot process comprising an organocatalytic conjugate addition of 1,3-dicarbonyls to ,-unsaturated aldehydes followed by an intramolecular isocyanide-based multicomponent reaction. This approach enables the rapid assembly of complex natural product hybrids including up to four different molecular fragments, such as hydroquinolinone, chromene, piperidine, peptide, lipid, and glycoside moieties. The strategy combines the stereocontrol of organocatalysis with the diversity-generating character of multicomponent reactions, thus leading to structurally unique peptidomimetics integrating heterocyclic, lipidic, and sugar moieties. (AU)

• Processo FAPESP: 13/21599-8 - Estratégias para síntese de produtos naturais e análogos com atividade anti-cancerígena envolvendo reações multi-componentes organocatalisadas
• Beneficiário: Arlene Gonçalves Corrêa
• Modalidade de apoio: Auxílio à Pesquisa - Pesquisador Visitante - Internacional