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(Referência obtida automaticamente do Web of Science, por meio da informação sobre o financiamento pela FAPESP e o número do processo correspondente, incluída na publicação pelos autores.)

Multicomponent Synthesis of Cyclic Depsipeptide Mimics by Ugi Reaction Including Cyclic Hemiacetals Derived from Asymmetric Organocatalysis

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Autor(es):
de la Torre, Alexander F. [1] ; Rivera, Daniel G. [1, 2] ; Concepcion, Odette [2] ; Echemendia, Radell [1, 2] ; Correa, Arlene G. [1] ; Paixao, Marcio W. [1]
Número total de Autores: 6
Afiliação do(s) autor(es):
[1] Univ Fed Sao Carlos, Dept Quim, BR-13565905 Sao Carlos, SP - Brazil
[2] Univ Havana, Fac Chem, Ctr Nat Prod Res, Havana 10400 - Cuba
Número total de Afiliações: 2
Tipo de documento: Artigo Científico
Fonte: Journal of Organic Chemistry; v. 81, n. 3, p. 803-809, FEB 5 2016.
Citações Web of Science: 13
Resumo

The synthesis of novel cyclic depsipeptide mimics by means of an organocatalytic conjugate addition, leading to chiral cyclic hemiacetals, followed by a multi component reaction with alpha-amino acids and isocyanides, is described. The initial organocatalytic step is employed for the asymmetric derivatization of alpha,beta-unsaturated aldehydes to 4,5-disubstituted 2-hydroxytetrahydropyrans, which are next used as chiral bifunctional substrates on the Ugi five-center three component reaction, giving rise to nine-membered-ring lactones. This sequential approach proved to be suitable for the rapid generation of molecular complexity through the combination of aliphatic, dipeptidic, glucosidic, and lipidic isocyanides with several amino acids, thus giving access to amido-, glyco-, and lipo-depsipeptide scaffolds featuring natural product-like structures. (AU)

Processo FAPESP: 15/17141-1 - Desenvolvimento e Estudos Mecanísticos de Novas Metodologias Sintéticas para Síntese de Compostos Bioativos
Beneficiário:Ricardo Samuel Schwab
Modalidade de apoio: Auxílio à Pesquisa - Regular
Processo FAPESP: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
Beneficiário:Arlene Gonçalves Corrêa
Modalidade de apoio: Auxílio à Pesquisa - Programa Centros de Pesquisa em Engenharia