Asymmetric synthesis of new gamma-butenolides via organocatalyzed epoxidation of chalcones

Autor(es)

Vieira, Lucas C. C. ; Matsuo, Bianca T. ; Martelli, Lorena S. R. ; Gall, Mayara ; Paixao, Marcio W. ; Correa, Arlene G.

• Tipo de documento: Artigo Científico
• Fonte: ORGANIC & BIOMOLECULAR CHEMISTRY; v. 15, n. 29, p. 6098-6103, AUG 7 2017.
• Citações Web of Science: 3

Resumo

gamma-Butenolides have been recognized as an important structural framework in a number of natural products and medicinally important agents. In this work we describe a new metal-free sequential strategy for the asymmetric synthesis of substituted gamma-butenolides having epoxychalcones as the advanced intermediate. Using the optimized reaction conditions, we were able to carry out the three-step sequence, epoxidation, olefination and hydrolysis, with only one single chromatographic purification of the final product, furnishing new enantiomerically enriched gamma-butenolides in moderate overall yield and good enantiomeric excess. (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
• Processo FAPESP: 13/07600-3 - CIBFar - Centro de Inovação em Biodiversidade e Fármacos
• Beneficiário: Glaucius Oliva
• Modalidade de apoio: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs