Synthesis of 1,4,6-Tricarbonyl Compounds via Regioselective Gold(I)-Catalyzed Alkyne Hydration and Their Application in the Synthesis of alpha-Arylidene-butyrolactones

Autor(es)

Lima, Samia R. ^[1] ; Coelho, Fernando ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Lab Synth Nat Prod & Drugs, Inst Chem, BR-13083970 Campinas, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: ACS OMEGA; v. 5, n. 14, p. 8032-8045, APR 14 2020.
• Citações Web of Science: 0

Resumo

We report a direct, straightforward, and regioselective hydration of 1,4-enynes designed from Morita-Baylis- Hillman adducts. Under smooth conditions and short reaction times, gold-catalyzed hydration of internal alkynes provides synthetically useful ketones as single regioisomers in yields higher than 90%. The synthetic usefulness of this protocol was demonstrated by the conversion of selected ketones into biologically valuable alpha-alkylidene-gamma-lactones upon reduction with sodium borohydride. In the course of the scope evaluation, we discovered that this methodology could also furnish alpha-arylidene-beta,gamma-butenolides. (AU)

• Processo FAPESP: 18/02611-0 - A pós-Funcionalização de Pequenas Moléculas Poli-funcionalizadas: Uma Abordagem Robusta para a Síntese de Novos Padrões Estruturais com Potencial Atividade Biológica
• Beneficiário: Fernando Antonio Santos Coelho
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• 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