Palladium-Catalyzed Formation of Substituted Tetrahydropyrans: Mechanistic Insights and Structural Revision of Natural Products

Autor(es)

Della-Felice, Franco ^[1] ; de Assis, Francisco F. ^[1] ; Sarotti, Ariel M. ^[2] ; Pilli, Ronaldo A. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Inst Chem, BR-13084971 Campinas, SP - Brazil

^[2] Univ Nacl Rosario CONICET, Fac Ciencias Bioquim & Farmaceut, Inst Quim Rosario, Suipacha 531, S2002 LRK, Rosario, Santa Fe - Argentina

• Tipo de documento: Artigo Científico
• Fonte: SYNTHESIS-STUTTGART; v. 51, n. 7, p. 1545-1560, APR 2019.
• Citações Web of Science: 0

Resumo

A comprehensive study on the stereochemical outcome of palladium-catalyzed formation of 2,4,6-trisubstituted tetrahydropyrans through cyclization of the corresponding allylic acetates using both Pd(0) and Pd(II) catalysts is presented. We have found that the stereochemical outcome of this cyclization is dependent not only on the stereochemistry of the acyclic precursor but also on the nature of the palladium catalyst. These results were applied to the total synthesis of the putative structure of cryptoconcatone H. Experimental and computational DP4+ NMR results were used to assess the structures proposed for cryptoconcatones K and L. (AU)

• Processo FAPESP: 13/07607-8 - CMPO - Centro Multidisciplinar de Pesquisa em Obesidade e Doenças Associadas
• Beneficiário: Licio Augusto Velloso
• Linha de fomento: Auxílio à Pesquisa - Centros de Pesquisa, Inovação e Difusão - CEPIDs
• Processo FAPESP: 16/12541-4 - Abordagem biomimética para a síntese de alcalóides Stemona
• Beneficiário: Ronaldo Aloise Pilli
• Linha de fomento: Auxílio à Pesquisa - Regular
• Processo FAPESP: 14/25474-8 - Síntese e avaliação biológica da Brevipolida A, Criptomoscatona F1 e de compostos relacionados
• Beneficiário: Franco Della Felice
• Linha de fomento: Bolsas no Brasil - Doutorado Direto