Straightforward Synthesis of Isoellipticine by Palladium-Catalysed Coupling Reactions

Autor(es)

Naciuk, Fabricio F. ^{[1, 2]} ; Castro, Joaquim A. M. ^[1] ; Serikava, Bruno K. ^[1] ; Miranda, Paulo C. M. L. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Estadual Campinas, Inst Quim, BR-13083970 Campinas, SP - Brazil

^[2] CNPEM, LNBio, Brazilian Ctr Res Energy & Mat, BR-13083970 Campinas, SP - Brazil

• Tipo de documento: Artigo Científico
• Fonte: CHEMISTRYSELECT; v. 3, n. 2, p. 436-439, JAN 17 2018.
• Citações Web of Science: 2

Resumo

Our novel synthetic route to isoellipticine featured palladium-catalyzed intramolecular reactions for the construction of the B ring of the pyridocarbazole nucleus. The adequate palladium-catalyzed reaction depended upon the oxidation conditions that were applied in order to prepare the immediate synthetic precursor. When CAN was used to make the quinone intermediate, an oxidative cyclization through a double C-H bond activation was applied. Conversely, when the oxidation condition involved TCCA as oxidant, a direct C-H arylation was employed. Both approaches showed similar efficiencies in order to construct the pyridocarbazole nucleus. Isoellipticine was prepared in only 5 steps with a 21%-23% overall yield. (AU)

• Processo FAPESP: 14/25770-6 - Novas fronteiras em reações de acoplamento cruzado mediadas por paládio: associando catálise enantiosseletiva, ativações C-H, novos materiais e reações em fluxo visando alta eficiência e sustentabilidade em processos sintéticos
• Beneficiário: Carlos Roque Duarte Correia
• Modalidade de apoio: Auxílio à Pesquisa - Temático