Exploitation of a Tuned Oxidation with N-Haloimides in the Synthesis of Caulibugulones A-D

Autor(es)

Naciuk, Fabricio F. ^[1] ; Milan, Julio C. ^[1] ; Andreao, Almir ^[2] ; Miranda, Paulo C. M. L. ^[1]

Afiliação do(s) autor(es)

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

^[2] IFES, Aracruz, ES - Brazil

• Tipo de documento: Artigo Científico
• Fonte: Journal of Organic Chemistry; v. 78, n. 10, p. 5026-5030, MAY 17 2013.
• Citações Web of Science: 7

Resumo

Marine alkaloids caulibugulones A-D were synthesized in six steps starting from the readily available 2,5-dimethoxybenzaldehyde. Pomeranz-Fritsch reaction of N-(2,S-dimethoxybenzyl)-N-(2,2-dimethoxyethyl)-2-nitrobenzenesulfonamide proceeded smoothly to give 5,8-dimethoxyisoquinoline, which was oxidized to isoquinolinadiones by a tunable oxidation reaction with N-haloimides. Therefore, NBS furnished direct conversion to the isoquinoline-5,8-dione; alternatively, N-haloimides of cyanuric acid provided both oxidation and halogenation generating 6,7-dihaloisoquinoline-5,8-diones. Aminolyses of these isoquinolinediones with methylamine or ethanolamine produced the isoquinolinedione alkaloids caulibugulones A-D in 24-57% overall yield. (AU)

• Processo FAPESP: 09/51602-5 - Biologia química: novos alvos moleculares naturais e sintéticos contra o câncer, estudos estruturais, avaliação biológica e modo de ação
• Beneficiário: Ronaldo Aloise Pilli
• Modalidade de apoio: Auxílio à Pesquisa - Temático