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Type: Artigo de periódico
Title: Exploitation of a Tuned Oxidation with N-Haloimides in the Synthesis of Caulibugulones A-D
Author: Naciuk, FF
Milan, JC
Andreao, A
Miranda, PCML
Abstract: 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.
Country: EUA
Editor: Amer Chemical Soc
Citation: Journal Of Organic Chemistry. Amer Chemical Soc, v. 78, n. 10, n. 5026, n. 5030, 2013.
Rights: fechado
Identifier DOI: 10.1021/jo302772t
Date Issue: 2013
Appears in Collections:Unicamp - Artigos e Outros Documentos

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