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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 F.F.
Milan J.C.
Andreao A.
Miranda P.C.M.L.
Abstract: Marine alkaloids caulibugulones A-D were synthesized in six steps starting from the readily available 2,5-dimethoxybenzaldehyde. Pomeranz-Fritsch reaction of N-(2,5-dimethoxybenzyl)-N-(2,2-dimethoxyethyl)-2-nitrobenzenesulfonamide proceeded smoothly to give 5,8-dimethoxyisoquinoline, which was oxidized to isoquinolinediones 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. © 2013 American Chemical Society.
Rights: fechado
Identifier DOI: 10.1021/jo302772t
Date Issue: 2013
Appears in Collections:Unicamp - Artigos e Outros Documentos

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