AI Article Synopsis
- Marine alkaloids caulibugulones A-D were synthesized in six steps from 2,5-dimethoxybenzaldehyde, showing an efficient pathway for obtaining these compounds.
- The synthesis involved a Pomeranz-Fritsch reaction that led to the formation of 5,8-dimethoxyisoquinoline, which was then oxidized to isoquinolinediones using N-haloimides.
- The final step involved aminolysis with methylamine or ethanolamine, resulting in a 24-57% yield of the target alkaloids.
Article 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.
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| http://dx.doi.org/10.1021/jo302772t | DOI Listing |
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