Abstract
The synthesis of N-methoxyascorbigen (neoascorbigen) — a natural substance from plants of the Cruciferae family — and also N-ethoxyascorbigen is described. In an acidic media under drastic conditions N-alkoxyascorbigens undergo transformations with the release of ascorbic acid and the formation of oligomers of 1-alkoxy-3-methyleneindolenine or with opening of the lactone ring, decarboxylation, and dehydration and the formation of 2-hydroxy-3-(1-alkoxy-3-indolyl)-4-hydroxymethylcyclopent-2-enone. Amides of neoascorbigen, 3-O-methylglycoside of N-ethoxyascorbigen, and the product of the reduction of N-ethoxyascorbigen by sodium borohydride were obtained for the first time.
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Additional information
Scientific-Research Institute of the Search for New Antibiotics, Russian Academy of Medical Sciences, Moscow. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 178–186, February, 2000.
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Yudina, L.N., Korolev, A.M., Reznikova, M.I. et al. Investigation of neoascorbigen. Chem Heterocycl Compd 36, 144–151 (2000). https://doi.org/10.1007/BF02283542
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DOI: https://doi.org/10.1007/BF02283542