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.
2-hydroxy-3-(1-alkoxy-3-indolyl)-4-hydroxymethylcyclopent-2-enones, neoascorbigen, N-ethoxyascorbigen
Publication DOI: 10.1007/BF02283542Journal NLM ID: 0050006Publisher: New York: Kluwer Academic/Plenum Publishers
Institutions: Scientific-Research Institute of the Search for New Antibiotics, Russian Academy of Medical Sciences, Moscow, Russia
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