INVESTIGATION OF NEOASCORBIGEN

Authors

  • Л. Н. Юдина Scientific-Research Institute of the Search for New Antibiotics, Russian Academy of Medical Sciences
  • А. М. Королев Scientific-Research Institute of the Search for New Antibiotics, Russian Academy of Medical Sciences
  • М. И. Резникова Scientific-Research Institute of the Search for New Antibiotics, Russian Academy of Medical Sciences
  • М. Н. Преображенская Scientific-Research Institute of the Search for New Antibiotics, Russian Academy of Medical Sciences

DOI:

https://doi.org/10.1007/43

Keywords:

2-hydroxy-3-(1-alkoxy-3-indolyl)-4-hydroxymethylcyclopent-2-enones, neoascorbigen, N–ethoxyascorbigen

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.

Authors: L. N. Yudina, A. M. Korolev, M. I. Reznikova, and M. N. Preobrazhenskaya.

English Translation in Chemistry of Heterocyclic Compounds, 2000, 36 (2), pp 144-151

http://link.springer.com/article/10.1007/BF02283542

Downloads

Published

2012-11-16

Issue

No. 2 (2000)

Section

Original Papers