Highly Stereoselective Synthesis of trans -Dihydronarciclasine Analogues

Gábor Varró, Lenke Mattyasovszky, A. Grün, András Simon, L. Hegedûs, István Kádas

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Several new trans -dihydronarciclasine analogues were stereo selectively synthesised by applying our feasible and efficient process developed recently. These new phenanthridone alkaloid derivatives were obtained in both racemic and optically active forms. During their enantioselective syntheses, high selectivities (up to 99% ee) were achieved by using (8 S,9 S)-9-amino(9-deoxy)epiquinine as an organocatalyst. The modifications, the introduction of ethoxy or methoxy groups, were made in ring A of the phenanthridone scaffold.

Original languageEnglish
Article numberss-2017-t0559-op
Pages (from-to)625-643
Number of pages19
JournalSynthesis (Germany)
Volume50
Issue number3
DOIs
Publication statusPublished - Feb 1 2018

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Keywords

  • alkaloids
  • organocatalysis
  • phenanthridone scaffold
  • stereoselective synthesis
  • trans -dihydronarciclasine analogues

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Varró, G., Mattyasovszky, L., Grün, A., Simon, A., Hegedûs, L., & Kádas, I. (2018). Highly Stereoselective Synthesis of trans -Dihydronarciclasine Analogues. Synthesis (Germany), 50(3), 625-643. [ss-2017-t0559-op]. https://doi.org/10.1055/s-0036-1591514