Stereoselective synthesis of trans-dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety

Gábor Varró, Balázs Pogrányi, Alajos Grün, András Simon, László Hegedűs, István Kádas

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Abstract

Abstract: Some new trans-dihydronarciclasine derivatives containing a 1,4-benzodioxane moiety were stereoselectively synthesised using our feasible and efficient method developed recently. These new phenanthridone alkaloid analogues were obtained in both racemic and optically active forms. High enantioselectivities (up to 99% ee) were achieved by applying (8S,9S)-9-amino(9-deoxy)epiquinine as an organocatalyst. Due to a side reaction, various methoxyphenanthridine regioisomers were also prepared which afforded further synthetic trans-dihydronarciclasine analogues modified in the ring A of the phenanthridone scaffold. Graphical abstract: [Figure not available: see fulltext.].

Original languageEnglish
Pages (from-to)2265-2285
Number of pages21
JournalMonatshefte fur Chemie
Volume149
Issue number12
DOIs
Publication statusPublished - Dec 1 2018

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Keywords

  • Alkaloids
  • Antitumor agents
  • Heterocycles
  • Organocatalysis
  • Total synthesis

ASJC Scopus subject areas

  • Chemistry(all)

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