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

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 enan...

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Detalles Bibliográficos
Autores principales: Varró, Gábor, Pogrányi, Balázs, Grün, Alajos, Simon, András, Hegedűs, László, Kádas, István
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2018
Materias:
Original Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7087796/
https://www.ncbi.nlm.nih.gov/pubmed/32214482
http://dx.doi.org/10.1007/s00706-018-2287-7
Descripción
Sumario: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: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s00706-018-2287-7) contains supplementary material, which is available to authorized users.

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