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Total Syntheses of (−)‐Minovincine and (−)‐Aspidofractinine through a Sequence of Cascade Reactions

We report 8‐step syntheses of (−)‐minovincine and (−)‐aspidofractinine using easily available and inexpensive reagents and catalyst. A key element of the strategy was the utilization of a sequence of cascade reactions to rapidly construct the penta‐ and hexacyclic frameworks. These cascade transform...

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Detalles Bibliográficos
Autores principales: Varga, Szilárd, Angyal, Péter, Martin, Gábor, Egyed, Orsolya, Holczbauer, Tamás, Soós, Tibor
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7497198/
https://www.ncbi.nlm.nih.gov/pubmed/32351014
http://dx.doi.org/10.1002/anie.202004769
Descripción
Sumario:We report 8‐step syntheses of (−)‐minovincine and (−)‐aspidofractinine using easily available and inexpensive reagents and catalyst. A key element of the strategy was the utilization of a sequence of cascade reactions to rapidly construct the penta‐ and hexacyclic frameworks. These cascade transformations included organocatalytic Michael‐aldol condensation, a multistep anionic Michael‐S(N)2 cascade reaction, and Mannich reaction interrupted Fischer indolization. To streamline the synthetic routes, we also investigated the deliberate use of steric effect to secure various chemo‐ and regioselective transformations.