Total Syntheses of Dihydroindole Aspidosperma Alkaloids: Reductive Interrupted Fischer Indolization Followed by Redox Diversification

We report a novel reductive interrupted Fischer indolization process for the concise assembly of the 20-oxoaspidospermidine framework. This rapid complexity generating route paves the way toward various dihydroindole alkaloids with different C-5 side chain redox patterns. The end-game redox modulati...

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Bibliographic Details
Published in:Organic letters 2020-06, Vol.22 (12), p.4675-4679
Main Authors: Martin, Gábor, Angyal, Péter, Egyed, Orsolya, Varga, Szilárd, Soós, Tibor
Format: Article
Language:English
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Letter
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Summary:We report a novel reductive interrupted Fischer indolization process for the concise assembly of the 20-oxoaspidospermidine framework. This rapid complexity generating route paves the way toward various dihydroindole alkaloids with different C-5 side chain redox patterns. The end-game redox modulations were accomplished by modified Wolff-Kishner reaction and photo-Wolff rearrangement, enabling the total synthesis of (-)-aspidospermidine, (-)-limaspermidine, and (+)-17-demethoxy- -acetylcylindrocarine and the formal total synthesis of (-)-1-acetylaspidoalbidine.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01472