Journal
ORGANIC LETTERS
Volume 22, Issue 12, Pages 4675-4679Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c01472
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Funding
- National Research, Development and Innovation Office [FK 124863, K 125385]
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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 Aspidosperma 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-Nacetylcylindrocarine and the formal total synthesis of (-)-1-acetylaspidoalbidine.
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