ArticleAngewandte Chemie (International ed. in English)2023
A Divergent Polyene Cyclization for the Total Synthesis of Greenwayodendrines, Greenwaylactams, Polysin and Polyveoline.
Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- A General Approach toJournal of the American Chemical Society · 2026Article
- Stereodivergent Synthesis of Perhydrobenz[Journal of the American Chemical Society · 2025Article
- Reusable Selenenyl Iodide-Initiated Cascade Cyclization of Polyenes with N-terminating Groups.Chemistry, an Asian journal · 2025Article
- Highlights from the 57th Bürgenstock Conference on Stereochemistry 2024.Chemical science · 2024Article
- Natural Product Synthesis: The Endless Quest for Unreachable Perfection.ACS organic & inorganic Au · 2023Review
- A biomimetic approach for the concise total synthesis of greenwaylactams A-C.Organic & biomolecular chemistry · 2023Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
We present a concise asymmetric total synthesis (5-8 steps) of nine sesquiterpenoid alkaloids featuring four different tetra-/pentacyclic scaffolds. To this end, a novel, bioinspired indole N-terminated cationic tricyclization has been developed, enabling the divergent synthesis of greenwayodendrines and polysin. Subtle variation of the C2-substituted indole cyclization precursor allowed switching between indole N- and C-termination. For the latter, a subsequent Witkop oxidation enabled conversion of the cyclopentene-fused indole into the eight-membered benzolactam to directly furnish the family of greenwaylactams. In addition, a diastereomeric C-termination product has been elaborated to provide access to polyveoline.
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Registered trials
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