ArticleOrganic letters2016
Total Synthesis of Macrocarpines D and E via an Enolate-Driven Copper-Mediated Cross-Coupling Process: Replacement of Catalytic Palladium with Copper Iodide.
Article in Organic letters, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed.
- First Total Synthesis of the Unnatural (+)-Talcarpine and (-)‑ACS omega · 2026Article
- Completion of the Total Synthesis of Several Bioactive Sarpagine/Macroline Alkaloids including the Important NF-κB InhibitorMolecules (Basel, Switzerland) · 2022Article
- Structure units oriented approach towards collective synthesis of sarpagine-ajmaline-koumine type alkaloids.Nature communications · 2022Article
- Bisindole Alkaloids from theMolecules (Basel, Switzerland) · 2021Review
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5 authors.
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Abstract
An enolate driven copper-mediated cross-coupling process enabled cheaper and greener access to the key pentacyclic intermediates required for the enantiospecific total synthesis of a number of C-19 methyl substituted sarpagine/macroline indole alkaloids. Replacement of palladium (60-68%) with copper iodide (82-89%) resulted in much higher yields. The formation of an unusual 7-membered cross-coupling product was completely inhibited by using TEMPO as a radical scavenger. Further functionalization led to the first enantiospecific total synthesis of macrocarpines D and E.
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