ArticleJournal of the American Chemical Society2019
Total Synthesis of Pentacyclic (-)-Ambiguine P Using Sequential Indole Functionalizations.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Regiospecific α-arylation of diverse carbonyl compounds using an organobismuth transporter.Nature chemistry · 2026Article
- An Organometallic Umpolung Approach for Iron-Mediated Propargylic C-H Etherification.Angewandte Chemie (International ed. in English) · 2024Article
- Construction of C2-indolyl-quaternary centers by branch-selective allylation: enabling concise total synthesis of the (±)-mersicarpine alkaloid.Chemical science · 2024Article
- Dearomative (4 + 3) Cycloaddition Reactions of 3-Alkenylindoles and 3-Alkenylpyrroles to Afford Cyclohepta[Organic letters · 2022Article
- Recent advances in hapalindole-type cyanobacterial alkaloids: biosynthesis, synthesis, and biological activity.Natural product reports · 2021Review
- Total Synthesis of the Chlorinated Pentacyclic Indole Alkaloid (+)-Ambiguine G.Journal of the American Chemical Society · 2021Article
- Structural diversification of hapalindole and fischerindole natural products via cascade biocatalysis.ACS catalysis · 2021Article
- An invocation for computational evaluation of isomerization transforms: cationic skeletal reorganizations as a case study.Natural product reports · 2021Review
- Oxodealkenylative Cleavage of Alkene C(spAngewandte Chemie (International ed. in English) · 2020Article
- Unraveling Plant Natural Chemical Diversity for Drug Discovery Purposes.Frontiers in pharmacology · 2020Review
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Authors and funding
6 authors.
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Abstract
The first synthesis of a pentacyclic ambiguine (ambiguine P) is reported. The synthesis takes advantage of sequential alkylations of an indole core to rapidly construct the pentacyclic framework of the natural product. Key to the success of the synthesis was the use of a Nicholas reaction to alkylate at C2, crafting a fused seven-membered ring that is characteristic of the pentacyclic ambiguines, as well as the use of an amide-directed functionalization at C12 to set a requisite quaternary center. A versatile late-stage intermediate was prepared that may be applicable to the synthesis of the other pentacyclic ambiguines.
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