ArticleJournal of the American Chemical Society2023
Total Synthesis of Njaoamine C by Concurrent Macrocycle Formation.
Article in Journal of the American Chemical Society, 2023. 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.
- Total Synthesis of Benthol A: The Nominal and the Actual Natural Product.Journal of the American Chemical Society · 2026Article
- Enantioselective Synthesis ofJACS Au · 2026Article
- Square-Planar Ruthenium Alkylidyne Complexes Undergo Stepwise Rather Than Concerted [2 + 2] Cycloadditions with Alkynes.Angewandte Chemie (International ed. in English) · 2026Article
- Collective Total Synthesis of a Unique Class of Liverworts-Derived Cembrane Diterpenoids.Angewandte Chemie (International ed. in English) · 2025Article
- Oxoammonium-Catalyzed Oxidation ofJournal of the American Chemical Society · 2024Article
- Total Synthesis of the Norcembranoid Scabrolide B and Its Transformation into Sinuscalide C, Ineleganolide, and Horiolide.Journal of the American Chemical Society · 2024Article
- Review
- Molybdenum(VI) Nitrido Complexes with Tripodal Silanolate Ligands. Structure and Electronic Character of an Unsymmetrical Dimolybdenum μ-Nitrido Complex Formed by Incomplete Nitrogen Atom Transfer.Inorganic chemistry · 2024Article
- Total Synthesis of the Allenic Macrolide (+)-Archangiumide.Journal of the American Chemical Society · 2024Article
- From the Glovebox to the Benchtop: Air-Stable High Performance Molybdenum Alkylidyne Catalysts for Alkyne Metathesis.Journal of the American Chemical Society · 2023Article
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Authors and funding
3 authors.
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Abstract
In conceptual terms, the first total synthesis of the cytotoxic marine natural product njaoamine C differs from all known approaches toward related alkaloids of the manzamine superfamily in that both macrocyclic rings enveloping the diazatricyclic core are concomitantly formed; this goal was reached by double ring closing alkyne metathesis (dRCAM). The success of this maneuver does not merely reflect a favorable preorientation of the four alkyne chains that need to be concatenated in the proper pairwise manner but is also the outcome of dynamic covalent chemistry involving error correction by the chosen "canopy" molybdenum alkylidyne catalyst. The end game downstream of dRCAM capitalizes on the striking chemoselectivity of palladium-catalyzed hydrostannation, which selects for (hetero)arylalkynes even in the presence of sterically much more accessible dialkylalkynes or alkenes; for this preference, the method complements the classical repertoire of hydrometalation and semireduction reactions.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.