ArticleAngewandte Chemie (International ed. in English)2022
Total Synthesis of the Tetracyclic Pyridinium Alkaloid epi-Tetradehydrohalicyclamine B.
Article in Angewandte Chemie (International ed. in English), 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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15 citing papers in PubMed.
- Proposed Biosynthesis and Molecular Targets of Manzamine Alkaloids fromMarine drugs · 2026Article
- Total Synthesis of Voratin C: Formation of the [6,5]-Spiroketal Core through Acid-Mediated Epoxide Cascade Opening.Organic letters · 2026Article
- Enantioselective Total Synthesis of Two Aromatized Halicyclamines.Journal of the American Chemical Society · 2026Article
- Harnessing Photochemistry in Natural Product Synthesis: From Strategy to Applications.Journal of natural products · 2025Review
- Collective Total Synthesis of a Unique Class of Liverworts-Derived Cembrane Diterpenoids.Angewandte Chemie (International ed. in English) · 2025Article
- Tetracyclic Bis-Piperidine Alkaloids: Structures, Bioinspired Synthesis, Synthesis, and Bioactivities.Molecules (Basel, Switzerland) · 2025Review
- Total Synthesis of the Norcembranoid Scabrolide B and Its Transformation into Sinuscalide C, Ineleganolide, and Horiolide.Journal of the American Chemical Society · 2024Article
- 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
- Catalytic enantioselective reductive alkynylation of amides enables one-pot syntheses of pyrrolidine, piperidine and indolizidine alkaloids.Nature communications · 2023Article
- Total Synthesis of Njaoamine C by Concurrent Macrocycle Formation.Journal of the American Chemical Society · 2023Article
- Revisiting the manzamine biosynthetic hypothesis.Natural product reports · 2023Review
- Base-Induced Sulfoxide-Sulfenate Rearrangement of 2-Sulfinyl Dienes for the Regio- and Stereoselective Synthesis of Enantioenriched Dienyl Diols.The Journal of organic chemistry · 2023Article
- Total Synthesis of the Tetracyclic Pyridinium Alkaloid epi-Tetradehydrohalicyclamine B.Angewandte Chemie (International ed. in English) · 2022Article
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3 authors.
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Abstract
The first total synthesis of a tetracyclic marine pyridinium alkaloid hinged on recent advances in chemoselectivity management: While many classical methods failed to afford the perceptively simple pyridine-containing core of the target, nickel/iridium photoredox dual catalysis allowed the critical C-C bond to be formed in good yield. Likewise, ring closing alkyne metathesis (RCAM) worked well in the presence of the unhindered pyridine despite the innately Lewis acidic Mo(+6) center of the alkylidyne catalyst. Finally, an iridium catalyzed hydrosilylation was uniquely effective in reducing a tertiary amide without compromising an adjacent pyridine and the lateral double bonds; this transformation is largely without precedent. The second strained macrocycle enveloping the core was closed by intramolecular N-alkylation with formation of the pyridinium unit; the reaction proceeded site- and chemoselectively in the presence of an a priori more basic tertiary amine.
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