ArticleOrganic letters2014
Biosynthetically inspired divergent approach to monoterpene indole alkaloids: total synthesis of mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam.
Article in Organic letters, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 22 papers.
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22 citing papers in PubMed, 111 citations in OpenAlex.
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- Hydrazone Activation in the Aminocatalytic Cascade Reaction for the Synthesis of Tetrahydroindolizines.Organic letters · 2024Article
- Construction of C2-indolyl-quaternary centers by branch-selective allylation: enabling concise total synthesis of the (±)-mersicarpine alkaloid.Chemical science · 2024Article
- Concise Total Synthesis of Complanadine A Enabled by Pyrrole-to-Pyridine Molecular Editing.Synthesis · 2024Article
- Iron-Mediated Photochemical Anti-Markovnikov Hydroazidation of Unactivated Olefins.Journal of the American Chemical Society · 2023Article
- Chemical Reactions of Indole Alkaloids That Enable Rapid Access to New Scaffolds for Discovery.SynOpen (2017) · 2023Article
- Total Synthesis of (±)-Aspidospermidine, (±)-Aspidofractinine, (±)-Limaspermidine, and (±)-Vincadifformine via a Cascade and Common Intermediate Strategy.The Journal of organic chemistry · 2022Article
- Recent Advances in Divergent Synthetic Strategies for Indole-Based Natural Product Libraries.Molecules (Basel, Switzerland) · 2022Review
- One-Carbon Insertion and Polarity Inversion Enabled a Pyrrole Strategy to the Total Syntheses of Pyridine-ContainingJournal of the American Chemical Society · 2021Article
- Synthesis of indole derivatives as prevalent moieties present in selected alkaloids.RSC advances · 2021Review
- Pd-Catalyzed Aerobic Oxidative Heck Cross-Coupling for the Straightforward Construction of Indole δ-Lactams.iScience · 2019Article
- Direct Intermolecular Anti-Markovnikov Hydroazidation of Unactivated Olefins.Journal of the American Chemical Society · 2019Article
- Chemistry of Bridged Lactams: Recent Developments.Molecules (Basel, Switzerland) · 2019Review
- Enantioselective palladium-catalyzed allylic alkylation reactions in the synthesis of Aspidosperma and structurally related monoterpene indole alkaloids.Natural product reports · 2018Review
- Diversity-Oriented Synthesis and Chemoinformatic Analysis of the Molecular Diversity of spFrontiers in chemistry · 2018Article
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4 authors at 2 institutions in 1 country.
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Abstract
Inspired by their potential biosynthesis, we have developed divergent total syntheses of seven monoterpene indole alkaloids including mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam, and one unnatural analogue with an unprecedented structural skeleton. The key steps involve a Witkop-Winterfeldt oxidative indole cleavage followed by transannular cyclization. The transannular cyclization product was then converted to the corresponding structural skeletons by pairing its functional groups into different reaction modes.
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