ArticleNature communications2020
Enantioselective total syntheses of (+)-stemofoline and three congeners based on a biogenetic hypothesis.
Article in Nature communications, 2020. 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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10 citing papers in PubMed, 41 citations in OpenAlex.
- Total Synthesis of (±)-Stemocurtisine via Catalytic Carbonylation.Journal of the American Chemical Society · 2026Article
- Palladium-Catalyzed Intermolecular Tandem Difunctional Carbonylation of 1,3-Enynes: Synthesis of Fluoroalkylated Butenolides.Organic letters · 2025Article
- Total syntheses of the parvistemoline alkaloids enabled by stereocontrolled Ir/Pd-catalyzed allylic alkylation.Nature communications · 2024Article
- Enantioselective and collective total synthesis of pentacyclic 19-Chemical science · 2023Article
- Catalytic enantioselective reductive alkynylation of amides enables one-pot syntheses of pyrrolidine, piperidine and indolizidine alkaloids.Nature communications · 2023Article
- Challenges and Breakthroughs in Selective Amide Activation.Angewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2022Review
- Challenges and Breakthroughs in Selective Amide Activation.Angewandte Chemie (International ed. in English) · 2022Review
- Multicatalysis protocol enables direct and versatile enantioselective reductive transformations of secondary amides.Science advances · 2022Article
- One-Pot Route from Halogenated Amides to Piperidines and Pyrrolidines.Molecules (Basel, Switzerland) · 2022Article
- Pd-catalyzed [3 + 2] cycloaddition of cyclic ketimines and trimethylenemethanes towardRSC advances · 2021Article
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The powerful insecticidal and multi-drug-resistance-reversing activities displayed by the stemofoline group of alkaloids render them promising lead structures for further development as commercial agents in agriculture and medicine. However, concise, enantioselective total syntheses of stemofoline alkaloids remain a formidable challenge due to their structural complexity. We disclose herein the enantioselective total syntheses of four stemofoline alkaloids, including (+)-stemofoline, (+)-isostemofoline, (+)-stemoburkilline, and (+)-(11S,12R)-dihydrostemofoline, in just 19 steps. Our strategy relies on a biogenetic hypothesis, which postulates that stemoburkilline and dihydrostemofolines are biogenetic precursors of stemofoline and isostemofoline. Other highlights of our approach are the use of Horner-Wadsworth-Emmons reaction to connect the two segments of the molecule, an improved protocol allowing gram-scale access to the tetracyclic cage-type core, and a Cu-catalyzed direct and versatile nucleophilic alkylation reaction on an anti-Bredt iminium ion. The synthetic techniques that we developed could also be extended to the preparation of other Stemona alkaloids.
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