ArticleNature chemistry2022
E- and Z-trisubstituted macrocyclic alkenes for natural product synthesis and skeletal editing.
Article in Nature chemistry, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 25 citations in OpenAlex.
- Modular synthesis of trisubstituted olefins and 1,3-dienes from renewable alcohols via ligand-enabled nickel catalysis.Nature communications · 2026Article
- Article
- Ruthenium(II)-Catalyzed Alkenylation of Primary Arylacetamides: En Route Synthesis of Trisubstituted Alkenes.Chemistry, an Asian journal · 2026Article
- Divergent access to E- or Z-trisubstituted medium-sized cycloalkenes by Pd-catalysed cycloaddition.Nature chemistry · 2025Article
- Carbene-catalytic enantioselective synthesis of chiral macrocycles.Chemical science · 2025Review
- Exo-Selective Intramolecular (4+3) Cycloadditions to Trans-Fused Perhydroazulenes: An Asymmetric Formal Synthesis of (-)-Pseudolaric Acid B.Angewandte Chemie (International ed. in English) · 2025Article
- Palladium-catalyzed redox diversified entry to axially chiral styrenesChemical science · 2025Article
- Unsaturated Macrolactones from Renewable Feedstocks: Synthesis, Ring-Opening Polymerization and Application Prospects.International journal of molecular sciences · 2025Review
- Stereoselective Synthesis of Trisubstituted Alkenes via Copper Hydride-Catalyzed Alkyne Hydroalkylation.Journal of the American Chemical Society · 2023Article
- Catalytic Cross-Metathesis Reactions That AffordJournal of the American Chemical Society · 2023Article
- Article
Corrections and comments
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Authors and funding
7 authors at 3 institutions in 2 countries.
Funding
Abstract
Many therapeutic agents are macrocyclic trisubstituted alkenes but preparation of these structures is typically inefficient and non-selective. A possible solution would entail catalytic macrocyclic ring-closing metathesis, but these transformations require high catalyst loading, conformationally rigid precursors and are often low yielding and/or non-stereoselective. Here we introduce a ring-closing metathesis strategy for synthesis of trisubstituted macrocyclic olefins in either stereoisomeric form, regardless of the level of entropic assistance. The goal was achieved by addressing several unexpected difficulties, including complications arising from pre-ring-closing metathesis alkene isomerization. The power of the method is highlighted by two examples. The first is the near-complete reversal of substrate-controlled selectivity in the formation of a macrolactam related to an antifungal natural product. The other is a late-stage stereoselective generation of an E-trisubstituted alkene in a 24-membered ring, en route to the cytotoxic natural product dolabelide C.
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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.