ArticleNature2011
Synthesis of macrocyclic natural products by catalyst-controlled stereoselective ring-closing metathesis.
Article in Nature, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 43 papers.
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Who cites it
43 citing papers in PubMed.
- Divergent and precise alkaloid remodelling with a small suite of reactions.Nature chemistry · 2026Article
- Divergent and programmable skeletal remodeling of complex macrocycles with a small method set.Science (New York, N.Y.) · 2026Article
- Divergent access to E- or Z-trisubstituted medium-sized cycloalkenes by Pd-catalysed cycloaddition.Nature chemistry · 2025Article
- Stereocontrolled four-carbon homologation of vicinally functionalized allylic pyrrolidines to highly customized azonines bearing remote benzylic stereocenters.RSC advances · 2025Article
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- Unsaturated Macrolactones from Renewable Feedstocks: Synthesis, Ring-Opening Polymerization and Application Prospects.International journal of molecular sciences · 2025Review
- Progress in Lewis-Acid-Templated Diels-Alder Reactions.Molecules (Basel, Switzerland) · 2024Review
- (Beilstein journal of organic chemistry · 2024Article
- Chirality-matched catalyst-controlled macrocyclization reactions.Proceedings of the National Academy of Sciences of the United States of America · 2021Article
- "Canopy Catalysts" for Alkyne Metathesis: Molybdenum Alkylidyne Complexes with a Tripodal Ligand Framework.Journal of the American Chemical Society · 2020Article
- Protein-protein interaction modulators: advances, successes and remaining challenges.Biophysical reviews · 2019Review
- Recent advances in ruthenium-based olefin metathesis.Chemical Society reviews · 2018Review
- Using stereoretention for the synthesis ofChemical science · 2018Article
- A Highly Efficient Synthesis of Z-Macrocycles Using Stereoretentive, Ruthenium-Based Metathesis Catalysts.Angewandte Chemie (International ed. in English) · 2017Article
- Article
- Article
- Towards the total synthesis of keramaphidin B.Beilstein journal of organic chemistry · 2016Article
- High-value alcohols and higher-oxidation-state compounds by catalytic Z-selective cross-metathesis.Nature · 2015Article
- Catalyst-controlled stereoselective olefin metathesis as a principal strategy in multistep synthesis design: a concise route to (+)-neopeltolide.Angewandte Chemie (International ed. in English) · 2015Article
- Article
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Authors and funding
7 authors.
Funding
Abstract
Many natural products contain a C = C double bond through which various other derivatives can be prepared; the stereochemical identity of the alkene can be critical to the biological activities of such molecules. Catalytic ring-closing metathesis (RCM) is a widely used method for the synthesis of large unsaturated rings; however, cyclizations often proceed without control of alkene stereochemistry. This shortcoming is particularly costly when the cyclization reaction is performed after a long sequence of other chemical transformations. Here we outline a reliable, practical and general approach for the efficient and highly stereoselective synthesis of macrocyclic alkenes by catalytic RCM; transformations deliver up to 97% of the Z isomer owing to control induced by a tungsten-based alkylidene. Utility is demonstrated through the stereoselective preparation of epothilone C (refs 3-5) and nakadomarin A (ref. 6), the previously reported syntheses of which have been marred by late-stage, non-selective RCM. The tungsten alkylidene can be manipulated in air, delivering the products in useful yields with high stereoselectivity. As a result of efficient RCM and re-incorporation of side products into the catalytic cycle with minimal alkene isomerization, desired cyclizations proceed in preference to alternative pathways, even under relatively high substrate concentration.
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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.