ArticleAngewandte Chemie (International ed. in English)2015
Catalyst-controlled stereoselective olefin metathesis as a principal strategy in multistep synthesis design: a concise route to (+)-neopeltolide.
Article in Angewandte Chemie (International ed. in English), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed, 71 citations in OpenAlex.
- Article
- Origin and Use of Hydroxyl Group Tolerance in Cationic Molybdenum Imido Alkylidene N-Heterocyclic Carbene Catalysts.Angewandte Chemie (International ed. in English) · 2020Article
- Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules.Beilstein journal of organic chemistry · 2020Review
- Mechanism of Olefin Metathesis with Neutral and Cationic Molybdenum Imido Alkylidene N-Heterocyclic Carbene Complexes.Journal of the American Chemical Society · 2019Article
- Diastereo- and Enantioselective Access to Stereotriads through a Flexible Coupling of Substituted Aldehydes and Alkenes.Angewandte Chemie (International ed. in English) · 2019Article
- High-Performance NACS central science · 2019Article
- A tutorial review of stereoretentive olefin metathesis based on ruthenium dithiolate catalysts.Beilstein journal of organic chemistry · 2018Review
- Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.Journal of the American Chemical Society · 2016Article
- Contemporary Strategies for the Synthesis of Tetrahydropyran Derivatives: Application to Total Synthesis of Neopeltolide, a Marine Macrolide Natural Product.Marine drugs · 2016Review
- Mechanism of NHC-Catalyzed Conjugate Additions of Diboron and Borosilane Reagents to α,β-Unsaturated Carbonyl Compounds.Journal of the American Chemical Society · 2015Article
- High-value alcohols and higher-oxidation-state compounds by catalytic Z-selective cross-metathesis.Nature · 2015Article
- Strategies and Methods for the Synthesis of Anticancer Natural Product Neopeltolide and its Analogs.Current organic chemistryArticle
Corrections and comments
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Authors and funding
3 authors at 2 institutions in 1 country.
Funding
Abstract
Molybdenum-, tungsten-, and ruthenium-based complexes that control the stereochemical outcome of olefin metathesis reactions have been recently introduced. However, the complementary nature of these systems through their combined use in multistep complex molecule synthesis has not been illustrated. A concise diastereo- and enantioselective route that furnishes the anti-proliferative natural product neopeltolide is now disclosed. Catalytic transformations are employed to address every stereochemical issue. Among the featured processes are an enantioselective ring-opening/cross-metathesis promoted by a Mo monoaryloxide pyrrolide (MAP) complex and a macrocyclic ring-closing metathesis that affords a trisubstituted alkene and is catalyzed by a Mo bis(aryloxide) species. Furthermore, Z-selective cross-metathesis reactions, facilitated by Mo and Ru complexes, have been employed in the stereoselective synthesis of the acyclic dienyl moiety of the target molecule.
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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.