ArticleJournal of the American Chemical Society2014
Catalytic Z-selective cross-metathesis in complex molecule synthesis: a convergent stereoselective route to disorazole C1.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Anticancer Compounds from Myxobacteria: Current Scenario and Future Perspectives.Anti-cancer agents in medicinal chemistry · 2026Review
- Highly Stereo- and Enantioselective Syntheses of δ-Alkyl-Substituted (Organic letters · 2025Article
- Cyclization by Intramolecular Suzuki-Miyaura Cross-Coupling-A Review.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Review
- Cobalt catalyzed practical hydroboration of terminal alkynes with time-dependent stereoselectivity.Nature communications · 2024Article
- Synthesis and Biological Evaluation of C(13)/C(13')-Bis(desmethyl)disorazole Z.Angewandte Chemie (International ed. in English) · 2023Article
- Catalytic enantioselective synthesis of macrodiolides and their application in chiral recognition.Chemical science · 2020Article
- A Catalytic Approach for Enantioselective Synthesis of Homoallylic Alcohols Bearing aJournal of the American Chemical Society · 2020Article
- Origin and Use of Hydroxyl Group Tolerance in Cationic Molybdenum Imido Alkylidene N-Heterocyclic Carbene Catalysts.Angewandte Chemie (International ed. in English) · 2020Article
- Mechanism of Olefin Metathesis with Neutral and Cationic Molybdenum Imido Alkylidene N-Heterocyclic Carbene Complexes.Journal of the American Chemical Society · 2019Article
- Synthesis of 2,6-Hexa-tert-butylterphenyl Derivatives, 2,6-(2,4,6-t-BuOrganic letters · 2017Article
- Article
- Syntheses of Molybdenum Adamantylimido andOrganometallics · 2017Article
- Synthesis of Linear (Z)-α,β-Unsaturated Esters by Catalytic Cross-Metathesis. The Influence of Acetonitrile.Angewandte Chemie (International ed. in English) · 2016Article
- Article
- Self-Assembly of Disorazole CAngewandte Chemie (Weinheim an der Bergstrasse, Germany) · 2015Article
- Self-Assembly of Disorazole C1 through a One-Pot Alkyne Metathesis Homodimerization Strategy.Angewandte Chemie (International ed. in English) · 2015Article
- Preparation of macrocyclic Z-enoates and (E,Z)- or (Z,E)-dienoates through catalytic stereoselective ring-closing metathesis.Journal of the American Chemical Society · 2014Article
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Authors and funding
5 authors.
Funding
Abstract
A convergent diastereo- and enantioselective total synthesis of anticancer and antifungal macrocyclic natural product disorazole C1 is reported. The central feature of the successful route is the application of catalytic Z-selective cross-metathesis (CM). Specifically, we illustrate that catalyst-controlled stereoselective CM can be performed to afford structurally complex Z-alkenyl-B(pin) as well as Z-alkenyl iodide compounds reliably, efficiently, and with high selectivity (pin = pinacolato). The resulting intermediates are then joined in a single-step operation through catalytic inter- and intramolecular cross-coupling to furnish the desired 30-membered ring macrocycle containing the critical (Z,Z,E)-triene moieties.
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Registered trials
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