ArticleJournal of the American Chemical Society2013
Total synthesis of 6-deoxyerythronolide B via C-C bond-forming transfer hydrogenation.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
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Who cites it
29 citing papers in PubMed.
- Enantioselective Carbonyl Crotylation of Alcohol Proelectrophiles via Ruthenium-Catalyzed Hydrogen Autotransfer: Innovation Inspired by Polyketide Total Synthesis.ACS catalysis · 2026Article
- Distinct Acyl Carrier Protein Docking Sites Help Mediate the Opposite Stereoselectivities of A- and B-type Modular Polyketide Synthase Ketoreductases.Biochemistry · 2025Article
- Catalytic Enantioselective C-C Coupling of Alcohols for Polyketide Total Synthesis beyond Chiral Auxiliaries and Premetalated Reagents.Chemical reviews · 2024Review
- Article
- Stereo- and Site-Selective Crotylation of Alcohol Proelectrophiles via Ruthenium-Catalyzed Hydrogen Auto-Transfer Mediated by Methylallene and Butadiene.Angewandte Chemie (International ed. in English) · 2022Article
- Historical perspective on ruthenium-catalyzed hydrogen transfer and survey of enantioselective hydrogen auto-transfer processes for the conversion of lower alcohols to higher alcohols.Chemical science · 2022Review
- Robust and Self-Cleaning Electrochemical Production of Periodate.ChemSusChem · 2022Article
- Total Synthesis of the Spliceosome Modulator Pladienolide B via Asymmetric Alcohol-Mediated syn- and anti-Diastereoselective Carbonyl Crotylation.Angewandte Chemie (International ed. in English) · 2021Article
- From Hydrogenation to Transfer Hydrogenation to Hydrogen Auto-Transfer in Enantioselective Metal-Catalyzed Carbonyl Reductive Coupling: Past, Present, and Future.ACS catalysis · 2021Article
- The "Green" Electrochemical Synthesis of Periodate.Angewandte Chemie (International ed. in English) · 2020Article
- Enantioselective Iridium-Catalyzed Allylation of Acetylenic Ketones via 2-Propanol-Mediated Reductive Coupling of Allyl Acetate: C14-C23 of Pladienolide D.Angewandte Chemie (International ed. in English) · 2019Article
- Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.Angewandte Chemie (International ed. in English) · 2019Review
- Total Synthesis of Clavosolide A via Asymmetric Alcohol-Mediated Carbonyl Allylation: Beyond Protecting Groups or Chiral Auxiliaries in Polyketide Construction.Angewandte Chemie (International ed. in English) · 2019Article
- Intermolecular Metal-Catalyzed Reductive Coupling of Dienes, Allenes, and Enynes with Carbonyl Compounds and Imines.Chemical reviews · 2018Review
- Synthesis of Benzyl Amines via Copper-Catalyzed Enantioselective Aza-Friedel-Crafts Addition of Phenols to N-Sulfonyl Aldimines.Organic letters · 2018Article
- Toward Generalization of Iterative Small Molecule Synthesis.Nature reviews. Chemistry · 2018Article
- Total Synthesis of Swinholide A: An Exposition in Hydrogen-Mediated C-C Bond Formation.Journal of the American Chemical Society · 2016Article
- 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
- Asymmetric Iridium-Catalyzed C-C Coupling of Chiral Diols via Site-Selective Redox-Triggered Carbonyl Addition.Topics in current chemistry · 2016Review
- Application of a High-Throughput Enantiomeric Excess Optical Assay Involving a Dynamic Covalent Assembly: Parallel Asymmetric Allylation andChemical science · 2015Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
The 14-membered macrolide 6-deoxyerythronolide B is prepared in 14 steps (longest linear sequence) and 20 total steps. Two different methods for alcohol CH-crotylation via transfer hydrogenation are deployed for the first time in target-oriented synthesis. Enyne metathesis is used to form the 14-membered ring. The present approach represents the most concise construction of any erythronolide reported, to date.
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