ArticleJournal of the American Chemical Society2016
Enantioselective Alcohol C-H Functionalization for Polyketide Construction: Unlocking Redox-Economy and Site-Selectivity for Ideal Chemical Synthesis.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 56 papers.
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Who cites it
56 citing papers in PubMed.
- Bioinspired total synthesis of (+)-pleuromutilin.Nature communications · 2026Article
- Enantioselective Carbonyl Crotylation of Alcohol Proelectrophiles via Ruthenium-Catalyzed Hydrogen Autotransfer: Innovation Inspired by Polyketide Total Synthesis.ACS catalysis · 2026Article
- Total Synthesis ofJournal of the American Chemical Society · 2026Article
- Enantioselective Butadiene-Mediated Aldehyde Crotylation of Alcohol Proelectrophiles: RuHCl(CO)(PPhOrganic letters · 2026Article
- General Modular and Convergent Approach to Diversely Functionalized Allylic Systems.Journal of the American Chemical Society · 2025Article
- Enantioselective β-C(spJournal of the American Chemical Society · 2025Article
- Formal Synthesis of Fostriecin via Asymmetric Alcohol-Mediated Carbonyl Allylation.Organic letters · 2025Article
- Catalytic Enantioselective C-C Coupling of Alcohols for Polyketide Total Synthesis beyond Chiral Auxiliaries and Premetalated Reagents.Chemical reviews · 2024Review
- Total Synthesis of the Phenylnaphthacenoid Type II Polyketide Antibiotic Formicamycin H via Regioselective Ruthenium-Catalyzed Hydrogen Auto-Transfer [4 + 2] Cycloaddition.Journal of the American Chemical Society · 2024Article
- General Regio- and Diastereoselective Allylic C-H Oxygenation of Internal Alkenes.Journal of the American Chemical Society · 2024Article
- Total Synthesis of the Allenic Macrolide (+)-Archangiumide.Journal of the American Chemical Society · 2024Article
- Total syntheses of Tetrodotoxin and 9-epiTetrodotoxin.Nature communications · 2024Article
- Iridium-Catalysed Transfer Hydrogenation of 1,8-Naphthyridine with Indoline: Access to Functionalized N-Heteroarenes.Molecules (Basel, Switzerland) · 2023Article
- Asymmetric Syntheses of (Journal of the American Chemical Society · 2023Article
- Enantioselective Transfer Hydrogenative Cycloaddition Unlocks the Total Synthesis of SF2446 B3: An Aglycone of Arenimycin and SF2446 Type II Polyketide Antibiotics.Journal of the American Chemical Society · 2023Article
- Article
- Allyl Alcohol as an Acrolein Equivalent in Enantioselective C-C Coupling: Total Synthesis of Amphidinolides R, J, and S.Journal of the American Chemical Society · 2023Article
- Asymmetric Ruthenium-Catalyzed Carbonyl Allylations by Gaseous Allene via Hydrogen Auto-Transfer: 1° vs 2° Alcohol Dehydrogenation for Streamlined Polyketide Construction.ACS catalysis · 2023Article
- Counting steps.Nature synthesis · 2023Article
- Ruthenium-Catalyzed Butadiene-Mediated Crotylation and Oxazaborolidine-Catalyzed Vinylogous Mukaiyama Aldol Reaction for The Synthesis of C1-C19 and C23-C35 of Neaumycin B.Angewandte Chemie (International ed. in English) · 2022Article
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3 authors.
Funding
Abstract
The development and application of stereoselective and site-selective catalytic methods that directly convert lower alcohols to higher alcohols are described. These processes merge the characteristics of transfer hydrogenation and carbonyl addition, exploiting alcohols and π-unsaturated reactants as redox pairs, which upon hydrogen transfer generate transient carbonyl-organometal pairs en route to products of C-C coupling. Unlike classical carbonyl additions, stoichiometric organometallic reagents and discrete alcohol-to-carbonyl redox reactions are not required. Additionally, due to a kinetic preference for primary alcohol dehydrogenation, the site-selective modification of glycols and higher polyols is possible, streamlining or eliminating use of protecting groups. The total syntheses of several iconic type I polyketide natural products were undertaken using these methods. In each case, the target compounds were prepared in significantly fewer steps than previously achieved.
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