ArticleNature chemistry2009
Total synthesis and study of 6-deoxyerythronolide B by late-stage C-H oxidation.
Article in Nature chemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 50 papers.
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50 citing papers in PubMed.
- Chiral Anthranyl Bis-sulfoxides with Modular Chiroptical Properties Controlled by an Ionic Stimulus.ACS omega · 2026Article
- Transition Metal-Catalyzed Direct C(spChemical reviews · 2026Review
- Enantioselective C-H functionalization: logic and applications in the total synthesis of natural products.Chemical science · 2026Review
- Substrate Trapping in Polyketide Synthase Thioesterase Domains: Structural Basis for Macrolactone Formation.ACS catalysis · 2024Article
- General Regio- and Diastereoselective Allylic C-H Oxygenation of Internal Alkenes.Journal of the American Chemical Society · 2024Article
- A preparative small-molecule mimic of liver CYP450 enzymes in the aliphatic C-H oxidation of carbocyclicProceedings of the National Academy of Sciences of the United States of America · 2023Article
- Macrolactonization of methyl 15-hydroxypentadecanoate to cyclopentadecanolide using KF-La/γ-AlRoyal Society open science · 2022Article
- Late-Stage Chemoenzymatic Installation of Hydroxy-Bearing Allyl Moiety on the Indole Ring of Tryptophan-Containing Peptides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Site-Selective Copper-Catalyzed Azidation of Benzylic C-H Bonds.Journal of the American Chemical Society · 2020Article
- Site-selective, catalytic, and diastereoselective spRSC advances · 2020Article
- Article
- Chemoselective Tertiary C-H Hydroxylation for Late-Stage Functionalization with Mn(PDP)/Chloroacetic Acid Catalysis.Advanced synthesis & catalysis · 2020Article
- Feedstock Reagents in Metal-Catalyzed Carbonyl Reductive Coupling: Minimizing Preactivation for Efficiency in Target-Oriented Synthesis.Angewandte Chemie (International ed. in English) · 2019Review
- Aerobic Acyloxylation of Allylic C-H Bonds Initiated by a PdChemSusChem · 2019Article
- Operando Spectroscopic and Kinetic Characterization of Aerobic Allylic C-H Acetoxylation Catalyzed by Pd(OAc)Journal of the American Chemical Society · 2019Article
- Aliphatic C-H Oxidations for Late-Stage Functionalization.Journal of the American Chemical Society · 2018Review
- C-H to C-N Cross-Coupling of Sulfonamides with Olefins.Journal of the American Chemical Society · 2018Article
- A unified photoredox-catalysis strategy for C(spChemical science · 2017Article
- The Therapeutic Potential of Migrastatin-Core Analogs for the Treatment of Metastatic Cancer.Molecules (Basel, Switzerland) · 2017Review
- 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
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Abstract
Among the frontier challenges in chemistry in the twenty-first century are the interconnected goals of increasing synthetic efficiency and diversity in the construction of complex molecules. Oxidation reactions of C-H bonds, particularly when applied at late stages of complex molecule syntheses, hold special promise for achieving both these goals. Here we report a late-stage C-H oxidation strategy in the total synthesis of 6-deoxyerythronolide B (6-dEB), the aglycone precursor to the erythromycin antibiotics. An advanced intermediate is cyclized to give the 14-membered macrocyclic core of 6-dEB using a late-stage (step 19 of 22) C-H oxidative macrolactonization reaction that proceeds with high regio-, chemo- and diastereoselectivity (>40:1). A chelate-controlled model for macrolactonization predicted the stereochemical outcome of C-O bond formation and guided the discovery of conditions for synthesizing the first diastereomeric 13-epi-6-dEB precursor. Overall, this C-H oxidation strategy affords a highly efficient and stereochemically versatile synthesis of the erythromycin core.
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