ArticleThe Journal of organic chemistry2021
Stereoselective Synthesis and Structural Confirmation of the Specialized Pro-Resolving Mediator Resolvin E4.
Article in The Journal of organic chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- FeClChemistryOpen · 2026Article
- Advances in the role of specialized pro-resolving mediators in periodontitis.Frontiers in immunology · 2026Review
- Proresolving Lipid Mediators in the Respiratory System.Annual review of physiology · 2025Review
- 15-epi-lipoxin AFASEB journal : official publication of the Federation of American Societies for Experimental Biology · 2024Article
- Biology and Total Synthesis of n-3 Docosapentaenoic Acid-Derived Specialized Pro-Resolving Mediators.Molecules (Basel, Switzerland) · 2024Review
- Metabolization of Resolvin E4 by ω-Oxidation in Human Neutrophils: Synthesis and Biological Evaluation of 20-Hydroxy-Resolvin E4 (20-OH-RvE4).ACS pharmacology & translational science · 2023Article
- Stereoselective Synthesis, Pro-resolution, and Anti-inflammatory Actions of RvD5Journal of natural products · 2023Article
- Specialized Pro-Resolving Lipid Mediators: Endogenous Roles and Pharmacological Activities in Infections.Molecules (Basel, Switzerland) · 2023Review
- Resolvins and cysteinyl-containing pro-resolving mediators activate resolution of infectious inflammation and tissue regeneration.Prostaglandins & other lipid mediators · 2023Review
- A Modular Strategy for the Synthesis of Dothideopyrones E and F, Secondary Metabolites from an Endolichenic Fungus.Journal of natural products · 2023Article
- Possibility of averting cytokine storm in SARS-COV 2 patients using specialized pro-resolving lipid mediators.Biochemical pharmacology · 2023Review
- First stereoselective total synthesis of 4(RSC advances · 2022Article
- Stereoselective Synthesis, Configurational Assignment and Biological Evaluations of the Lipid Mediator RvD2Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- E-series resolvin metabolome, biosynthesis and critical role of stereochemistry of specialized pro-resolving mediators (SPMs) in inflammation-resolution: Preparing SPMs for long COVID-19, human clinical trials, and targeted precision nutrition.Seminars in immunology · 2022Review
- Formation, Signaling and Occurrence of Specialized Pro-Resolving Lipid Mediators-What is the Evidence so far?Frontiers in pharmacology · 2022Review
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6 authors.
Funding
Abstract
Herein, we report the stereoselective and convergent synthesis of resolvin E4, a newly identified specialized pro-resolving mediator. This synthesis proves the absolute configuration and exact olefin geometry. Key elements of the successful strategy include a highly stereoselective MacMillan organocatalytic oxyamination, a Midland Alpine borane reduction, and the use of a 1,4-pentadiyne unit as a linchpin building block. The application of reaction telescoping in several of the synthetic transformations enabled the preparation of the resolvin E4 methyl ester in 10% yield over 10 steps (longest linear sequence). The physical property (UV-Vis and LC-MS/MS) data of synthetic resolvin E4 matched those obtained from biologically produced material.
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