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First total syntheses of the pro-resolving lipid mediators 7(),13(),20()-Resolvin T1 and 7(),13()-Resolvin T4.促消退脂质介质7（），13（），20（）-消退素T1和7（），13（）-消退素T4的首次全合成。
Tetrahedron Lett. 2020 Feb 6;61(6). doi: 10.1016/j.tetlet.2019.151473. Epub 2019 Dec 5.
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J Intern Med. 2019 Sep;286(3):240-258. doi: 10.1111/joim.12871. Epub 2019 Jan 18.
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Resolvins in inflammation: emergence of the pro-resolving superfamily of mediators.解决素在炎症反应中的作用：促解决介质的内源性超家族的出现。
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Am J Pathol. 2018 Apr;188(4):950-966. doi: 10.1016/j.ajpath.2018.01.004.
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New maresin conjugates in tissue regeneration pathway counters leukotriene D-stimulated vascular responses.新型maresin 缀合物在组织再生途径中对抗白三烯 D 刺激的血管反应。
FASEB J. 2018 Jul;32(7):4043-4052. doi: 10.1096/fj.201701493R. Epub 2018 Feb 28.
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Mol Aspects Med. 2018 Dec;64:1-17. doi: 10.1016/j.mam.2017.08.002. Epub 2017 Sep 1.
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The novel lipid mediator PD1: An overview of the structural elucidation, synthesis, biosynthesis and bioactions.新型脂质介质PD1：结构解析、合成、生物合成及生物活性概述
Prostaglandins Other Lipid Mediat. 2017 Nov;133:103-110. doi: 10.1016/j.prostaglandins.2017.06.003. Epub 2017 Jun 7.
8
13-Series resolvins mediate the leukocyte-platelet actions of atorvastatin and pravastatin in inflammatory arthritis.13-系列消退素介导阿托伐他汀和普伐他汀在炎性关节炎中的白细胞-血小板作用。
FASEB J. 2017 Aug;31(8):3636-3648. doi: 10.1096/fj.201700268. Epub 2017 May 2.
9
Recent advances in the chemistry and biology of anti-inflammatory and specialized pro-resolving mediators biosynthesized from n-3 docosapentaenoic acid.从n-3二十二碳五烯酸生物合成的抗炎和特殊促消退介质的化学与生物学的最新进展。
Bioorg Med Chem Lett. 2017 Jun 1;27(11):2259-2266. doi: 10.1016/j.bmcl.2017.03.079. Epub 2017 Mar 31.
10
Treating inflammation and infection in the 21st century: new hints from decoding resolution mediators and mechanisms.21世纪的炎症与感染治疗：解析炎症消退介质及机制带来的新线索
FASEB J. 2017 Apr;31(4):1273-1288. doi: 10.1096/fj.201601222R. Epub 2017 Jan 13.

促消退脂质介质7（），12（），13（）-消退素T2及其13（）-差向异构体的首次全合成。

First total synthesis of the pro-resolving lipid mediator 7(),12(),13()-Resolvin T2 and its 13()-epimer.

作者信息

Rodriguez Ana R, Spur Bernd W

机构信息

Department of Cell Biology and Neuroscience, Rowan University-SOM, Stratford, NJ 08084, USA.

出版信息

Tetrahedron Lett. 2020 May 14;61(20). doi: 10.1016/j.tetlet.2020.151857. Epub 2020 Mar 19.

DOI:10.1016/j.tetlet.2020.151857
PMID:32863450
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7454203/
Abstract

The first total synthesis of the pro-resolving lipid mediator 7(),12(),13()-Resolvin T2 [7(), 12(), 13()-RvT2] and its 13()-epimer, derived from n-3 docosapentaenoic acid (n-3 DPA), are described. 7(), 12(), 13()-RvT2 and its 13()-epimer were obtained by total synthesis using a chiral pool strategy to introduce the chiral centers. C7 was generated from -(-)-1,2,4-butanetriol in both molecules and the C12 and C13 centers were generated from L-(+)-ribose and D-(-)-arabinose respectively. and -selective Wittig reactions, selective deprotections, and Dess-Martin periodinane oxidation were the key steps in the syntheses.

摘要

本文描述了源自n-3二十二碳五烯酸（n-3 DPA）的促消退脂质介质7(),12(),13()-Resolvin T2 [7(), 12(), 13()-RvT2]及其13()-差向异构体的首次全合成。7(), 12(), 13()-RvT2及其13()-差向异构体通过采用手性源策略引入手性中心的全合成方法获得。两个分子中的C7均由-(-)-1,2,4-丁三醇生成，C12和C13中心分别由L-(+)-核糖和D-(-)-阿拉伯糖生成。和-选择性维蒂希反应、选择性脱保护反应以及戴斯-马丁高碘烷氧化反应是合成中的关键步骤。