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Functionalization of Lewis base (LB) in LB–BR3 adducts LB - br3加合物中路易斯碱（LB）的功能化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-11-26 DOI: 10.1016/j.tetlet.2024.155372
Pan Xu , Xuenian Chen , Zhenxing Liu
{"title":"Functionalization of Lewis base (LB) in LB–BR3 adducts","authors":"Pan Xu ,&nbsp;Xuenian Chen ,&nbsp;Zhenxing Liu","doi":"10.1016/j.tetlet.2024.155372","DOIUrl":"10.1016/j.tetlet.2024.155372","url":null,"abstract":"<div><div>Whenever a Lewis base borane is formed, the Lewis base will affect the properties of borane. The opposite is similarly true, that borane will affect the properties of Lewis base. The current development of Lewis base borane adducts mainly focuses on the borane part. Less chemistry is known about the Lewis base part. Herein, we selected examples to highlight the functionalization of the Lewis base of LB–BR<sub>3</sub> adducts. Parts I and II focus on showing how boranes promote coupling, substitution, and reduction reactions of amine and phosphine in the corresponding borane adducts, as well as borane’s control of the regioselectivity and stereoselectivity of amine-boron and phosphine-borane analogs. Part III focuses on the effect of boranes on the chemistry of Lewis bases containing carbon, oxygen, and sulfur.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155372"},"PeriodicalIF":1.5,"publicationDate":"2024-11-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142744054","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of 1,4-benzodioxepinones via electrochemical oxyselenenylation of 2-O-tethered alkenyl benzoic acid and diselenides 2- o系链烯基苯甲酸和二硒烯酸的电化学氧硒化合成1,4-苯并二苯二酮类化合物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-11-24 DOI: 10.1016/j.tetlet.2024.155389
Junsheng Hou , Bingxin You , Ruiqi Lv , Xinxin Zhang , Hao Zhang , Qiang Liu
{"title":"Synthesis of 1,4-benzodioxepinones via electrochemical oxyselenenylation of 2-O-tethered alkenyl benzoic acid and diselenides","authors":"Junsheng Hou ,&nbsp;Bingxin You ,&nbsp;Ruiqi Lv ,&nbsp;Xinxin Zhang ,&nbsp;Hao Zhang ,&nbsp;Qiang Liu","doi":"10.1016/j.tetlet.2024.155389","DOIUrl":"10.1016/j.tetlet.2024.155389","url":null,"abstract":"<div><div>An efficient methodology for the synthesis of seven-membered benzodioxepinones has been developed via electrochemical oxyselenenylation of 2-<em>O</em>-tethered alkenyl benzoic acid and diselenides under an external oxidant-free condition at room temperature. The experimental evidence supports this transformation through a radical mechanism.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155389"},"PeriodicalIF":1.5,"publicationDate":"2024-11-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142744052","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Convenient synthesis of O-alkylated/N-acylated polyhydroxyazepane based compounds for modulating MD-2-TLR4 complex formation 方便合成 O-烷基化/N-酰基化多羟基氮杂环庚烷基化合物，用于调节 MD-2-TLR4 复合物的形成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-11-23 DOI: 10.1016/j.tetlet.2024.155388
Sumit , Sudipta Nandi , Indrapal Singh Aidhen
{"title":"Convenient synthesis of O-alkylated/N-acylated polyhydroxyazepane based compounds for modulating MD-2-TLR4 complex formation","authors":"Sumit ,&nbsp;Sudipta Nandi ,&nbsp;Indrapal Singh Aidhen","doi":"10.1016/j.tetlet.2024.155388","DOIUrl":"10.1016/j.tetlet.2024.155388","url":null,"abstract":"<div><div>Toll-like receptor 4 (TLR4) is a critical component of the innate immune system, recognizing lipopolysaccharide (LPS) from Gram-negative bacteria and triggering immune responses. The activation of TLR4 involves several key steps, including interactions with LPS-binding protein (LBP), CD14, and myeloid differentiation protein 2 (MD-2), culminating in the formation of the (LPS.MD-2 TLR4)<sub>2</sub> complex. Structural insights show that LPS acyl chains insert into the hydrophobic pocket of MD-2, driving TLR4 activation. Inspired by this understanding, numerous natural and synthetic compounds have been developed to inhibit TLR4 by targeting the MD-2/TLR4 complex. Eritoran <strong>1</strong>, is one such illustration. The conformational flexibility of azepane architecture inspired us to visualize <em>O</em>-alkylated/<em>N</em>-acylated polyhydroxyazepane-based compounds toward this objective. The docking studies and molecular simulation studies supported the rationale. Synthesis of <em>O</em>-alkylated/<em>N</em>-acylated polyhydroxyazepane-based compounds <strong>2</strong>-<strong>4</strong> (<strong>a</strong>-<strong>h</strong>) through a key building block is described herein.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155388"},"PeriodicalIF":1.5,"publicationDate":"2024-11-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142719961","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
A practical synthesis of Cbz protected (1R,2R) and (1S,2S) 2-hydroxy-cyclobutylamines Cbz保护的（1R,2R）和（1S,2S） 2-羟基环丁胺的实际合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-11-23 DOI: 10.1016/j.tetlet.2024.155391
Can Jin, Yilin Wang, Xiangsheng Xu, Xiaoqing Li
{"title":"A practical synthesis of Cbz protected (1R,2R) and (1S,2S) 2-hydroxy-cyclobutylamines","authors":"Can Jin,&nbsp;Yilin Wang,&nbsp;Xiangsheng Xu,&nbsp;Xiaoqing Li","doi":"10.1016/j.tetlet.2024.155391","DOIUrl":"10.1016/j.tetlet.2024.155391","url":null,"abstract":"<div><div><em>(1R,2R)</em> and <em>(1S,2S)</em> 2-hydroxy-cyclobutylamines are important substructures in a range of bio-active molecules and pharmaceutical candidates. In view of the potential safety issues and the low reaction efficiency associated with the earlier published synthetic process, which relies on Curtius rearrangement for the synthesis of 2-amino-cyclobutanone intermediate, a more practical and efficient process to prepare <em>(1R,2R)</em> and <em>(1S,2S)</em> 2-hydroxy-cyclobutylamines using readily available <em>N-</em>Cbz-2-amino-cyclobutanone was developed. Cbz protected <em>(1R,2R)</em> 2-hydroxy-cyclobutylamine could be synthesized in 14 % yield over 5 steps.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155391"},"PeriodicalIF":1.5,"publicationDate":"2024-11-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142744049","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Efficient synthesis of highly substituted benzoselenazole derivatives through the one-pot, multi-step Ullmann coupling reaction 一锅多步乌尔曼偶联反应高效合成高取代苯并硒唑衍生物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-11-23 DOI: 10.1016/j.tetlet.2024.155387
Manijeh Nematpour
{"title":"Efficient synthesis of highly substituted benzoselenazole derivatives through the one-pot, multi-step Ullmann coupling reaction","authors":"Manijeh Nematpour","doi":"10.1016/j.tetlet.2024.155387","DOIUrl":"10.1016/j.tetlet.2024.155387","url":null,"abstract":"<div><div>In this research, the simple and efficient method for the synthesis of highly substituted benzoselenazole derivatives using the one-pot, multi-step Ullman coupling reaction of acyl isoselenocyanate-nitro compounds adducts and dihalobenzene in the vicinity of K<sub>2</sub>CO<sub>3</sub> as a base, copper iodide, at room temperature, and in MeCN solvent has been done successfully. The use of simple and available raw materials, mild copper catalytic reaction conditions, easy purification with the help of solvent, and finally the synthesis of 16 new compounds from the benzoselenazoles family are notable features of this protocol.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155387"},"PeriodicalIF":1.5,"publicationDate":"2024-11-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142744050","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Biomimetic oxidation of tetracycline and derivatives at C11a 四环素及其 C11a 衍生物的生物模拟氧化作用
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-11-22 DOI: 10.1016/j.tetlet.2024.155366
He Wu, Yong Wang, Guangguang Yang, Karuppu Selvaraj, Gang Chen
{"title":"Biomimetic oxidation of tetracycline and derivatives at C11a","authors":"He Wu,&nbsp;Yong Wang,&nbsp;Guangguang Yang,&nbsp;Karuppu Selvaraj,&nbsp;Gang Chen","doi":"10.1016/j.tetlet.2024.155366","DOIUrl":"10.1016/j.tetlet.2024.155366","url":null,"abstract":"<div><div>Tetracycline destructases (TDases), a type of TC-inactivating enzymes, inactivate all known TC antibiotics by C11a oxidation, which is considered as a clinical threat. To provide more information on this enzymatic inactivation and oxygenated TCs, we report here a chemical oxidation of Tetracycline and its derivatives at the C11a position using <em>m</em>-CPBA with additives via biomimetic pathways. The structures of the oxygen-containing TCs (<strong>2h, 2i</strong>) were confirmed by X-ray analysis, and further transformations were performed with oxygen-containing TCs (<strong>2e</strong>, <strong>2i</strong>).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155366"},"PeriodicalIF":1.5,"publicationDate":"2024-11-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142702929","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis of 2,4,5-vinylic-trisubstituted oxazoles via a Palladium-catalyzed cascade coupling reaction 通过钯催化级联偶联反应合成 2,4,5-乙烯基三取代噁唑
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-11-21 DOI: 10.1016/j.tetlet.2024.155373
Jun Ma , Huali Wang , Qingyu Meng , Haoyue Wang , Fangyi Li , Zheng Li
{"title":"Synthesis of 2,4,5-vinylic-trisubstituted oxazoles via a Palladium-catalyzed cascade coupling reaction","authors":"Jun Ma ,&nbsp;Huali Wang ,&nbsp;Qingyu Meng ,&nbsp;Haoyue Wang ,&nbsp;Fangyi Li ,&nbsp;Zheng Li","doi":"10.1016/j.tetlet.2024.155373","DOIUrl":"10.1016/j.tetlet.2024.155373","url":null,"abstract":"<div><div>A novel one-step synthesis of valuable 2,4,5-vinylic-trisubstituted oxazoles is described. This reaction, utilizing readily available β,β-dibrominated secondary enamides and terminal alkenes as starting materials, occurs via a ligand-free Palladium-catalyzed cascade intramolecular C<img>O coupling/intermolecular Heck reaction.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"153 ","pages":"Article 155373"},"PeriodicalIF":1.5,"publicationDate":"2024-11-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142699332","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
The first enantioselective total synthesis of the eremophilane-type sesquiterpenoid (−)-peniroqueforin C 首次对映选择性全合成乙内酰脲类倍半萜化合物 (-)-peniroqueforin C
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-11-20 DOI: 10.1016/j.tetlet.2024.155386
Sudhir R. Ingale , Ramavath Vinodkumar , Ravindar Kontham
{"title":"The first enantioselective total synthesis of the eremophilane-type sesquiterpenoid (−)-peniroqueforin C","authors":"Sudhir R. Ingale ,&nbsp;Ramavath Vinodkumar ,&nbsp;Ravindar Kontham","doi":"10.1016/j.tetlet.2024.155386","DOIUrl":"10.1016/j.tetlet.2024.155386","url":null,"abstract":"<div><div>Herein, we report the first stereoselective total synthesis of the eremophilane-type sesquiterpenoid (−)-peniroqueforin C using a chiral-pool strategy. This synthetic route features the use of readily available (<em>S</em>)-(+)-carvone as a chiral building block, Robinson annulation to construct the decalin system, substrate-controlled stereoselective methylation, single-step annulative construction of a tricyclic <em>γ</em>-ylidene-butenolide with concomitant alkene transposition, and direct lactone-to-lactam conversion as key transformations.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155386"},"PeriodicalIF":1.5,"publicationDate":"2024-11-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142702926","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Palladium-catalyzed cycloisomerization of thiocarbamates with consecutive formation of quaternary carbon and sulfide 钯催化硫代氨基甲酸酯的环异构化，并连续形成季碳和硫化物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-11-19 DOI: 10.1016/j.tetlet.2024.155384
Hyu Kumazawa, Masahisa Nakada
{"title":"Palladium-catalyzed cycloisomerization of thiocarbamates with consecutive formation of quaternary carbon and sulfide","authors":"Hyu Kumazawa,&nbsp;Masahisa Nakada","doi":"10.1016/j.tetlet.2024.155384","DOIUrl":"10.1016/j.tetlet.2024.155384","url":null,"abstract":"<div><div>The Pd-catalyzed cycloisomerization of thiocarbamates with consecutive formation of a quaternary carbon and a sulfide is described. This Pd-catalyzed cascade reaction occurred with both alkylthiocarbamates and arylthiocarbamates, and arylthiocarbamates reacted faster than alkylthiocarbamates. The Pd-catalyzed cycloisomerization can be applied to phenylene- and alkylene-tethered substrates, and thiocarbamate was found to be less reactive than carbamimidothioate. The Pd-catalyzed cycloisomerization can be used to form bridged rings and is expected to be useful for ring construction of nitrogen-containing polycyclic natural products.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155384"},"PeriodicalIF":1.5,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142702930","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Enantioselective gold/enzyme dual catalysis 对映选择性金/酶双催化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2024-11-19 DOI: 10.1016/j.tetlet.2024.155382
Amit Patwa, Chayanika Pegu, Bidisha Paroi, Nitin T. Patil
{"title":"Enantioselective gold/enzyme dual catalysis","authors":"Amit Patwa,&nbsp;Chayanika Pegu,&nbsp;Bidisha Paroi,&nbsp;Nitin T. Patil","doi":"10.1016/j.tetlet.2024.155382","DOIUrl":"10.1016/j.tetlet.2024.155382","url":null,"abstract":"<div><div>Over the decades, enantioselective metal/enzyme dual catalysis has emerged as a dynamic area of research in asymmetric synthesis. By leveraging the unique reactivities of metal/enzyme dual catalysis, numerous transformations have been developed, primarily relying on metals such as Pd, Ru, Ir, Fe and Au. Among all transition metals, gold stands out as the catalyst of choice due to its soft <em>π</em>-acidic nature. The <em>π</em>-activation reactivities of gold catalysts have been strategically integrated with enzyme catalysis, thereby leading to highly enantioselective transformations that are unattainable <em>via</em> a single catalyst alone. This review endeavors to provide an overview of the advancements in enantioselective gold/enzyme dual catalysis.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"154 ","pages":"Article 155382"},"PeriodicalIF":1.5,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142702928","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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