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Carboxylation of Alkenes with CO2 via Photocatalytic Cleavage of C=C Double Bonds 通过光催化裂解 C=C 双键实现烯烃与二氧化碳的羧化反应
IF 2 4区 化学
Synlett Pub Date : 2024-05-14 DOI: 10.1055/s-0043-1763755
Qing-Yuan Meng, Pan-Feng Yuan
{"title":"Carboxylation of Alkenes with CO2 via Photocatalytic Cleavage of C=C Double Bonds","authors":"Qing-Yuan Meng, Pan-Feng Yuan","doi":"10.1055/s-0043-1763755","DOIUrl":"https://doi.org/10.1055/s-0043-1763755","url":null,"abstract":"The cleavage of double bonds in alkenes constitutes an integral process in converting feedstock materials into high-value synthetic intermediates. Well-known examples such as the oxidative cleavage of olefins and olefin metathesis only facilitate the synthesis of oxygen-containing compounds and the recombination of olefins. Therefore, it is appealing to extend C=C double bond cleavage to yield more abundant transformations. Herein, we report a novel photocatalytic approach for the deconstructive carboxylation of alkenes with CO2 for the synthesis of carboxylic acids in the absence of transition metals. Compared with reported carboxylations with CO2 during which carbon numbers are typically increased, we achieve the exchange of carbon dioxide with one of the carbons of the alkene double bond, thus providing carboxylic acids with unchanged carbon numbers when terminal alkenes are used.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140978188","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
One-Pot Expeditious Synthesis of Pyrazoloindolones via Base-Promoted Electrocyclization, C–N Coupling and Intramolecular Oxidative Cyclization 通过碱促进的电环化、C-N 偶联和分子内氧化环化快速合成吡唑吲哚酮类化合物
IF 2 4区 化学
Synlett Pub Date : 2024-05-14 DOI: 10.1055/a-2316-5200
Harshita Singh Korawat, Manoj Kumar Saini, Karmdeo Prajapati, Maya Shankar Singh, Ashok Kumar Basak
{"title":"One-Pot Expeditious Synthesis of Pyrazoloindolones via Base-Promoted Electrocyclization, C–N Coupling and Intramolecular Oxidative Cyclization","authors":"Harshita Singh Korawat, Manoj Kumar Saini, Karmdeo Prajapati, Maya Shankar Singh, Ashok Kumar Basak","doi":"10.1055/a-2316-5200","DOIUrl":"https://doi.org/10.1055/a-2316-5200","url":null,"abstract":"<p>Pyrazoloindolones are synthesized from <i>N</i>-tosylhydrazones in a one-pot multistep process which include base-promoted (i) electrocyclization reaction of <i>N</i>-tosylhydrazones derived from α,β-unsaturated aldehydes, (ii) aromatic nucleophilic substitution, and (iii) a domino cyclization–oxidation process under aerobic conditions.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141062305","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
Diiodine–Triethylsilane System: Formation of N-Alkylsulfonamides from Benzylic Alcohols and Sulfonamides 碘-三乙基硅烷体系：从苄醇和磺酰胺生成 N-烷基磺酰胺
IF 2 4区 化学
Synlett Pub Date : 2024-05-14 DOI: 10.1055/s-0043-1763756
Jin Jiang, Zhuo Wang, Lili Xiao
{"title":"Diiodine–Triethylsilane System: Formation of N-Alkylsulfonamides from Benzylic Alcohols and Sulfonamides","authors":"Jin Jiang, Zhuo Wang, Lili Xiao","doi":"10.1055/s-0043-1763756","DOIUrl":"https://doi.org/10.1055/s-0043-1763756","url":null,"abstract":"An operationally simple method has been developed for the synthesis of N-alkylsulfonamides from benzylic alcohols and sulfonamides in the presence of molecular iodine and triethylsilane. Various benzylic alcohols and sulfonamides were evaluated, and iodides generated in situ were shown to be the key intermediates.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140978730","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 Synthesis of Substituted Dihydropyrans by Organocatalyst-Mediated Domino Michael/enolization/acetalization Reactions 通过有机催化剂介导的多米诺迈克尔/烯醇化/缩醛化反应对取代的二氢吡喃进行对映选择性合成
IF 2 4区 化学
Synlett Pub Date : 2024-05-13 DOI: 10.1055/a-2324-8899
Yujiro Hayashi, Xiaolei Han, William Robert Hack
{"title":"Enantioselective Synthesis of Substituted Dihydropyrans by Organocatalyst-Mediated Domino Michael/enolization/acetalization Reactions","authors":"Yujiro Hayashi, Xiaolei Han, William Robert Hack","doi":"10.1055/a-2324-8899","DOIUrl":"https://doi.org/10.1055/a-2324-8899","url":null,"abstract":"A highly enantioselective synthetic method for 3,4-trans-dihydropyrans was developed by the reaction of α-acy β-aryl-substituted acrylonitrile and aldehyde catalyzed by diphenylprolinol silyl ether. This is an asymmetric domino reaction via a catalytic Michael reaction/enolization/acetalization.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140984450","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
Discovery of the Lysosome-Inhibiting Function of Acremolactone B 发现 Acremolactone B 的溶酶体抑制功能
IF 2 4区 化学
Synlett Pub Date : 2024-05-13 DOI: 10.1055/a-2325-3938
Shaonan Wang, Yali Wu, Mengyu Ba, Zhou Xu, Guoxing Gu, William G. Whittingham, Cong Liu, Ang Li, Weiwei He
{"title":"Discovery of the Lysosome-Inhibiting Function of Acremolactone B","authors":"Shaonan Wang, Yali Wu, Mengyu Ba, Zhou Xu, Guoxing Gu, William G. Whittingham, Cong Liu, Ang Li, Weiwei He","doi":"10.1055/a-2325-3938","DOIUrl":"https://doi.org/10.1055/a-2325-3938","url":null,"abstract":"Lysosome inhibitors have garnered considerable interest for their utility in lysosome biology research and potential therapeutic applications. We discovered the lysosome-inhibiting function of acremolactone B (1), a scarce azaphilone-type polyketide, leveraging our previous scalable synthesis. This compound significantly reduces lysosomal acidity and impairs the maturation of the lysosomal protease cathepsin D (CTSD) in triple-negative breast cancer cells (MDA-MB-231) and human lung cancer cells (A549). Furthermore, we found that compound 1 suppresses downstream autophagy, as revealed by monitoring autophagic flux and conducting transmission electron microscopy (TEM) analysis. This study unveils the previously unrecognized biological role of 1 and introduces a new scaffold for lysosome inhibitors.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140984362","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
Evaluation of Transiently O-6 Protected Guanosine Morpholino Nucleosides in PMO Synthesis 在 PMO 合成中对瞬时 O-6 保护的鸟苷吗啉核苷的评估
IF 2 4区 化学
Synlett Pub Date : 2024-05-08 DOI: 10.1055/a-2322-3741
Md Qasim, Atanu Ghosh, Arnab Das, Surajit Sinha
{"title":"Evaluation of Transiently O-6 Protected Guanosine Morpholino Nucleosides in PMO Synthesis","authors":"Md Qasim, Atanu Ghosh, Arnab Das, Surajit Sinha","doi":"10.1055/a-2322-3741","DOIUrl":"https://doi.org/10.1055/a-2322-3741","url":null,"abstract":"Here we present a novel strategy to synthesize O-6 protected morpholino guanosine monomers by trimethylsilylethyl group, 1-(4-azido-phenyl) ethan-1-ol and para methoxy benzyl alcohol, respectively. The introduction of this protecting group increases the solubility of the morpholino nucleoside which is crucial during PMO synthesis. HPLC analysis shows trimethylsilylethyl protected monomer gives better coupling efficiency in PMO synthesis compared to regular one. Moreover the nonpolar nature of the O-6 protected monomer facilitated the guanosine rich PMO block in solution.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140997855","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
Electrochemical Nitro Reduction to Amines Using Pinacolborane as Reducing Agents 使用频哪醇硼烷作为还原剂电化学硝基还原胺
IF 2 4区 化学
Synlett Pub Date : 2024-05-08 DOI: 10.1055/a-2322-0816
Jia-Lin Tu, Zhengjia Shen
{"title":"Electrochemical Nitro Reduction to Amines Using Pinacolborane as Reducing Agents","authors":"Jia-Lin Tu, Zhengjia Shen","doi":"10.1055/a-2322-0816","DOIUrl":"https://doi.org/10.1055/a-2322-0816","url":null,"abstract":"Nitroaromatic compounds, as hazardous industrial pollutants, have long been extensively studied for their conversion into high-value aromatic amines. However, most of these transformation reactions are confined to the use of transition metal catalysts or high-temperature conditions. Therefore, we report an electrochemical approach utilizing Pinacolborane as the reducing agent for the efficient reduction of nitroaromatic compounds. The reaction is characterized by its mild conditions, simplicity in operation, and demonstrates excellent substrate adaptability and functional group compatibility.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141000878","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 Silylative Desymmetrization of meso-Indane-1,3-diols Catalyzed by Chiral Guanidines 手性胍催化的介-茚-1,3-二醇的对映选择性硅烷化不对称反应
IF 2 4区 化学
Synlett Pub Date : 2024-05-07 DOI: 10.1055/a-2322-0904
Ayano Ui, Manaya Iwakura, Shuhei Yoshimatsu, Kenya Nakata
{"title":"Enantioselective Silylative Desymmetrization of meso-Indane-1,3-diols Catalyzed by Chiral Guanidines","authors":"Ayano Ui, Manaya Iwakura, Shuhei Yoshimatsu, Kenya Nakata","doi":"10.1055/a-2322-0904","DOIUrl":"https://doi.org/10.1055/a-2322-0904","url":null,"abstract":"Chiral guanidine-catalyzed desymmetrization of meso-indan-1,3-diols was achieved via enantioselective silylation by using chlorosilanes in good yields with high selectivity. The combination of chlorosilanes and catalysts was determined by the substituents at the C-2 position on the substrate. It was found that the fused phenyl ring on the substrate was essential for achieving high selectivity. The proposed method was found to be applicable to several types of substrates under optimized reaction conditions. Double silylative kinetic resolution with additive Horeau amplification was observed to establish high selectivity.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141002952","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 Convergent Approach to the Forskolin Skeleton 福斯科林骨架的聚合方法
IF 2 4区 化学
Synlett Pub Date : 2024-05-06 DOI: 10.1055/s-0043-1774864
Fortune O. Ononiwu, Bo Wang, Nancy I. Totah
{"title":"A Convergent Approach to the Forskolin Skeleton","authors":"Fortune O. Ononiwu, Bo Wang, Nancy I. Totah","doi":"10.1055/s-0043-1774864","DOIUrl":"https://doi.org/10.1055/s-0043-1774864","url":null,"abstract":"<p>A convergent approach to the forskolin skeleton is described. Assembly of a simplified tricyclic framework is achieved in a single step via the dihydropyrone Diels–Alder reaction. Selective manipulation of the resulting cycloadduct, in conjunction with an unusual equilibration of the C8 stereocenter, provides access to scaffolds that differ in relative stereochemistry at both the A/B and B/C ring junctions.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140885179","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
Bismuth Triflate Catalyzed Intermolecular Cyclization of Thiophenols with Allylic Alcohols 三氟化铋催化噻吩醇与烯丙基醇的分子间环化反应
IF 2 4区 化学
Synlett Pub Date : 2024-05-06 DOI: 10.1055/a-2312-0631
Maki Minakawa, Taichi Inaba, Shoki Oikawa
{"title":"Bismuth Triflate Catalyzed Intermolecular Cyclization of Thiophenols with Allylic Alcohols","authors":"Maki Minakawa, Taichi Inaba, Shoki Oikawa","doi":"10.1055/a-2312-0631","DOIUrl":"https://doi.org/10.1055/a-2312-0631","url":null,"abstract":"<p>The catalytic intermolecular cyclization of thiophenols with allylic alcohols in the presence of bismuth triflate afforded the corresponding thiochromane derivatives in a one-pot reaction. The Bi(OTf)<sub>3</sub>-catalyzed reaction was also applied to the intermolecular cyclization of diaryl disulfides with 3-methylbut-2-en-1-ol to produce the corresponding thiochromanes.</p>","PeriodicalId":22319,"journal":{"name":"Synlett","volume":null,"pages":null},"PeriodicalIF":2.0,"publicationDate":"2024-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140885178","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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