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Anti-Inflammatory α-Pyrone Polyethers Generated by Interrupting the Enolized 1,3-Diketone Formation in the Polyketide Synthases of Calcium-Ionophore Ionomycin.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-18 DOI: 10.1021/acs.orglett.4c04711
Mengjia Li, Jing Xu, Haixia Zang, Wen-Rui Peng, Li-Li Hong, Chang Xu, Wanlu Li, Wei-Hua Jiao, Hou-Wen Lin, Yongjun Zhou
{"title":"Anti-Inflammatory α-Pyrone Polyethers Generated by Interrupting the Enolized 1,3-Diketone Formation in the Polyketide Synthases of Calcium-Ionophore Ionomycin.","authors":"Mengjia Li, Jing Xu, Haixia Zang, Wen-Rui Peng, Li-Li Hong, Chang Xu, Wanlu Li, Wei-Hua Jiao, Hou-Wen Lin, Yongjun Zhou","doi":"10.1021/acs.orglett.4c04711","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04711","url":null,"abstract":"<p><p>Carboxyl polyethers from <i>Actinomycetes</i> have diverse bioactivities, being biosynthesized by type-I polyketide synthetases. Of them, ionomycin, the commercial calcium ionophore, bears a unique enolized 1,3-diketone moiety. Herein, mutagenetic analysis of ionomycin biosynthesis revealed a rare dehydrogenase gene <i>ino</i>J putatively involved in enol moiety formation. Interruption of the enolized 1,3-diketone formation by inactivating a ketoreductase domain yielded the first natural polyether with an α-pyrone ring, which was demonstrated with significant anti-inflammatory activity in a mouse colitis model.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143447437","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 Synthesis of Tridentate Bicyclocalixarene Cage Molecules.
IF 4.9 1区 化学
Organic Letters Pub Date : 2025-02-18 DOI: 10.1021/acs.orglett.5c00037
Na Lin, Ruize Xie, Haoqing Jia, Yin Chen
{"title":"One-Pot Synthesis of Tridentate Bicyclocalixarene Cage Molecules.","authors":"Na Lin, Ruize Xie, Haoqing Jia, Yin Chen","doi":"10.1021/acs.orglett.5c00037","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00037","url":null,"abstract":"<p><p>Efficient one-pot synthesis of tridentate bicyclocalixarenes was developed by condensing phloroglucinol with dechlorinated pyrimidine or triazine with a yield up to 58%. These cage-like molecules adopt a symmetric three-blade propeller structure with different terminal function groups and arm spans ranging from 7.5 to 15.8 Å. Due to the 1,3-alternate configuration of intermediate heterocalixarenes, the cage molecules can be prepared only with benzene rings as the upper and lower caps. They will be an ideal scaffold for the preparation of ultrathin two-dimensional materials.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":" ","pages":""},"PeriodicalIF":4.9,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143447443","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Preparation of 2-Heteroaryl-indolin-3-ones by Acid-Mediated Intramolecular Cyclization in Batch and Flow
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-18 DOI: 10.1021/acs.orglett.5c00148
Zeynep Saglam, Shuyu Liu, Yiding Chen, Loïc R. E. Pantaine, Matthew G. Lloyd, Aaron J. Senior
{"title":"Preparation of 2-Heteroaryl-indolin-3-ones by Acid-Mediated Intramolecular Cyclization in Batch and Flow","authors":"Zeynep Saglam, Shuyu Liu, Yiding Chen, Loïc R. E. Pantaine, Matthew G. Lloyd, Aaron J. Senior","doi":"10.1021/acs.orglett.5c00148","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00148","url":null,"abstract":"An intramolecular cyclization strategy to synthesize nitrogen-rich and biologically important 2-heteroaryl-indolin-3-ones has been developed in both batch and flow. Using high-throughput screening, citric acid in a dimethylformamide/water mixture was found to facilitate the reaction under batch conditions, which can tolerate substituted phenyl rings, quinolines, and naphthalenes with a variety of electronic and steric properties. The reaction was reoptimized for flow conditions using design of experiments, complementing the batch conditions for some substrates with greatly reduced reaction times.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"64 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435538","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Correction to “Reaction of Donor–Acceptor α-Diazo Esters and N,N-Dimethylformamide/γ-Lactams to Generate α-Amino-α-aroylethanoates”
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-18 DOI: 10.1021/acs.orglett.5c00415
Xiaonan Mu, Yulong Niu, Minhui Guan, Hao Chen, Chuan-Ying Li, Lei Wang
{"title":"Correction to “Reaction of Donor–Acceptor α-Diazo Esters and N,N-Dimethylformamide/γ-Lactams to Generate α-Amino-α-aroylethanoates”","authors":"Xiaonan Mu, Yulong Niu, Minhui Guan, Hao Chen, Chuan-Ying Li, Lei Wang","doi":"10.1021/acs.orglett.5c00415","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00415","url":null,"abstract":"In the published manuscript, a related paper should be cited as ref 13(c): <contrib-group person-group-type=\"allauthors\"><span>Xiao, K.</span>; <span>Luo, J.</span>; <span>Ye, K.</span>; <span>Wang, Y.</span>; <span>Huang, P.</span></contrib-group> Direct, One-pot Sequential Reductive Alkylation of Lactams/Amides with Grignard and Organolithium Reagents through Lactam/Amide Activation. <cite><i>Angew. Chem., Int. Ed.</i></cite> <span>2010</span>, <em>49</em>, 3037–3040 10.1002/anie.201000652</pub-id>. This article has not yet been cited by other publications.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"34 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435539","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Highly Stereoselective Synthesis of α-Oxoketene N,X-Acetals (X = O, S, or N) under Mild Conditions
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-17 DOI: 10.1021/acs.orglett.5c00174
Jia-Cheng Li, Jia-Wang Li, Rui Zhang, Dewen Dong
{"title":"Highly Stereoselective Synthesis of α-Oxoketene N,X-Acetals (X = O, S, or N) under Mild Conditions","authors":"Jia-Cheng Li, Jia-Wang Li, Rui Zhang, Dewen Dong","doi":"10.1021/acs.orglett.5c00174","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00174","url":null,"abstract":"A straightforward synthesis of α-oxoketene <i>N,X</i>-acetals (<i>X</i> = O, S, or N) from β-oxoamides has been described. The oxyphosphonium intermediates are quickly generated <i>in situ</i> from β-oxoamides in the presence of Hendrickson reagent and triflic anhydride (Tf<sub>2</sub>O) in a chemoselective manner and undergo a chemoselective nucleophilic substitution with phenols, thiophenols, or aromatic amines to deliver the desired products with high stereoselectivity. The one-pot synthetic protocol features readily available starting materials, mild conditions, simple execution, and a wide range of synthetic potentials of the products.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"24 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435541","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Base-Catalyzed Chalcogenative Annulation of N-Maleimido O-Aminobenzyl Alcohol with Elemental Sulfur/Selenium: Access to 1,4-Sulfa-/Selena-zepanes
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-17 DOI: 10.1021/acs.orglett.5c00192
Yuanmin Wen, Teng Liu, Shuntao Huang, Guiyun Zeng, Zhou Zhang, Yanqing Ye, Chao Huang
{"title":"Base-Catalyzed Chalcogenative Annulation of N-Maleimido O-Aminobenzyl Alcohol with Elemental Sulfur/Selenium: Access to 1,4-Sulfa-/Selena-zepanes","authors":"Yuanmin Wen, Teng Liu, Shuntao Huang, Guiyun Zeng, Zhou Zhang, Yanqing Ye, Chao Huang","doi":"10.1021/acs.orglett.5c00192","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00192","url":null,"abstract":"We reported an unprecedented chalcogen element (Se, S) insertion reaction with functionalized aminomaleimide to assemble medium-sized nitrogen-containing organic selenium/sulfur catalyzed by bases. During these [5/6 + 1] tandem annulations, a variety of low-valent inorganic chalcogenides exhibited excellent compatibility, providing a wide scope of structurally diverse 1,4-selenazepanes (17 examples, 60–71% yields), 1,4-benzothiazepines (20 examples, 74–86% yields), and 1,4-thiazines (6 examples, 31–68% yields). The characteristics of this transformation are high atomic economy, formation of two C–Se or C–S bonds in one step, and avoiding the use of unstable and toxic selenium/sulfur reagents under mild conditions.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"1 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143427289","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
From S-Fluoroalkylation to Fluoroalkylation–Thiolation: Difunctionalization of Alkenes with Fluoroalkyl Phenyl Sulfones and Thiophenols Enabled by Photoredox Copper Catalysis
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-17 DOI: 10.1021/acs.orglett.5c00102
Lin Xiao, Zhiqiang Wei, Chuanfa Ni, Alexander D. Dilman, Jinbo Hu
{"title":"From S-Fluoroalkylation to Fluoroalkylation–Thiolation: Difunctionalization of Alkenes with Fluoroalkyl Phenyl Sulfones and Thiophenols Enabled by Photoredox Copper Catalysis","authors":"Lin Xiao, Zhiqiang Wei, Chuanfa Ni, Alexander D. Dilman, Jinbo Hu","doi":"10.1021/acs.orglett.5c00102","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00102","url":null,"abstract":"Molecules containing fluoroalkyl and arylthio groups play a pivotal role in pharmaceutical and agrochemical development. The simultaneous introduction of these functional groups through the 1,2-difunctionalization of alkenes is an efficient strategy. Fluoroalkyl phenyl sulfones serve as accessible fluoroalkyl radical precursors; however, their tendency to interact with thiophenol via the electron donor–acceptor interaction mechanism can impede the desired transformation. Through meticulous selection of solvent and base, we successfully utilized copper catalysis to facilitate an alkene-involved three-component reaction. Our work unveils a photoredox copper-catalyzed fluoroalkylation–thiolation of alkenes using various fluoroalkyl phenyl sulfones (such as perfluoroethyl, tetrafluoroethyl, trifluoromethyl, difluoromethyl, difluoroalkyl, and difluorobenzyl). The efficacy of this approach is exemplified by the synthesis of Kengreal derivatives.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"137 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143427287","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Photosensitized Imino-Thiocyanation of Alkenes
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-17 DOI: 10.1021/acs.orglett.5c00285
Cong Huang, Zhen-Zhen Xie, Jie Gao, Mei Xiang, Hao-Yue Xiang, Kai Chen, Hua Yang
{"title":"Photosensitized Imino-Thiocyanation of Alkenes","authors":"Cong Huang, Zhen-Zhen Xie, Jie Gao, Mei Xiang, Hao-Yue Xiang, Kai Chen, Hua Yang","doi":"10.1021/acs.orglett.5c00285","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00285","url":null,"abstract":"A metal-free photosensitized 1,2-imino-thiocyanation of olefins has been established by using the easily accessible bifunctional reagent <i>S</i>-cyano-<i>N</i>-(diphenylmethylene) thiohydroxylamine. A wide range of olefins were successfully transformed into the corresponding β-iminothiocyanates in moderate to high yields. This protocol stands out for its metal-free nature, broad substrate compatibility, and high atom and step economy, providing an effective strategy for assembling β-amino thiocyanate-containing scaffolds.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"85 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143427315","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Glutathione in the Biosynthesis of Glutazoline Teredinibactins
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-17 DOI: 10.1021/acs.orglett.4c04336
Youjung Sung, Bailey W. Miller, Eric W. Schmidt
{"title":"Glutathione in the Biosynthesis of Glutazoline Teredinibactins","authors":"Youjung Sung, Bailey W. Miller, Eric W. Schmidt","doi":"10.1021/acs.orglett.4c04336","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04336","url":null,"abstract":"Teredinibactins are β-resorcyclic thiazoline dipeptides synthesized by <i>Teredinibacter turnerae</i> T7901, a bacterial symbiont of shipworms in the sea. Through feeding studies, we show that the thiazoline moiety is made from glutathione and its metabolites in a noncanonical pathway, for which we suggest the name “glutazoline”. Mimicking the biosynthetic reaction, we synthesized both natural and unnatural teredinibactins. The results expand the scope of biological and chemical approaches to aromatic azoline conjugates.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"13 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143435540","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Navigating Unexplored Territories of the Interrupted Ugi and Passerini Reactions toward Peptidomimetics
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-02-17 DOI: 10.1021/acs.orglett.4c04810
Paraskevi-Kleio Anastasiou, Michael Fragkiadakis, Maria Thomaidi, Konstantinos G. Froudas, Constantinos G. Neochoritis
{"title":"Navigating Unexplored Territories of the Interrupted Ugi and Passerini Reactions toward Peptidomimetics","authors":"Paraskevi-Kleio Anastasiou, Michael Fragkiadakis, Maria Thomaidi, Konstantinos G. Froudas, Constantinos G. Neochoritis","doi":"10.1021/acs.orglett.4c04810","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04810","url":null,"abstract":"Interrupted reactions redirect established processes, often resulting in unexpected and novel outcomes. By employing a building block containing both acidic and oxo functionalities tethered to the same carbon, we uncovered interrupted variants of the Ugi and Passerini reactions. More than 20 derivatives with a peptide-like framework have been synthesized, demonstrating the broad scope and versatility of these reactions. Additional studies explored the use of various nucleophiles and postmodifications to expand even more the chemical diversity.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"137 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-02-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143427284","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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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