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Asymmetric Total Synthesis of Isolinearol Using Low-Valence Titanium and Evaluation of Its Inhibitory Activity against Mussel Byssal Thread Formation
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-25 DOI: 10.1021/acs.orglett.4c04309
Tomoki Tsuruta, Keisuke Nishikawa, Yukika Yoshino, Daiki Osada, Tatsuhide Miwa, Kazumi Nimura, Takashi Kamada, Yoshiki Morimoto
{"title":"Asymmetric Total Synthesis of Isolinearol Using Low-Valence Titanium and Evaluation of Its Inhibitory Activity against Mussel Byssal Thread Formation","authors":"Tomoki Tsuruta, Keisuke Nishikawa, Yukika Yoshino, Daiki Osada, Tatsuhide Miwa, Kazumi Nimura, Takashi Kamada, Yoshiki Morimoto","doi":"10.1021/acs.orglett.4c04309","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04309","url":null,"abstract":"The asymmetric total synthesis of isolinearol, a <i>seco</i>-dolastane-type diterpenoid that inhibits byssal thread formation by mussels, has been achieved. In the synthesis, the key features include an intramolecular reductive nucleophilic addition using a low-valence titanium species and the direct installation of a ketone side chain. We evaluated their biological activities using the synthetic samples and found the novel inhibitory molecules with a simplified structure exhibit high inhibitory activities against byssus formation and low toxicities.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"38 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143030890","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
Enantioselective Synthesis of Chiral 2,2-Difluoro-spiroindanone-dihydroquinazolinones by CPA-Catalyzed Cyclization Reactions
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-25 DOI: 10.1021/acs.orglett.5c00043
Xing-Pin Wei, Fen Gao, Dan Li, Yonghui He, Ganpeng Li, Xiao-Jing Zhao
{"title":"Enantioselective Synthesis of Chiral 2,2-Difluoro-spiroindanone-dihydroquinazolinones by CPA-Catalyzed Cyclization Reactions","authors":"Xing-Pin Wei, Fen Gao, Dan Li, Yonghui He, Ganpeng Li, Xiao-Jing Zhao","doi":"10.1021/acs.orglett.5c00043","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00043","url":null,"abstract":"The synthesis of chiral <i>gem</i>-difluorinated spiro-heterocyclic compounds continues to be a significant challenge in organic chemistry due to their widespread applications across various fields. Therefore, efficient asymmetric approaches for the synthesis of <i>gem</i>-difluorinated spiroindanone-dihydroquinazolinones are particularly valuable, especially in the industrial manufacturing of chiral fluorinated drugs. Herein, we developed the CPA-catalyzed asymmetric enantioselective cyclization reactions of <i>gem</i>-difluoroalkyl 1,3-indandiones with anthranilamides to achieve various chiral 2,2-difluoro-spiroindanone-dihydroquinazolinones in good to high yields with excellent enantioselectivities. Moreover, the mechanism experiment proved that the <i>gem</i>-difluoro substitution pattern promotes the reaction.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"23 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143030891","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
Synthesis of 1,4-Diketones from Esters Enabled by a Tetraborylethane Reagent
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-25 DOI: 10.1021/acs.orglett.4c04690
Miaomiao Wu, Tongchang Fang, Liangxuan Xu, Qingfeng Xu, Jianmei Lu, Chao Liu
{"title":"Synthesis of 1,4-Diketones from Esters Enabled by a Tetraborylethane Reagent","authors":"Miaomiao Wu, Tongchang Fang, Liangxuan Xu, Qingfeng Xu, Jianmei Lu, Chao Liu","doi":"10.1021/acs.orglett.4c04690","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04690","url":null,"abstract":"A modular synthesis method for 1,4-diketones has been developed. Utilizing inexpensive carboxylic acid esters as carbonyl sources and tetraborylethane (<b>TBE</b>) as a nucleophilic reagent, a one-pot strategy for constructing two C–C bonds was established. Notably, this reaction proceeds without the involvement of transition metals and exhibits excellent functional group compatibility. A diverse array of α-substituted 1,4-diketones were synthesized using various electrophiles for capture.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"2 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143030700","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 Regioselective Synthesis of Spiroimidazolidinones via a Sequential Ugi 4CR/Azide-Isocyanide Coupling/Cyclization/Rearrangement/Hydroxylation Reaction
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-24 DOI: 10.1021/acs.orglett.4c04742
Yan-Mei Yan, Hong-Bo Tong, Zhen-Xing Ren, Hong-Li Zhang, Jiao Wang, Ying-Chun He, Yong-Zhao Wang
{"title":"One-Pot Regioselective Synthesis of Spiroimidazolidinones via a Sequential Ugi 4CR/Azide-Isocyanide Coupling/Cyclization/Rearrangement/Hydroxylation Reaction","authors":"Yan-Mei Yan, Hong-Bo Tong, Zhen-Xing Ren, Hong-Li Zhang, Jiao Wang, Ying-Chun He, Yong-Zhao Wang","doi":"10.1021/acs.orglett.4c04742","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04742","url":null,"abstract":"Herein a novel and robust methodology to spiroimidazolidinones has been developed under a mild reaction. The reaction of (Z)-2-azido-3-phenylacrylic acids <b>1</b>, aldehydes <b>2</b>, amines <b>3</b>, isocyanides <b>4</b>, and isocyanides <b>6</b> produced regioselectively spiroimidazolidinones in 71–88% yields via a sequential Ugi 4CR/Pd(0) catalyzed azide-isocyanide coupling/cyclization/rearrangement/hydroxylation reaction. Furthermore, the easily accessible starting materials, high bond-forming efficiency, and broad substituent tolerance make this strategy useful in synthetic and medicinal chemistry.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"19 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143030893","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
Nickel-Catalyzed Cyclization/Carbonylation Reaction of N-Allylbromoacetamides with Arylboronic Acids toward 2-Pyrrolidinones
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-24 DOI: 10.1021/acs.orglett.5c00003
Hucheng Ma, Chen-Yang Hou, Ruyi Zhao, Xinxin Qi, Xiao-Feng Wu
{"title":"Nickel-Catalyzed Cyclization/Carbonylation Reaction of N-Allylbromoacetamides with Arylboronic Acids toward 2-Pyrrolidinones","authors":"Hucheng Ma, Chen-Yang Hou, Ruyi Zhao, Xinxin Qi, Xiao-Feng Wu","doi":"10.1021/acs.orglett.5c00003","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c00003","url":null,"abstract":"A straightforward and efficient nickel-catalyzed cyclization/carbonylation transformation of <i>N</i>-allylbromoacetamides toward the synthesis of 2-pyrrolidinone derivatives has been developed with arylboronic acids as the reaction partner. This transformation proceeds through a sequential single-electron-transfer pathway via 5-<i>exo</i>-<i>trig</i> cyclization and carbonyl insertion steps, furnishing a variety of 2-pyrrolidinone derivatives in good yields. Various useful functional groups were well tolerated. Moreover, formic acid is applied as the CO source here with nickel as the catalyst, which provides a good supplement for carbonylation chemistry and heterocycle synthesis.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"13 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143030894","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
Isolation and Total Synthesis of Ukabamide, an Antitrypanosomal Lipopeptide from a Marine Moorena sp. Cyanobacterium
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-24 DOI: 10.1021/acs.orglett.4c04832
Masahiro Hagihara, Naoaki Kurisawa, Arihiro Iwasaki, Raimu Taguchi, Ghulam Jeelani, Tomoyoshi Nozaki, Kiyotake Suenaga
{"title":"Isolation and Total Synthesis of Ukabamide, an Antitrypanosomal Lipopeptide from a Marine Moorena sp. Cyanobacterium","authors":"Masahiro Hagihara, Naoaki Kurisawa, Arihiro Iwasaki, Raimu Taguchi, Ghulam Jeelani, Tomoyoshi Nozaki, Kiyotake Suenaga","doi":"10.1021/acs.orglett.4c04832","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04832","url":null,"abstract":"Human African trypanosomiasis (HAT) is one of the most lethal of the neglected tropical diseases. While the discovery of a novel antitrypanosomal drug is highly desired, the creation of a superior lead compound is challenging. Herein we report ukabamide (<b>1</b>), which was isolated from a marine <i>Moorena</i> sp. cyanobacterium, as a selective and potent antitrypanosomal lipopeptide (IC<sub>50</sub> = 34 ± 18 nM against <i>Trypanosoma brucei rhodesiense</i>). Its structure was elucidated by spectroscopic analyses and degradation reactions and confirmed by total synthesis. In addition, we prepared two modified analogs and revealed the importance of the fatty acid chain length for biological activity. These findings may provide design guidelines for an antitrypanosomal drug.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"38 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027009","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 Chlorination and Cross-Electrophile Coupling of Alcohols with Aryl Chlorides
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-24 DOI: 10.1021/acs.orglett.4c04676
Benjamin N. Ahern, Daniel J. Weix
{"title":"One-Pot Chlorination and Cross-Electrophile Coupling of Alcohols with Aryl Chlorides","authors":"Benjamin N. Ahern, Daniel J. Weix","doi":"10.1021/acs.orglett.4c04676","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04676","url":null,"abstract":"Although alkyl alcohols and aryl chlorides are the two most abundant substrate pools for cross-electrophile coupling, methods to couple them remain limited. Herein we demonstrate a simple procedure for the in situ deoxychlorination of alcohols followed by XEC with aryl chlorides. A broad substrate scope can be achieved by tuning the rate of the reaction via halide exchange. Key to success is the identification of 1-chloro-<i>N</i>,<i>N</i>,2-trimethyl-1-propenylamine as a mild, noninterfering halogenation reagent.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"2 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027128","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
Access to Chiral Bridged Biaryls via Brønsted Acid-Catalyzed Asymmetric Addition of Alcohols to Fluoroalkylated Biaryl Oxazepines
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-24 DOI: 10.1021/acs.orglett.4c04813
Bowen Zhu, Wei Yuan, Ting Tu, Guimei Dai, Liejin Zhou, Shichao Ren, Xing Yang
{"title":"Access to Chiral Bridged Biaryls via Brønsted Acid-Catalyzed Asymmetric Addition of Alcohols to Fluoroalkylated Biaryl Oxazepines","authors":"Bowen Zhu, Wei Yuan, Ting Tu, Guimei Dai, Liejin Zhou, Shichao Ren, Xing Yang","doi":"10.1021/acs.orglett.4c04813","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04813","url":null,"abstract":"We disclose herein a chiral phosphoric-acid-catalyzed enantioselective addition reaction of alcohols to fluoroalkylated biaryl 1,3-oxoazepines, which furnished a wide range of bridged biaryls bearing a fluoroalkylated quaternary carbon stereocenter on the seven-membered ring in high yields (up to 99%) with excellent enantioselectivities (up to 98% ee). Our method can be used for the modification of several natural products and bioactive molecules. Preliminary studies revealed that the products obtained in this reaction exhibit good in vitro bioactivities against two plant pathogens.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"38 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027000","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
Enantioselective Decarboxylative Mannich Reactions of α,β-Unsaturated β′-Ketoacids and Isatin Imines: Application in the Synthesis of Spiro[indoline-3,2′-piperidine]-2,4′-diones
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-24 DOI: 10.1021/acs.orglett.4c04675
Hrishikesh Devaki Sadanam Venugopal, Sunil V. Pansare
{"title":"Enantioselective Decarboxylative Mannich Reactions of α,β-Unsaturated β′-Ketoacids and Isatin Imines: Application in the Synthesis of Spiro[indoline-3,2′-piperidine]-2,4′-diones","authors":"Hrishikesh Devaki Sadanam Venugopal, Sunil V. Pansare","doi":"10.1021/acs.orglett.4c04675","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04675","url":null,"abstract":"Organocatalytic, enantioselective decarboxylative Mannich reactions of α,β-unsaturated β′-ketoacids and isatin <i>N</i>-Boc imines, to give the corresponding 3-carbamoyl-2-oxindole derivatives, were developed. Subsequent N-deprotection and diastereoselective, intramolecular, aza-Michael reaction of the free amine provides previously unreported spiro[indoline-3,2′-piperidine]-2,4′-diones.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"13 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143027127","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
Copper-Catalyzed Annulation of α,β-Unsaturated Ketoximes with Dialkyl Acetylenedicarboxylates for the Synthesis of Highly Substituted Pyridines
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-24 DOI: 10.1021/acs.orglett.4c04351
Shi-Mei He, Yun-Bo Yang, Lv-Yan Liu, Ning Yu, Yu-Qiang Zhou, Jia-Hao Zhou, Mei-Jun Zheng, Xiao-Kun Jin, Kun Jiang, Ye Wei
{"title":"Copper-Catalyzed Annulation of α,β-Unsaturated Ketoximes with Dialkyl Acetylenedicarboxylates for the Synthesis of Highly Substituted Pyridines","authors":"Shi-Mei He, Yun-Bo Yang, Lv-Yan Liu, Ning Yu, Yu-Qiang Zhou, Jia-Hao Zhou, Mei-Jun Zheng, Xiao-Kun Jin, Kun Jiang, Ye Wei","doi":"10.1021/acs.orglett.4c04351","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04351","url":null,"abstract":"A copper-catalyzed [4 + 2] annulation protocol from readily available α,β-unsaturated ketoximes and dialkyl acetylenedicarboxylates has been achieved. The approach enables the expedient construction of a series of structurally new highly substituted pyridines with good functional group tolerance.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"18 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143026999","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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