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Salviamone, a norabietane diterpenoid from Salvia roborowskii Maxim and structural revisions of tanshinketolactone and prioketolactone
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-27 DOI: 10.1016/j.tetlet.2025.155519
Mi-Na Yang, Xin Wang, Li-Jia Ye, Le-Le Guo, Yu-Bin Lu, Yi-Nan Yang, Miao Zhang, Zhan-Xin Zhang, Dong-Qing Fei
{"title":"Salviamone, a norabietane diterpenoid from Salvia roborowskii Maxim and structural revisions of tanshinketolactone and prioketolactone","authors":"Mi-Na Yang,&nbsp;Xin Wang,&nbsp;Li-Jia Ye,&nbsp;Le-Le Guo,&nbsp;Yu-Bin Lu,&nbsp;Yi-Nan Yang,&nbsp;Miao Zhang,&nbsp;Zhan-Xin Zhang,&nbsp;Dong-Qing Fei","doi":"10.1016/j.tetlet.2025.155519","DOIUrl":"10.1016/j.tetlet.2025.155519","url":null,"abstract":"<div><div>One norabietane diterpenoid named salviamone (<strong>1</strong>) was isolated from the whole plants of <em>Salvia roborowskii</em> Maxim. Comparison of spectrometric data of <strong>1</strong> with the data of the previously reported tanshinketolactone and prioketolactone, strongly suggested that these metabolites were identical. Due to the existence of many quaternary carbons, we cannot fully determine the planar structure of these compounds through the 2D NMR spectrometric data. Thus, we suggested the structures of tanshinketolactone and prioketolactone were revised to salviamone by an analysis of statistical DP4+ analyses based on DFT-GIAO NMR calculations. Furthermore, the absolute configuration of <strong>1</strong> was determined for the first time by quantum chemistry ECD calculations.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155519"},"PeriodicalIF":1.5,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143507960","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
Alkylcyanation of unactivated alkenes via photoinduced hydrogen atom transfer and 1,4-cyano migration
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-27 DOI: 10.1016/j.tetlet.2025.155516
Meichen Xu , Pandaram Sakthivel , Zongyang Ma , Juntao Ye
{"title":"Alkylcyanation of unactivated alkenes via photoinduced hydrogen atom transfer and 1,4-cyano migration","authors":"Meichen Xu ,&nbsp;Pandaram Sakthivel ,&nbsp;Zongyang Ma ,&nbsp;Juntao Ye","doi":"10.1016/j.tetlet.2025.155516","DOIUrl":"10.1016/j.tetlet.2025.155516","url":null,"abstract":"<div><div>1,2-Dicarbofunctionalization of alkenes represents a step-economical strategy for introducing two functional groups simultaneously in organic synthesis. Herein, we report a visible-light-driven alkylcyanation of unactivated alkenes via hydrogen atom transfer (HAT) and cyano migration. Mechanistic studies suggest that a quinuclidineboryl radical serves as an effective hydridic HAT catalyst, facilitating the generation of electrophilic alkyl radicals. This method features mild reaction conditions and good compatibility with a diverse array of functional groups.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155516"},"PeriodicalIF":1.5,"publicationDate":"2025-02-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143550725","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
Asymmetric Mannich reactions of α-ketoesters catalyzed through noncovalent interactions: Differences between pyruvates and substituted pyruvates in the formation of nucleophilic species
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-22 DOI: 10.1016/j.tetlet.2025.155514
Santanu Mondal, Fujie Tanaka
{"title":"Asymmetric Mannich reactions of α-ketoesters catalyzed through noncovalent interactions: Differences between pyruvates and substituted pyruvates in the formation of nucleophilic species","authors":"Santanu Mondal,&nbsp;Fujie Tanaka","doi":"10.1016/j.tetlet.2025.155514","DOIUrl":"10.1016/j.tetlet.2025.155514","url":null,"abstract":"<div><div>Diastereo- and enantioselective Mannich reactions of substituted pyruvates or α-ketoester derivatives that are larger than 2-oxopropanoates catalyzed by a tertiary amine derivative bearing functional groups that can form hydrogen bonds are described. γ-Amino β-substituted α-ketoesters were obtained with high diastereo- and enantioselectivities. Whereas substituted pyruvates did not react with imines in the presence of the catalyst system composed of a primary amine derivative and an acid that was previously used for the catalysis of Mannich reactions of ethyl pyruvate via the formation of an enamine, the use of the tertiary amine derivative bearing functional groups that can form hydrogen bonds enabled the activation of substituted pyruvates, leading to the formation of the desired Mannich reaction products.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155514"},"PeriodicalIF":1.5,"publicationDate":"2025-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143487928","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Three new alkaloids from Corydalis saxicola and their antiproliferative activity
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-22 DOI: 10.1016/j.tetlet.2025.155513
Mei-Shan Li , Li Luo , Gang Wei , Xi-Xi Song , Hai-Ying Luo , Heng-Shan Wang , Jia-Zi Luo
{"title":"Three new alkaloids from Corydalis saxicola and their antiproliferative activity","authors":"Mei-Shan Li ,&nbsp;Li Luo ,&nbsp;Gang Wei ,&nbsp;Xi-Xi Song ,&nbsp;Hai-Ying Luo ,&nbsp;Heng-Shan Wang ,&nbsp;Jia-Zi Luo","doi":"10.1016/j.tetlet.2025.155513","DOIUrl":"10.1016/j.tetlet.2025.155513","url":null,"abstract":"<div><div>Three undescribed protoberberine alkaloids, named corydalisine L-N, along with four known compounds, were isolated from <em>Corydalis saxicola</em>. Their structures were accurately characterized using nuclear magnetic resonance (NMR) and mass spectrometry (MS). The absolute configurations were determined through the calculation of electronic circular dichroism (ECD). Compounds 1–3 were relatively rare 8,13-dicarbonyl protoberbine alkaloids, which are uncommon in plants of the genus Corydalis. All compounds were evaluated for their cytotoxicity against four human cancer cell lines.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155513"},"PeriodicalIF":1.5,"publicationDate":"2025-02-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143507958","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 and antibacterial applications of Gemini-QA N-chloramines with rigid spacer
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-21 DOI: 10.1016/j.tetlet.2025.155512
Lingdong Li, Weilun Zhang, Pengfei Liu, Suyuan Liu, Zhongtian Du, Hao Zhou
{"title":"Synthesis and antibacterial applications of Gemini-QA N-chloramines with rigid spacer","authors":"Lingdong Li,&nbsp;Weilun Zhang,&nbsp;Pengfei Liu,&nbsp;Suyuan Liu,&nbsp;Zhongtian Du,&nbsp;Hao Zhou","doi":"10.1016/j.tetlet.2025.155512","DOIUrl":"10.1016/j.tetlet.2025.155512","url":null,"abstract":"<div><div>Starting from piperazine and diazabicyclooctane respectively, two series of Gemini-quaternary ammonium (QA) <em>N</em>-chloramines <strong>6–9</strong> and <strong>10–13</strong> were synthesized with rigid spacer embedded via ploy-step synthesis strategy. Preliminary antibacterial data showed that “team effort” biocidal effect was observed for resultant <em>N</em>-chloramines, and <strong>6</strong> exhibited superior antibacterial efficacy in contrast with <strong>10</strong>. In addition, the linker length plays a decisive role in biocidal performance and <strong>9</strong>/<strong>13</strong> (linker as -(CH<sub>2</sub>)<sub>10</sub>-) achieved the highest efficacy. Our results may inspire exploration of new generation of <em>N</em>-chloramine biocides with more potent bactericidal activity.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155512"},"PeriodicalIF":1.5,"publicationDate":"2025-02-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143520424","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
Investigation and optimization of metal- and organocatalyzed decarboxylative radical addition of carboxylic acids to Seebach-Beckwith dehydroalanine towards optically pure unnatural amino acids
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-20 DOI: 10.1016/j.tetlet.2025.155507
Ilia Perov, Karizza F. Catenza, Jose Jr. Abucay, Yu-Ting Hsiao, John C. Vederas
{"title":"Investigation and optimization of metal- and organocatalyzed decarboxylative radical addition of carboxylic acids to Seebach-Beckwith dehydroalanine towards optically pure unnatural amino acids","authors":"Ilia Perov,&nbsp;Karizza F. Catenza,&nbsp;Jose Jr. Abucay,&nbsp;Yu-Ting Hsiao,&nbsp;John C. Vederas","doi":"10.1016/j.tetlet.2025.155507","DOIUrl":"10.1016/j.tetlet.2025.155507","url":null,"abstract":"<div><div>Four decarboxylative conjugate radical addition methods, including recent and greener methods using Fe- and Eosin Y as photocatalysts, were examined using Seebach-Beckwith dehydroalanine as a radical acceptor. Head-to-head comparison of yields and purity suggests that Ir-photocatalyzed decarboxylation of carboxylic acids is the optimal method for syntheses involving resonance-stabilized radicals. However, approaches relying on cheaper Ni-, Fe-, and Eosin Y-catalyzed processes are quite viable for the conjugate addition of 1°, 2°, and 3° radicals.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"159 ","pages":"Article 155507"},"PeriodicalIF":1.5,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143507959","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Vicinal diphosphorylation of enaminones with diaryl phosphine oxides via AlCl3-mediated CN bond cleavage
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-20 DOI: 10.1016/j.tetlet.2025.155472
Xin Jin , Yong An , Jia Chen , Xianheng Wang , Huabin Wang , Changkuo Zhao , Qiang Huang
{"title":"Vicinal diphosphorylation of enaminones with diaryl phosphine oxides via AlCl3-mediated CN bond cleavage","authors":"Xin Jin ,&nbsp;Yong An ,&nbsp;Jia Chen ,&nbsp;Xianheng Wang ,&nbsp;Huabin Wang ,&nbsp;Changkuo Zhao ,&nbsp;Qiang Huang","doi":"10.1016/j.tetlet.2025.155472","DOIUrl":"10.1016/j.tetlet.2025.155472","url":null,"abstract":"<div><div>A vicinal diphosphorylation of enaminones with diaryl phosphine oxides have been established condition through AlCl<sub>3</sub> as Lewis acid in this work. The transformation features excellent functional group tolerance, operational simplicity, and high yields, which provides an alternative strategy for accessing various diphosphoryl products <strong>3a</strong>. Preliminary mechanism studies suggest the conversion between <strong>1a</strong> and <strong>2a</strong> involves the elimination of dimethylamine and cascade vicinal addition. This research provides significant value to the vicinal functionalization of enaminones.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155472"},"PeriodicalIF":1.5,"publicationDate":"2025-02-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143445859","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
Post-Ugi cyclization approach for transition metal-free synthesis of Azetidine derivatives
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-18 DOI: 10.1016/j.tetlet.2025.155509
Rozita Yazzaf , Mohammad Hosein Sayahi , Mohammad Mahdavi
{"title":"Post-Ugi cyclization approach for transition metal-free synthesis of Azetidine derivatives","authors":"Rozita Yazzaf ,&nbsp;Mohammad Hosein Sayahi ,&nbsp;Mohammad Mahdavi","doi":"10.1016/j.tetlet.2025.155509","DOIUrl":"10.1016/j.tetlet.2025.155509","url":null,"abstract":"<div><div>A novel, metal-free strategy has been developed for the efficient synthesis of unique azetidine derivatives via a post-Ugi cyclization. This method involves generating 4-component Ugi adducts by reacting aldehydes, isocyanides, primary propargylamine, and 2-(phenylamino) benzoic acid. In the subsequent post-Ugi cyclization, azetidine derivatives are synthesized through a nucleophilic attack of a carbanion on the alkyne, followed by an intramolecular cyclization that forms a new carbon‑carbon bond.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155509"},"PeriodicalIF":1.5,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143437737","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
Stabilization and structure elucidation of unstable Corynoxine-type stereoisomers using tartaric acid
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-18 DOI: 10.1016/j.tetlet.2025.155510
Yuta Koseki , Ryosuke Sugiyama , Soichiro Nishimura , Takako Sugahara , Ryuji Asano , Mami Yamazaki , Katsuyuki Aoki
{"title":"Stabilization and structure elucidation of unstable Corynoxine-type stereoisomers using tartaric acid","authors":"Yuta Koseki ,&nbsp;Ryosuke Sugiyama ,&nbsp;Soichiro Nishimura ,&nbsp;Takako Sugahara ,&nbsp;Ryuji Asano ,&nbsp;Mami Yamazaki ,&nbsp;Katsuyuki Aoki","doi":"10.1016/j.tetlet.2025.155510","DOIUrl":"10.1016/j.tetlet.2025.155510","url":null,"abstract":"<div><div>In oxindole alkaloids, stereoisomer formation occurs via bond cleavage at the spiro carbon center, followed by an intramolecular Mannich reaction. Since the possible common transition state possesses two prochiral faces, four stereoisomers at the C-3 and C-7 positions are potentially generated; however, few have been reported in nature. In this study, the four corynoxine stereoisomers were isolated, and their structures were elucidated. Two of these stereoisomers were found to be structurally unstable. Addtion of tartaric acid as a chemical trap reagent stabilized these isomers named corynoxines C and D and revealed their stereochemistries as 3<em>R</em>, 7<em>S</em> and 3<em>R</em>, 7<em>R</em>, respectively.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155510"},"PeriodicalIF":1.5,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143437736","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
Visible-light promoted radical coupling of difluoroenol silyl ethers and difluorinated Pyf-sulfides to construct tetrafluoroethylene-containing compounds
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-16 DOI: 10.1016/j.tetlet.2025.155505
Chen Wang , Zhihua Wang , Jinliang Zhang , Miaomiao Mu , Jin Zhang , Zhiming Wang , Jianguo Yang , Guobo Huang , Xiaolei Zhu
{"title":"Visible-light promoted radical coupling of difluoroenol silyl ethers and difluorinated Pyf-sulfides to construct tetrafluoroethylene-containing compounds","authors":"Chen Wang ,&nbsp;Zhihua Wang ,&nbsp;Jinliang Zhang ,&nbsp;Miaomiao Mu ,&nbsp;Jin Zhang ,&nbsp;Zhiming Wang ,&nbsp;Jianguo Yang ,&nbsp;Guobo Huang ,&nbsp;Xiaolei Zhu","doi":"10.1016/j.tetlet.2025.155505","DOIUrl":"10.1016/j.tetlet.2025.155505","url":null,"abstract":"<div><div>A visible-light promoted radical coupling of difluoroenol silyl ethers and difluorinated Pyf-sulfides has been developed. This protocol provides a simple and straightforward approach to assemble diverse functionalized tetrafluoroethylene-containing compounds in moderate to good yields.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155505"},"PeriodicalIF":1.5,"publicationDate":"2025-02-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143511826","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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