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Rearranged and enantiomeric alkaloids from Cephalotaxus sinensis
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155437
Jing Wu , Xin-Yu Liu , Mei-Fen Bao , Bao-Bao Shi , Ming-Xiang Li , Xiang-Hai Cai
{"title":"Rearranged and enantiomeric alkaloids from Cephalotaxus sinensis","authors":"Jing Wu ,&nbsp;Xin-Yu Liu ,&nbsp;Mei-Fen Bao ,&nbsp;Bao-Bao Shi ,&nbsp;Ming-Xiang Li ,&nbsp;Xiang-Hai Cai","doi":"10.1016/j.tetlet.2024.155437","DOIUrl":"10.1016/j.tetlet.2024.155437","url":null,"abstract":"<div><div>Three undescribed alkaloids (<strong>1</strong>–<strong>3</strong>) along with 30 known ones were isolated from the twigs and leaves of <em>Cephalotaxus sinensis</em>. The structures of the new alkaloids were determined through comprehensive spectroscopic analysis and ECD calculations. Cephalosinine A (<strong>1</strong>) with 6/6/6/5 ring system represents a new type of <em>Cephalotaxus</em> alkaloid, which might be formed through a rearrangement from simultaneously isolated cephalotaxinone. Cephalolancine B (<strong>2</strong>) was the second cephalolancine skeleton alkaloid. (+)-Acetylcephalotaxine <em>β</em>-<em>N</em>-oxide (<strong>3</strong>) was an enantiomeric <em>Cephalotaxus</em> alkaloid. The isolated homoerythrina-type alkaloids were evaluated for their <em>in vitro</em> hearing protective effects against neomycin-induced cell death in HEI-OC-1 cells.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155437"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159671","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
Highly diastereoselective total synthesis of Vibegron, a drug for overactive bladder disease
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155429
D.R. Adarsh , T. Ravi Teja , B. Sridhar , B.V. Subba Reddy
{"title":"Highly diastereoselective total synthesis of Vibegron, a drug for overactive bladder disease","authors":"D.R. Adarsh ,&nbsp;T. Ravi Teja ,&nbsp;B. Sridhar ,&nbsp;B.V. Subba Reddy","doi":"10.1016/j.tetlet.2024.155429","DOIUrl":"10.1016/j.tetlet.2024.155429","url":null,"abstract":"<div><div>A highly efficient and practical approach to the total synthesis of Vibegron, a drug for overactive bladder disease has been achieved <em>through</em> a substrate-directed diastereoselective reduction of ketone to <em>syn-</em>1,2-amino alcohol, enabling the synthesis of Vibegron in a highly stereoselective manner. Another key step involved in this approach is the formation of a <em>cis</em>-pyrrolidine ring <em>via</em> the sequential one-pot Pd/C-catalyzed olefin reduction, debenzylation, Cbz deprotection and reductive amination/cyclization. The total synthesis of Vibegron has been achieved in nine steps with an overall yield of 36 % starting from a readily available <span>d</span>-Serine. It is a non-enzymatic and alternate process to previous approaches.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155429"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143160318","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 ε-regioselective conjugate addition of 2-furfuryl ketones to nitroalkenes using a thiourea organocatalyst
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155392
Taro Koda , Hiroshi Akutsu , Mitsuaki Suzuki , Kosuke Nakashima , Shin-ichi Hirashima , Akihiro Yoshida , Tsuyoshi Miura , Takashi Yamanoi
{"title":"Asymmetric ε-regioselective conjugate addition of 2-furfuryl ketones to nitroalkenes using a thiourea organocatalyst","authors":"Taro Koda ,&nbsp;Hiroshi Akutsu ,&nbsp;Mitsuaki Suzuki ,&nbsp;Kosuke Nakashima ,&nbsp;Shin-ichi Hirashima ,&nbsp;Akihiro Yoshida ,&nbsp;Tsuyoshi Miura ,&nbsp;Takashi Yamanoi","doi":"10.1016/j.tetlet.2024.155392","DOIUrl":"10.1016/j.tetlet.2024.155392","url":null,"abstract":"<div><div>The asymmetric ε-regioselective conjugate addition of 2-furfuryl ketones to nitroalkenes using a pyrrolidine–thiourea organocatalyst yielded ε-regioselective addition products in high yields with high enantioselectivities. This work represents the first example of asymmetric ε-regioselective conjugate addition of 2-furfuryl ketones to nitroalkenes.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155392"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159582","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
An alcohol thioetherification method utilizing a domino dual catalysis strategy
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155433
Zhe Wang , Xinyuan Hu , Chuqiao Song , Honghong Su , Chuanwu Xiong , Guoliang Chen , Xuefei Bao
{"title":"An alcohol thioetherification method utilizing a domino dual catalysis strategy","authors":"Zhe Wang ,&nbsp;Xinyuan Hu ,&nbsp;Chuqiao Song ,&nbsp;Honghong Su ,&nbsp;Chuanwu Xiong ,&nbsp;Guoliang Chen ,&nbsp;Xuefei Bao","doi":"10.1016/j.tetlet.2024.155433","DOIUrl":"10.1016/j.tetlet.2024.155433","url":null,"abstract":"<div><div>Thioethers are prevalent in pharmaceuticals, and its synthetic method utilizing alcohols are receiving more attention due to its environmental benign property. Here, a metal-free dehydrative thioetherification method was reported, enabling the conversion of various alcohols into thioethers via a domino dual catalysis strategy including catalyzed Mitsunobu reaction and followed nucleophilic substitution. Although this method cannot provide satisfactory yields for certain alcohols, it improves the substrate scope of alcohol thioetherification to general primary and secondary alcohols. By employing phosphine oxide and triflic acid as catalysts, 16 phenyl thioethers were synthesized with low to moderate yields via the Dean-Stark distillation. Moreover, the above results indicate that the yield and substrate scope of this method could be enhanced by improving the catalytic rate of the phosphine oxide.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155433"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159585","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
Pd(II)-catalyzed hydroxy group directed synthesis of spiro-fused succinimide isochromenochromenones
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155434
Kongkona Gogoi , Bondana Bora , Geetika Borah , Sanjib Gogoi
{"title":"Pd(II)-catalyzed hydroxy group directed synthesis of spiro-fused succinimide isochromenochromenones","authors":"Kongkona Gogoi ,&nbsp;Bondana Bora ,&nbsp;Geetika Borah ,&nbsp;Sanjib Gogoi","doi":"10.1016/j.tetlet.2024.155434","DOIUrl":"10.1016/j.tetlet.2024.155434","url":null,"abstract":"<div><div>A new annulation reaction is developed for the synthesis of isochromene fused chromenones possessing spiro succinimides scaffold. In this hydroxyl group directed Pd(II)-catalyzed reaction, easily affordable 3-hydroxy-2-phenyl-chromenones and maleimides were used as the coupling partners to synthesize a wide range of the biologically relevant spirocyclic compounds.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155434"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143160317","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 Diels–Alder reaction of heterocyclic o-quinodimethane with 2-arylidene-1,3-indanedoines to access tetrahydrospirocarbazole-indanediones via trienamine intermediate
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155428
Raghupathi Mutyala , K. Rajitha , Jagadeesh Babu Nanubolu , Rajesh Chandra
{"title":"Asymmetric Diels–Alder reaction of heterocyclic o-quinodimethane with 2-arylidene-1,3-indanedoines to access tetrahydrospirocarbazole-indanediones via trienamine intermediate","authors":"Raghupathi Mutyala ,&nbsp;K. Rajitha ,&nbsp;Jagadeesh Babu Nanubolu ,&nbsp;Rajesh Chandra","doi":"10.1016/j.tetlet.2024.155428","DOIUrl":"10.1016/j.tetlet.2024.155428","url":null,"abstract":"<div><div>Enantioselective Diels–Alder reaction of <em>in situ</em> generated heterocyclic quinodimethane from indolylacrylaldehyde with arylidine-1,3-indanedinones is carried out in the presence of chiral prolinol-derived catalysts. The reaction proceeds through a trienamine pathway, resulting in chiral tetrahydrospirocarbazoles-indane-1,3-diones. The reaction proceeds with high to excellent <em>enantio</em>- and diasteroselectivities with excellent yields.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155428"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143160362","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 CH alkylation of N-heterocycles via aromatization-driven CC fragmentation of unstrained ketones
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155440
Peng Ye , Yu-Yan Xiong , Bo Zhang
{"title":"Electrochemical CH alkylation of N-heterocycles via aromatization-driven CC fragmentation of unstrained ketones","authors":"Peng Ye ,&nbsp;Yu-Yan Xiong ,&nbsp;Bo Zhang","doi":"10.1016/j.tetlet.2024.155440","DOIUrl":"10.1016/j.tetlet.2024.155440","url":null,"abstract":"<div><div>Herein, we report an electrochemically driven direct C<img>H alkylation of <em>N</em>-heterocycles using readily accessible pro-aromatic dihydroquinazolinones derived from simple ketones as alkylating reagents. This protocol employs an operationally simple undivided cell and inexpensive materials, reticulated vitreous carbon (RVC) and magnesium, as the electrodes. Notably, this practical electrochemical approach proceeds under chemical oxidant-free conditions, and a vast array of valuable alkylated <em>N</em>-heterocycles (more than 40 examples), including quinoxalin-2(1<em>H</em>)-ones, azauracils, pyrazinones, quinoxalines, quinazolines, quinolines, and phenanthridines, can be readily constructed at room temperature.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155440"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159584","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
3,4,5,6-Tetrahydro-2H-3,6-epoxybenzo[g][1,4]oxazocine – A new bridged heterocyclic system
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155405
Polina A. Khardina, Evgeny M. Buev, Vladimir S. Moshkin, Vyacheslav Y. Sosnovskikh
{"title":"3,4,5,6-Tetrahydro-2H-3,6-epoxybenzo[g][1,4]oxazocine – A new bridged heterocyclic system","authors":"Polina A. Khardina,&nbsp;Evgeny M. Buev,&nbsp;Vladimir S. Moshkin,&nbsp;Vyacheslav Y. Sosnovskikh","doi":"10.1016/j.tetlet.2024.155405","DOIUrl":"10.1016/j.tetlet.2024.155405","url":null,"abstract":"<div><div>Salicylic aldehydes readily undergo alkylation with bromoacetaldehyde diethyl acetal, subsequent [3+2]-cycloaddition with nonstabilized azomethine ylide and consequent hydrolysis of the oxazolidine and acetal groups leads to 4-methyl and 4-benzyl-3,4,5,6-tetrahydro-2<em>H</em>-3,6-epoxybenzo[<em>g</em>][1,4]oxazocines in 15–65 % overall yields. <em>N</em>-Unsubstituted oxazocines were prepared by the Henry reaction of the alkylated salicylic aldehydes followed by reduction and hydrolysis in 22–40 % overall yields based on starting salicylic aldehyde.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155405"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159588","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
Recent advances in the electrophilic halogenation of aromatic compounds using N-halosuccinimides (NXS)
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155419
Kiyoshi Tanemura
{"title":"Recent advances in the electrophilic halogenation of aromatic compounds using N-halosuccinimides (NXS)","authors":"Kiyoshi Tanemura","doi":"10.1016/j.tetlet.2024.155419","DOIUrl":"10.1016/j.tetlet.2024.155419","url":null,"abstract":"<div><div>Halogenation of aromatic compounds is one of the most crucial reactions in modern synthetic chemistry. Aromatic halides are important synthetic intermediates used in metal-catalyzed cross-coupling reactions, substitution reactions, and the preparation of drugs and natural products. Continuous efforts have been devoted to the synthesis of aryl halides. This review summarizes the recent progress in the Brønsted/Lewis acid or Lewis base-catalyzed halogenation of aromatic compounds using <em>N</em>-halosuccinimides (NXS) over the past six years. In particular, it focuses on substrate scope, reaction mechanisms, and future challenges.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155419"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159583","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
Formation of triarylphosphines via PH/CF cross coupling reactions catalyzed by nickel
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155445
Meng-Ting Xiang , Lei Fan , Qian Xu , Li Zhang , Shuai Wang , Hong Zhong , Jia Yang
{"title":"Formation of triarylphosphines via PH/CF cross coupling reactions catalyzed by nickel","authors":"Meng-Ting Xiang ,&nbsp;Lei Fan ,&nbsp;Qian Xu ,&nbsp;Li Zhang ,&nbsp;Shuai Wang ,&nbsp;Hong Zhong ,&nbsp;Jia Yang","doi":"10.1016/j.tetlet.2024.155445","DOIUrl":"10.1016/j.tetlet.2024.155445","url":null,"abstract":"<div><div>Herein, a nickel-catalyzed coupling reaction of monofluoroarenes or polyfluoroarenes with diphenyl phosphine to construct C(sp<sup>2</sup>)<img>P bond through C<img>F bond functionalization is disclosed. The reaction can be carried out successfully to produce the corresponding triarylphosphine or fluorinated triarylphosphine compounds with good to high yields, providing a new method for the synthesis of fluorine-containing organophosphine compounds via the formation of C<img>P bond.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155445"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159668","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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