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Colletotrichalasin A: a hepatoprotective decalin-tetramic acid derivative featuring a pentacyclic 6/6/5/6/5 ring skeleton from the endophytic fungus Colletotrichum gloeosporioides MT-51 of Huperzia serrata 炭疽菌素A：一种保护肝脏的十钙素四羧酸衍生物，其五环骨架为6/6/5/6/5，来自胡杉属内生真菌炭疽菌MT-51
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-04 DOI: 10.1016/j.tetlet.2025.155691
Bei-Bei Zhang , Hong-Yun Yang , Xiao-Yun Yan , Na Xiong , Lin Zhang , Xiao Liu , Pei-Cheng Zhang , She-Po Shi , Xu Zhang , Juan Wang
{"title":"Colletotrichalasin A: a hepatoprotective decalin-tetramic acid derivative featuring a pentacyclic 6/6/5/6/5 ring skeleton from the endophytic fungus Colletotrichum gloeosporioides MT-51 of Huperzia serrata","authors":"Bei-Bei Zhang ,&nbsp;Hong-Yun Yang ,&nbsp;Xiao-Yun Yan ,&nbsp;Na Xiong ,&nbsp;Lin Zhang ,&nbsp;Xiao Liu ,&nbsp;Pei-Cheng Zhang ,&nbsp;She-Po Shi ,&nbsp;Xu Zhang ,&nbsp;Juan Wang","doi":"10.1016/j.tetlet.2025.155691","DOIUrl":"10.1016/j.tetlet.2025.155691","url":null,"abstract":"<div><div>A hepatoprotective decalin-tetramic acid derivative colletotrichalasin A (<strong>1</strong>) which possesses a unique pentacyclic 6/6/5/6/5 fused ring system was isolated from the endophytic fungus <em>Colletotrichum gloeosporioides</em> MT-51 of <em>Huperzia serrata</em>. Besides, three known alkaloids (<strong>2–4</strong>) were also obtained. Their planar structures were established through integrative NMR, UV, IR, and HRESIMS spectroscopic analysis. The absolute configuration of compound <strong>1</strong> was determined using GIAO <sup>13</sup>C NMR DP4+ analysis and electronic circular dichroism (ECD) calculations. Compound <strong>1</strong> exhibited significant hepatoprotective activity with 74.6 % cell viability (<em>p</em> &lt; 0.0001) at a concentration of 10 μM. A plausible biosynthetic pathway for <strong>1</strong> was proposed based on its PK-NRP hybrid scaffold.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155691"},"PeriodicalIF":1.5,"publicationDate":"2025-06-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144231948","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
Photomodulation of intramolecular hydrogen bonding in azobenzene-derived imines 偶氮苯衍生亚胺分子内氢键的光电调节
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-06-03 DOI: 10.1016/j.tetlet.2025.155686
Huiping Wu, Jingwen Zhang, Chengxi Zhao, Fei Tong, Ruirui Gu
{"title":"Photomodulation of intramolecular hydrogen bonding in azobenzene-derived imines","authors":"Huiping Wu,&nbsp;Jingwen Zhang,&nbsp;Chengxi Zhao,&nbsp;Fei Tong,&nbsp;Ruirui Gu","doi":"10.1016/j.tetlet.2025.155686","DOIUrl":"10.1016/j.tetlet.2025.155686","url":null,"abstract":"<div><div>Janus-type azobenzene-derived imines featuring intramolecular hydrogen bonds have been successfully synthesized and characterized. Crystal structures of these imines have been obtained, revealing that two of them exhibit hydrogen bonding at the azo‑nitrogen, which can be switched to the imine nitrogen following photo-induced conformational flipping of the azobenzene unit. This switching behavior holds significant promise for the design of photo-responsive constitutional dynamic imine libraries.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155686"},"PeriodicalIF":1.5,"publicationDate":"2025-06-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144222078","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
Aromatic sulfonation with sulfur dioxide via Trifluoroacetylsulfuric acid 用三氟乙酰硫酸与二氧化硫进行芳香磺化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-30 DOI: 10.1016/j.tetlet.2025.155677
Jen-Chieh Wang, Sungah Kim, Joo Ho Lee, Carlos Ascencio, Kyung Woon Jung
{"title":"Aromatic sulfonation with sulfur dioxide via Trifluoroacetylsulfuric acid","authors":"Jen-Chieh Wang,&nbsp;Sungah Kim,&nbsp;Joo Ho Lee,&nbsp;Carlos Ascencio,&nbsp;Kyung Woon Jung","doi":"10.1016/j.tetlet.2025.155677","DOIUrl":"10.1016/j.tetlet.2025.155677","url":null,"abstract":"<div><div>We report the regioselective sulfonation of aromatic compounds using SO<sub>2</sub> and O<sub>2</sub> with catalytic H<sub>2</sub>O<sub>2</sub> in TFAOH/TFAA via a one-pot two-step sequence, affording arylsulfonic acids in good to excellent yields. In the first step, the reactive sulfonating intermediate, TFAOSO<sub>3</sub>H (<strong>1</strong>), is generated in situ, which then efficiently sulfonated the aromatic compounds in the second step. Regioselectivity of the reaction follows general electrophilic aromatic substitution (EAS) trends, where mesomeric and inductive effects of substituents dictate the sulfonation position. Compared to conventional methods in aromatic sulfonation using SO<sub>3</sub> and oleum, this approach provides milder reaction conditions, easier isolation of the sulfonated products, and improved step economy, offering a cost-effective route to access arylsulfonic acids.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155677"},"PeriodicalIF":1.5,"publicationDate":"2025-05-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144195043","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
Regioretention probes distinguish ring scission mechanisms in nitrogen insertion reactions 区域保留探针区分氮插入反应中的环断裂机制
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-29 DOI: 10.1016/j.tetlet.2025.155684
Yahia Ali, Liao Chen, Mark D. Levin
{"title":"Regioretention probes distinguish ring scission mechanisms in nitrogen insertion reactions","authors":"Yahia Ali,&nbsp;Liao Chen,&nbsp;Mark D. Levin","doi":"10.1016/j.tetlet.2025.155684","DOIUrl":"10.1016/j.tetlet.2025.155684","url":null,"abstract":"<div><div>Atom insertion reactions into ring systems may occur via one of two pathways, proceeding either through initial cyclization to form a 3-membered ring intermediate followed by cleavage of the ring-fusion bond, or through initial ring-scission followed by recyclization onto the inserting atom. Herein, we demonstrate the use of regioretention probes, substrates with latent symmetry that is unveiled only in the case of ring scission and are thus able to distinguish between possible mechanisms for atom insertion. We apply these probes to three previously reported nitrogen insertion methods and in each case unambiguously establish whether the reaction proceeds through aziridination or C<img>C cleavage. In particular, we show that recently reported cobalt- or manganese-catalyzed nitrogen insertion protocols, postulated to proceed via an aziridinyl radical intermediate, instead proceed through a ring-opened ketone-containing intermediate.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155684"},"PeriodicalIF":1.5,"publicationDate":"2025-05-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144204797","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
Base-promoted efficient transformation of aryl methylene bromides and DMSO to vinyl sulfoxides 碱促进芳基亚甲基溴和二甲基亚砜高效转化为乙烯基亚砜
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-29 DOI: 10.1016/j.tetlet.2025.155667
Aiguo Gu , Xiaofan Shi , Junhai Huang , Rongkang Zhang , Liliang Huang , Huangdi Feng
{"title":"Base-promoted efficient transformation of aryl methylene bromides and DMSO to vinyl sulfoxides","authors":"Aiguo Gu ,&nbsp;Xiaofan Shi ,&nbsp;Junhai Huang ,&nbsp;Rongkang Zhang ,&nbsp;Liliang Huang ,&nbsp;Huangdi Feng","doi":"10.1016/j.tetlet.2025.155667","DOIUrl":"10.1016/j.tetlet.2025.155667","url":null,"abstract":"<div><div>Sulfoxides and their derivatives have attracted considerable attention due to their extensive applications in both medicinal and organic chemistry, serving as versatile chiral auxiliaries or ligands in transition-metal catalysis and as fundamental building blocks in organic synthesis. Herein, we report the development of an efficient tandem reaction for the chemoselective synthesis of vinyl sulfoxides from aryl methylene bromides and DMSO, which serves simultaneously as an oxidant, substrate, and solvent. This innovative method involves sequential Kornblum oxidation of bromide compounds to produce the corresponding aldehydes, which subsequently undergo base-promoted condensation with DMSO. The reaction shows remarkable tolerance for a variety of functional groups on the phenyl ring, and notably, 2-(bromomethyl)naphthalene is also shown to be a compatible substrate, further extending the scope of this methodology.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155667"},"PeriodicalIF":1.5,"publicationDate":"2025-05-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144195042","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
Studies toward the synthesis of strasseriolide A & B via a ring-closing metathesis strategy 闭环复合策略合成strasseriolide A和B的研究
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-29 DOI: 10.1016/j.tetlet.2025.155669
Bashweshawar S. Dhulshette , Shikha Mittal , Subhash Ghosh
{"title":"Studies toward the synthesis of strasseriolide A & B via a ring-closing metathesis strategy","authors":"Bashweshawar S. Dhulshette ,&nbsp;Shikha Mittal ,&nbsp;Subhash Ghosh","doi":"10.1016/j.tetlet.2025.155669","DOIUrl":"10.1016/j.tetlet.2025.155669","url":null,"abstract":"<div><div>This communication describes a synthetic approach for strasseriolide A &amp; B via ring-closing metathesis reaction. The stereoselective synthesis of key olefin fragments, followed by their assembly, yielded the crucial bis-olefinic intermediate. However, despite our best efforts, the critical ring-closing metathesis reaction was unsuccessful.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155669"},"PeriodicalIF":1.5,"publicationDate":"2025-05-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144184984","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 progress in direct dithiocarbamation reactions involving simple electrophiles: Strategies, mechanisms and future prospects 涉及简单亲电试剂的直接二硫代氨基甲酸反应的最新进展：策略、机制和未来展望
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-28 DOI: 10.1016/j.tetlet.2025.155680
Nitin Kumar , Shweta Singh
{"title":"Recent progress in direct dithiocarbamation reactions involving simple electrophiles: Strategies, mechanisms and future prospects","authors":"Nitin Kumar ,&nbsp;Shweta Singh","doi":"10.1016/j.tetlet.2025.155680","DOIUrl":"10.1016/j.tetlet.2025.155680","url":null,"abstract":"<div><div>Dithiocarbamates (DTCs) are identified as a type of chemical entities marked by the presence of the dithiocarbamate functional group (amine-1-carbodithioic acid -amides originating from dithiocarbamic acid), where a carbon atom is linked covalently to two sulfur atoms and a nitrogen atom. These compounds constitute a versatile organo‑sulfur system, which has been the subject of extensive research over the past two decades, particularly regarding their synthetic and pharmacological applications. The properties associated with DTCs, their derivatives, and the related metal complexes encompass antitumor, antiviral, anti-HIV, antibacterial, antitubercular, antifungal, antimicrobial, and antioxidant features.</div><div>This review article presents a detailed analysis of recent progress in direct dithiocarbamation reactions, classifying them based on various sources of the –S–C(<em>S</em>)NR<sub>2</sub> group. It highlights the substrate scope and reaction mechanisms while also addressing certain synthetic limitations and practical applications. Aimed at both general readers and experts, this review seeks to provide up-to-date insights into the field, fostering new ideas for organosulfur compound synthesis.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155680"},"PeriodicalIF":1.5,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144204793","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 enol silane formation-alkylation reactions of ketones promoted by trimethylsilyl trifluoromethanesulfonate: Direct access to β,β-diarylated ketones and related compounds 一锅烯醇硅烷生成-三甲基硅基三氟甲烷磺酸促进酮类的烷基化反应：直接获得β、β-二芳化酮类及相关化合物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-28 DOI: 10.1016/j.tetlet.2025.155679
Katelyn A. Marchione, Karmen M. Smith, C. Wade Downey
{"title":"One-pot enol silane formation-alkylation reactions of ketones promoted by trimethylsilyl trifluoromethanesulfonate: Direct access to β,β-diarylated ketones and related compounds","authors":"Katelyn A. Marchione,&nbsp;Karmen M. Smith,&nbsp;C. Wade Downey","doi":"10.1016/j.tetlet.2025.155679","DOIUrl":"10.1016/j.tetlet.2025.155679","url":null,"abstract":"<div><div>Ketones undergo enol silane formation and subsequent alkylation in a single reaction flask when treated with an amine base, a secondary alkyl acetate, and trimethylsilyl trifluoromethanesulfonate (TMSOTf). The reaction appears to be general to a wide range of alkyl and aryl ketones as well as ester, thioester, amide, and aldehyde pronucleophiles. Diarylmethyl acetates are ideal electrophiles, as are certain monoarylmethyl acetates, undergoing ionization to form secondary carbocations in the presence of TMSOTf. These reactions occur under mild conditions with exceptional efficiency, including 15 examples over 90 % yield.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"168 ","pages":"Article 155679"},"PeriodicalIF":1.5,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144222077","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
Iron-catalyzed Glycal cis-Aminoacyloxylation for 2-amino saccharide synthesis 铁催化糖基顺式氨基酰基化合成2-氨基糖
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-28 DOI: 10.1016/j.tetlet.2025.155678
Le Yin , Dakang Zhang , Zixiang Jiang, Pinzhi Wang, Joseph C. Levine, Dylan L. Labbe, Hao Xu
{"title":"Iron-catalyzed Glycal cis-Aminoacyloxylation for 2-amino saccharide synthesis","authors":"Le Yin ,&nbsp;Dakang Zhang ,&nbsp;Zixiang Jiang,&nbsp;Pinzhi Wang,&nbsp;Joseph C. Levine,&nbsp;Dylan L. Labbe,&nbsp;Hao Xu","doi":"10.1016/j.tetlet.2025.155678","DOIUrl":"10.1016/j.tetlet.2025.155678","url":null,"abstract":"<div><div>We report here a new catalytic and exclusively 1,2-<em>cis</em>-selective glycal aminoacyloxylation method for 2-amino saccharide synthesis. This iron-catalyzed glycosylation is effective for a wide variety of glycosyl donors with consistently high stereoselectivity and excellent functional-group compatibility, which facilitates late-stage amino group incorporation for complex-carbohydrate synthesis.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155678"},"PeriodicalIF":1.5,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144190299","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
Photoredox catalysis enabled selective CN bond cleavage in ring-strained tertiary amines 光氧化还原催化使环应变叔胺的CN键选择性裂解
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-23 DOI: 10.1016/j.tetlet.2025.155666
Yu Zhou, Pu-Sheng Wang
{"title":"Photoredox catalysis enabled selective CN bond cleavage in ring-strained tertiary amines","authors":"Yu Zhou,&nbsp;Pu-Sheng Wang","doi":"10.1016/j.tetlet.2025.155666","DOIUrl":"10.1016/j.tetlet.2025.155666","url":null,"abstract":"<div><div>The selective cleavage of C<img>N bonds in tertiary amines to form secondary amines is a promising strategy for constructing diverse nitrogen-containing compounds. Herein, we introduce a simple method for the selective <em>N</em>-dealkylation of ring-strained tertiary amines under blue LED light irradiation using 4CzIPN as photocatalyst and CCl<sub>4</sub> as oxidant with up to 99% yield.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155666"},"PeriodicalIF":1.5,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144154496","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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