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Selactamyuine A, a new C15N2-type Lycopodium alkaloid from Lycopodium serratum Thunb. var. serratum Selactamyuine A是一种新的c15n2型石蒜生物碱。var. serratum
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-02-01 Epub Date: 2025-11-16 DOI: 10.1016/j.tetlet.2025.155894
Miyuu Sugi , Yusuke Hirasawa , Takefumi Yamashita , Nahoko Uchiyama , Hiroshi Morita
{"title":"Selactamyuine A, a new C15N2-type Lycopodium alkaloid from Lycopodium serratum Thunb. var. serratum","authors":"Miyuu Sugi ,&nbsp;Yusuke Hirasawa ,&nbsp;Takefumi Yamashita ,&nbsp;Nahoko Uchiyama ,&nbsp;Hiroshi Morita","doi":"10.1016/j.tetlet.2025.155894","DOIUrl":"10.1016/j.tetlet.2025.155894","url":null,"abstract":"<div><div>A new <em>Lycopodium</em> alkaloid, selactamyuine A (<strong>1</strong>), isolated from <em>Lycopodium serratum</em> Thunb<em>.</em> var<em>. serratum</em> exhibits a unique C<sub>15</sub>N<sub>2</sub> framework. Selactamyuine A (<strong>1</strong>) consists of a γ-lactam ring and a decahydroquinoline ring with a slowly rotating <em>N</em>-acetyl group, covalently connected through a methylene linker. Its structure and relative configuration were elucidated based on spectroscopic data and <sup>13</sup>C NMR chemical shift calculations, and its absolute configuration was investigated by a combination of CD spectroscopy and TD-DFT calculation.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155894"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145616049","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
Direct access to cyclic diamides via the oxidative Joullié-Ugi reaction 通过氧化joulli<s:1> - ugi反应直接获得环二胺
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-02-01 Epub Date: 2025-11-21 DOI: 10.1016/j.tetlet.2025.155903
Jing Li, Mengyu Gao, Jinyu Zhang
{"title":"Direct access to cyclic diamides via the oxidative Joullié-Ugi reaction","authors":"Jing Li,&nbsp;Mengyu Gao,&nbsp;Jinyu Zhang","doi":"10.1016/j.tetlet.2025.155903","DOIUrl":"10.1016/j.tetlet.2025.155903","url":null,"abstract":"<div><div>A PhI(OAc)₂-mediated oxidative Joullié-Ugi reaction of amino acids has been developed. This method enables efficient bisamide synthesis via amino acid decarboxylation and subsequent trapping of the iminium intermediate with aryl isocyanides. Conducted in TFE at room temperature, it exhibits a broad scope for isocyanides, delivering products in high yields, as demonstrated on a gram scale.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155903"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145555291","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
Aqueous-phase construction of dihydroxy lactam via cascade reaction catalyzed by amino acid salts 氨基酸盐催化级联反应构建二羟基内酰胺的水相
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-02-01 Epub Date: 2025-12-06 DOI: 10.1016/j.tetlet.2025.155923
Bingbing Hou , Shengnan Zhang , Jiajing Su , Fangyi Gong , Wenke Sun , Longjun Ma , Hongxin Liu
{"title":"Aqueous-phase construction of dihydroxy lactam via cascade reaction catalyzed by amino acid salts","authors":"Bingbing Hou ,&nbsp;Shengnan Zhang ,&nbsp;Jiajing Su ,&nbsp;Fangyi Gong ,&nbsp;Wenke Sun ,&nbsp;Longjun Ma ,&nbsp;Hongxin Liu","doi":"10.1016/j.tetlet.2025.155923","DOIUrl":"10.1016/j.tetlet.2025.155923","url":null,"abstract":"<div><div>Herein, we have developed a novel, environmentally friendly, straightforward, and practical methodology for the construction of 1,3-dihydroxy lactams incorporating multiple quaternary carbon centers through cascade reactions between ketoamides and acetyl compounds in aqueous media. Such molecular architectures are prevalent in natural product systems. This transformation constitutes the first reported instance of employing an amino acid salt to catalyze the formation of dihydroxy lactam-fused polycyclic quaternary carbon frameworks <em>via</em> a sequential aldol and azo-aldol addition cascade process in an aqueous environment. Notably, this reaction exhibits exceptional atom economy, facilitates gram-scale synthesis, and enables multiple catalytic turnovers, delivering the desired products in excellent yields and diastereoselectivities with convenient isolation <em>via</em> centrifugation.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155923"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145733303","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
Polystyrene-supported N-prolyl tetrapeptides catalyzed asymmetric Michael addition of aldehydes to nitroolefins 聚苯乙烯负载的n -丙基四肽催化非对称Michael加成醛到硝基烯烃
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-02-01 Epub Date: 2025-11-24 DOI: 10.1016/j.tetlet.2025.155908
Meng Yuan , Tian-Rui Lian , Tie-Ying Ding, Yang-Xing Liu, Chao-Shan Da
{"title":"Polystyrene-supported N-prolyl tetrapeptides catalyzed asymmetric Michael addition of aldehydes to nitroolefins","authors":"Meng Yuan ,&nbsp;Tian-Rui Lian ,&nbsp;Tie-Ying Ding,&nbsp;Yang-Xing Liu,&nbsp;Chao-Shan Da","doi":"10.1016/j.tetlet.2025.155908","DOIUrl":"10.1016/j.tetlet.2025.155908","url":null,"abstract":"<div><div>The polystyrene-supported <em>N</em>-prolyl tetrapeptide was disclosed to catalyze the asymmetric addition of aldehydes to nitroolefins with water as solvent, achieving high yields, good enantioselectivities, and excellent diastereoselectivities. The heterogeneous catalyst can be successfully recovered and reused at least five times without loss of stereoselectivity. The results demonstrated that the configuration of the Michael adduct depends on both the configuration of the <em>N</em>-terminal amino acid and whether the <em>N</em>-terminal residue is a prolyl residue or a primary amino acid. The secondary structure of the catalyst is also seriously responsible for the direction of the asymmetric induction.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"175 ","pages":"Article 155908"},"PeriodicalIF":1.5,"publicationDate":"2026-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145616503","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
Gram-scale synthesis of the thiazolidinedione-based mitoNEET ligand NL-1 using a Hantzsch ester reduction 用Hantzsch酯还原法合成以噻唑烷二酮为基础的mitoNEET配体NL-1
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-10-18 DOI: 10.1016/j.tetlet.2025.155863
James Mersch , Yehenew Agazie , Michael A. Menze , Mary E. Konkle , Jason D. Huber , Werner J. Geldenhuys
{"title":"Gram-scale synthesis of the thiazolidinedione-based mitoNEET ligand NL-1 using a Hantzsch ester reduction","authors":"James Mersch ,&nbsp;Yehenew Agazie ,&nbsp;Michael A. Menze ,&nbsp;Mary E. Konkle ,&nbsp;Jason D. Huber ,&nbsp;Werner J. Geldenhuys","doi":"10.1016/j.tetlet.2025.155863","DOIUrl":"10.1016/j.tetlet.2025.155863","url":null,"abstract":"<div><div>MitoNEET (CISD1), an [2Fe-2S] cluster protein located on the outer mitochondrial membrane and known for its role in cellular redox regulation and bioenergetics, has been identified as a novel ferroptosis-related drug target in neurodegeneration and cancer. The mitoNEET ligand NEET ligand-1 (NL-1) was developed as a pharmacological tool to elucidate the biochemistry of the novel protein in a variety of disease states, ranging from oncology to neurodegenerative disorders. Here, we present a scalable gram-level synthesis of the thiazolidinedione (TZD) containing NL-1 from the precursor CI-987 using the Hantzsch ester reduction as an alternative to conventional lithium borohydride or cobalt chloride-based methods. This optimized protocol enables the reliable production of NL-1 in quantities sufficient for preclinical disease modeling.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155863"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145361383","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
Enantioselective reductive hydrosilylation of imines using HSiCl3 with a trace of bifunctional chiral pyridine N-oxide organocatalyst bearing a urea hydrogen-bond donor 用含尿素氢键供体的微量双功能手性吡啶n-氧化物有机催化剂HSiCl3对亚胺的对映选择性硅氢化反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-11-14 DOI: 10.1016/j.tetlet.2025.155901
Gakushi Morita, Hinoki Sakamura, Yusuke Fukushima, Michimasa Hayashi, Tetsuya Fujimoto
{"title":"Enantioselective reductive hydrosilylation of imines using HSiCl3 with a trace of bifunctional chiral pyridine N-oxide organocatalyst bearing a urea hydrogen-bond donor","authors":"Gakushi Morita,&nbsp;Hinoki Sakamura,&nbsp;Yusuke Fukushima,&nbsp;Michimasa Hayashi,&nbsp;Tetsuya Fujimoto","doi":"10.1016/j.tetlet.2025.155901","DOIUrl":"10.1016/j.tetlet.2025.155901","url":null,"abstract":"<div><div>Novel chiral organocatalysts (<strong>3a-e</strong>), in which both pyridine <em>N</em>-oxide and urea functional groups are bonded to a chiral aminoindanol scaffold, were designed for the enantioselective hydrosilylation of imines using HSiCl<sub>3</sub>. The reactions of the imines with HSiCl<sub>3</sub> in the presence of the bifunctional organocatalysts proceeded effectively, and the corresponding chiral amines were obtained with up to 98 % ee using only 0.1 mol% catalyst loading of <strong>3e</strong>.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155901"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145576483","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
Step-wise flow synthesis of l-ascorbic acid from L-sorbose l-山梨糖分步流动合成l-抗坏血酸
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-10-28 DOI: 10.1016/j.tetlet.2025.155851
Maduabuchi Angus Modum , Stefan Smulik , James W. Kim , Andrea Gorrell , Kalindi D. Morgan
{"title":"Step-wise flow synthesis of l-ascorbic acid from L-sorbose","authors":"Maduabuchi Angus Modum ,&nbsp;Stefan Smulik ,&nbsp;James W. Kim ,&nbsp;Andrea Gorrell ,&nbsp;Kalindi D. Morgan","doi":"10.1016/j.tetlet.2025.155851","DOIUrl":"10.1016/j.tetlet.2025.155851","url":null,"abstract":"<div><div>Transformation of L-sorbose via sequential acetonide protection, oxidation, and lactonization is a pivotal route towards vitamin C synthesis, yet traditional batch and large fermentation processes have not been radically re-imagined in decades. Herein, we report a step-wise flow platform that accomplishes three key transformations of L-sorbose in minutes with high yields and minimal purification. In the first module, L-sorbose undergoes diacetonide protection in a PTFE coil reactor at 0–5 °C, reaching 95 % (crude) conversion in 30 min. The protected sugar is then oxidized inline to the corresponding 2-keto-L-gluconic acid with final direct lactonization to <span>l</span>-ascorbic acid. Thus, under current conditions, the total conversion of L-sorbose to Vitamin C is achieved in 90 total minutes with 85 % crude Vitamin C yield and 57 % pure Vitamin C yield.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155851"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145414308","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
Benzindole-based donor-acceptor-donor ratiometric-type fluorescent probe for hydrazine 基于苯并吲哚的供-受体-供-供比例型联氨荧光探针
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-10-25 DOI: 10.1016/j.tetlet.2025.155873
Guiqin Yu , Xuming Liu , Yan Ming , Bei Wang, Xiang Liu
{"title":"Benzindole-based donor-acceptor-donor ratiometric-type fluorescent probe for hydrazine","authors":"Guiqin Yu ,&nbsp;Xuming Liu ,&nbsp;Yan Ming ,&nbsp;Bei Wang,&nbsp;Xiang Liu","doi":"10.1016/j.tetlet.2025.155873","DOIUrl":"10.1016/j.tetlet.2025.155873","url":null,"abstract":"<div><div>A novel benzindole-based donor–acceptor–donor (D–A–D) fluorescent probe (HST) has been rationally designed and synthesized for the highly selective and sensitive detection of hydrazine (N₂H₄). The sensing mechanism is based on the hydrazine-triggered nucleophilic addition to the conjugated double bond, which disrupts the intramolecular charge transfer (ICT) process, resulting in significant fluorescence quenching. HST demonstrates remarkable features including a large Stokes shift (136 nm), rapid response within 3 min, excellent selectivity, and a low detection limit (3.47 μM). Furthermore, HST enables direct, naked-eye recognition of hydrazine under both visible and UV light. These findings suggest HST as a promising tool for practical applications in environmental and biological hydrazine monitoring.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155873"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145361388","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
A novel synthetic route to a process-related impurity of alectinib 一种新的合成途径来获得与alectinib工艺相关的杂质
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-10-21 DOI: 10.1016/j.tetlet.2025.155869
Sai Zhao , Lijuan Zhu , Nian Tong , Qi Qi
{"title":"A novel synthetic route to a process-related impurity of alectinib","authors":"Sai Zhao ,&nbsp;Lijuan Zhu ,&nbsp;Nian Tong ,&nbsp;Qi Qi","doi":"10.1016/j.tetlet.2025.155869","DOIUrl":"10.1016/j.tetlet.2025.155869","url":null,"abstract":"<div><div>A novel synthetic route has been developed for the preparation of a key drug impurity of alectinib, a highly potent ALK inhibitor used in the treatment of non-small cell lung cancer. This impurity, designated as compound <strong>1</strong> and chemically identified as 9-ethyl-6,6-dimethyl-8-[4-(1,4-oxazinan-4-yl)hexahydropyridin-1-yl]-11-oxo-6,11-dihydrobenzo[<em>d</em>]naphtho[3,2-b]furan-3‑carbonitrile, originates from the initial cyclization step in the synthetic procedure of alectinib. In comparison to the method described in the patent, the new route offers several advantages, including higher yields, reduced Pd catalyst loading, and enhanced sustainability. This approach is expected to contribute significantly to the advancement of process chemistry and to improved quality control in the manufacture of alectinib.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155869"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145414307","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
Direct synthesis of sulfonyl azides from thiols and sodium azide: a one-pot sequential approach utilizing TCCA as an oxidizing and chlorinating agent 由硫醇和叠氮化钠直接合成磺酰叠氮化物：利用三聚氰胺作为氧化和氯化剂的一锅序贯方法
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2026-01-15 Epub Date: 2025-11-17 DOI: 10.1016/j.tetlet.2025.155897
Fateh Golmoradi , Masoumeh Foroutan Koudehi , Hossein Fasihi Dastjerdi , Farzad Nikpour , Ramin Zibaseresht
{"title":"Direct synthesis of sulfonyl azides from thiols and sodium azide: a one-pot sequential approach utilizing TCCA as an oxidizing and chlorinating agent","authors":"Fateh Golmoradi ,&nbsp;Masoumeh Foroutan Koudehi ,&nbsp;Hossein Fasihi Dastjerdi ,&nbsp;Farzad Nikpour ,&nbsp;Ramin Zibaseresht","doi":"10.1016/j.tetlet.2025.155897","DOIUrl":"10.1016/j.tetlet.2025.155897","url":null,"abstract":"<div><div>A concise and efficient one-pot two-step sequential synthesis of sulfonyl azides from readily available thiols has been developed. This method involves an initial reaction of the thiol with TCCA in 96 % ethanol to generate the corresponding sulfonyl chloride. Subsequently, an aqueous solution of sodium azide is added to the reaction mixture, leading to the formation of the desired sulfonyl azide. Utilizing TCCA as a dual oxidant and chlorinating agent, this novel approach enables the direct conversion of thiols to sulfonyl azides in good to high yields (70–93 %) at room temperature. This streamlined approach provides facile access to a diverse array of sulfonyl azide derivatives.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"174 ","pages":"Article 155897"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145576485","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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