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Efficient one-pot synthesis of bis-benzothiazoles from dicarboxylic acids: A metal-free benzotriazole strategy 二羧酸一锅高效合成双苯并噻唑：无金属苯并三唑策略
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-19 DOI: 10.1016/j.tet.2025.135113
Riham M. Bokhtia , Tejas Srinivasan , Mandy Green , Rajeev Shakuja , Siva S. Panda
{"title":"Efficient one-pot synthesis of bis-benzothiazoles from dicarboxylic acids: A metal-free benzotriazole strategy","authors":"Riham M. Bokhtia ,&nbsp;Tejas Srinivasan ,&nbsp;Mandy Green ,&nbsp;Rajeev Shakuja ,&nbsp;Siva S. Panda","doi":"10.1016/j.tet.2025.135113","DOIUrl":"10.1016/j.tet.2025.135113","url":null,"abstract":"<div><div>We report a green, metal-free, and efficient synthetic protocol for the preparation of bis-benzothiazoles via benzotriazole-mediated activation of dicarboxylic acids. This methodology employs N-acylbenzotriazole intermediates, which react with 2-aminothiophenol under mild conditions in acetic acid to afford the target bis-benzothiazoles in excellent yields. The process avoids the use of toxic reagents, metal catalysts, and harsh conditions, offering a sustainable alternative to conventional methods. Density functional theory (DFT) calculations provide mechanistic insights and thermodynamic profiles, highlighting the role of substituent effects and noncovalent interactions in product stability. The protocol demonstrates broad substrate scope, operational simplicity, and high atom economy, making it a valuable contribution to green heterocyclic synthesis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135113"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145838231","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Blue TADF fluorescence emitter with AIE property and narrow emission in OLED applications 具有AIE特性和窄发射的蓝色TADF荧光发射器在OLED中的应用
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-23 DOI: 10.1016/j.tet.2025.135109
Xiaoling Niu , Wenlong Qu , Haoyu Ma , Tiantian Ma , Zhen Feng , Shengbo Zhu
{"title":"Blue TADF fluorescence emitter with AIE property and narrow emission in OLED applications","authors":"Xiaoling Niu ,&nbsp;Wenlong Qu ,&nbsp;Haoyu Ma ,&nbsp;Tiantian Ma ,&nbsp;Zhen Feng ,&nbsp;Shengbo Zhu","doi":"10.1016/j.tet.2025.135109","DOIUrl":"10.1016/j.tet.2025.135109","url":null,"abstract":"<div><div>Obtaining blue fluorescence emission, easy synthesis, excellent color purity, non-doped emitters has drawn great interest in the application of organic light emitting diodes (OLEDs). Thermally activated delayed fluorescence (TADF) and aggregation-induced emission (AIE) are two promising performance to realize high-efficiency and non-doped OLEDs. Herein, a blue fluorescence emitter of Cz-Trz-CN is designed and synthesized using carbazole derivative as a donor unit and triazine derivative as an acceptor unit by one-step reaction. It exhibits obvious AIE and TADF properties, and narrow emission in OLED applications. The photophysical experiments and the density functional theory (DFT) and time-DFT theoretical studies were used to confirm the AIE and TADF properties of Cz-Trz-CN. The OLEDs performances based on Cz-Trz-CN (nondoped), (doped as guest), and (doped as host) were studied systematically, which exhibited blue emission with CIE coordinates (0.1282, 0.0818), (0.1327, 0.0633) and (0.1249, 0.1135), respectively, and narrow full width at half maximum (FWHM) of 22.0 nm, 21.0 nm and 20.6 nm, respectively. The results show that the AIE and TADF properties are attribute to the highly twisted molecular conformation. This study provide a new method for developing high efficiency, color purity and non-doped OLED emitters.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135109"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145838237","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 3-benzoylisoxazolines by copper(Ⅰ) bromide-catalyzed 1,3-dipolar cycloaddition of nitroketones with dipolarophiles 溴化铜（Ⅰ）催化硝基酮与亲偶极试剂1,3-偶极环加成合成3-苯甲酰异恶唑啉
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-11 DOI: 10.1016/j.tet.2025.135088
Xiaoyu Liao , Zhiyun Zhao , Jiyi Lv , Xiling Deng , Xinrun Zhao , Yangzi Chen , Wei Zhang , Pinghua Sun , Xinhui Pan
{"title":"Synthesis of 3-benzoylisoxazolines by copper(Ⅰ) bromide-catalyzed 1,3-dipolar cycloaddition of nitroketones with dipolarophiles","authors":"Xiaoyu Liao ,&nbsp;Zhiyun Zhao ,&nbsp;Jiyi Lv ,&nbsp;Xiling Deng ,&nbsp;Xinrun Zhao ,&nbsp;Yangzi Chen ,&nbsp;Wei Zhang ,&nbsp;Pinghua Sun ,&nbsp;Xinhui Pan","doi":"10.1016/j.tet.2025.135088","DOIUrl":"10.1016/j.tet.2025.135088","url":null,"abstract":"<div><div>An efficient copper(Ⅰ) bromide catalyzed 1,3-dipolar cycloaddition reaction of different α-nitroketones with dipolarophiles has been investigated. These reactions afford the corresponding 3-benzoylisoxazolines in moderate to high yields (up to 99.9 %) under mild conditions. This method provides an economical and simple route to construction of isoxazole or isoxazoline ring.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135088"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145838303","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Steroidal saponins from Paris polyphylla var. yunnanensis and their application in antibacterial preservation 云南白杨甾体皂苷及其在抗菌保鲜中的应用
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-18 DOI: 10.1016/j.tet.2025.135111
Yu Zhang , Yu-Chen Zhang , Chen-Sen Xu , Yu-Chen Fan , Jing Zhang , Chao Wang , Hao-Lin Yu , Jin-Zhong Hu , Zhi-Xin Liao
{"title":"Steroidal saponins from Paris polyphylla var. yunnanensis and their application in antibacterial preservation","authors":"Yu Zhang ,&nbsp;Yu-Chen Zhang ,&nbsp;Chen-Sen Xu ,&nbsp;Yu-Chen Fan ,&nbsp;Jing Zhang ,&nbsp;Chao Wang ,&nbsp;Hao-Lin Yu ,&nbsp;Jin-Zhong Hu ,&nbsp;Zhi-Xin Liao","doi":"10.1016/j.tet.2025.135111","DOIUrl":"10.1016/j.tet.2025.135111","url":null,"abstract":"<div><div>Three previously undescribed steroidal saponins, polypharycosides A–C (<strong>1</strong>–<strong>3</strong>), along with eight known analogues (<strong>4</strong>–<strong>11</strong>), were isolated from the rhizomes of <em>Paris polyphylla</em> var. <em>yunnanensis</em>. The structures of the previously undescribed compounds were elucidated through comprehensive analysis using 1D/2D NMR spectroscopy, HR-ESI-MS, as well as GC analysis after acid hydrolysis and ECD calculations. the crude steroidal saponin extract showed potent activity against <em>Salmonella typhimurium</em> (MIC = 1 μg/mL, MBC = 8 μg/mL). In vitro antibacterial assays revealed that the extract formed distinct inhibition zones, significantly reduced bacterial ATP levels, and induced protein and nucleic acid leakage from cells, suggesting its antimicrobial mechanism may involve disruption of cell membrane integrity. Furthermore, in a lettuce infection model, the crude steroidal saponin extract effectively inhibited bacterial colonization, with its bactericidal effects exhibiting both dose- and time-dependent dynamics. This study provides a crucial theoretical foundation for the development of novel plant-derived antibacterial agents targeting <em>S. typhimurium.</em></div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135111"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145838236","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 application of CuAAC for the covalent immobilization of homogeneous catalysts, a decade of progress CuAAC在均相催化剂共价固定化中的应用进展，十年来的进展
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-18 DOI: 10.1016/j.tet.2025.135108
Antony E. Fernandes , Olivier Riant , Alain M. Jonas
{"title":"Recent advances in the application of CuAAC for the covalent immobilization of homogeneous catalysts, a decade of progress","authors":"Antony E. Fernandes ,&nbsp;Olivier Riant ,&nbsp;Alain M. Jonas","doi":"10.1016/j.tet.2025.135108","DOIUrl":"10.1016/j.tet.2025.135108","url":null,"abstract":"<div><div>The immobilization of homogeneous catalysts has become a central strategy in the design of efficient and sustainable catalytic systems. By anchoring well-defined molecular catalysts onto soluble or insoluble supports, it is possible to combine the high activity and selectivity of homogeneous catalysis with the operational benefits of heterogeneous systems, including ease of recovery, recyclability, and implementation within continuous flow processes. Among the various approaches to covalent immobilization, the copper-catalyzed azide-alkyne cycloaddition (CuAAC) stands out as a particularly versatile and reliable method. This “click” reaction offers exceptional robustness, functional group tolerance, and modularity, allowing for the immobilization of a broad range of catalytic species — organic and organometallic — under mild conditions. In this article, we update our review published in 2014 and highlight recent advances in the use of CuAAC for catalyst immobilization, from simple single-site catalysts to elaborate multicatalytic systems, including organometallic, organic and multifunctional catalysts, and photocatalysts. We also discuss how the triazole linkage itself can serve not only as a passive tether but also as a functional component, influencing the microenvironment and coordination behavior of the resulting materials. Despite its many strengths, CuAAC is not without limitations, such as the requirement for copper catalyst and potential interference of the triazole unit. These drawbacks are considered in the context of emerging complementary “click” immobilization strategies. Overall, CuAAC remains a cornerstone technology in the immobilization toolbox, offering a powerful platform for building next-generation supported catalysts that approach the performance of their homogeneous counterparts while enabling scalable and sustainable chemical processes.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135108"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145838235","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Sesquiterpenes from Schisandra chinensis: Structural characterization and revision 五味子倍半萜类化合物的结构表征及修订
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-19 DOI: 10.1016/j.tet.2025.135097
Li-Qin Huang , Mei-Fen Bao , Ping Zhang , Xin Yue , Yang Yu
{"title":"Sesquiterpenes from Schisandra chinensis: Structural characterization and revision","authors":"Li-Qin Huang ,&nbsp;Mei-Fen Bao ,&nbsp;Ping Zhang ,&nbsp;Xin Yue ,&nbsp;Yang Yu","doi":"10.1016/j.tet.2025.135097","DOIUrl":"10.1016/j.tet.2025.135097","url":null,"abstract":"<div><div>Chemical investigation of the supercritical CO<sub>2</sub> extract from the fruits of <em>Schisandra chinensis</em> resulted in the isolation of four sesquiterpenoids, including a new compound schisandrins A (<strong>1</strong>). The structures of the compounds were fully elucidated through comprehensive NMR and HRESIMS analyses, supported by X-ray crystallography and ECD. The above isolated compounds are classified as cuparane (<strong>1</strong> and <strong>2</strong>) and chamigrane (<strong>3</strong> and <strong>4</strong>) sesquiterpenoids, both derived biosynthetically from bisabolane. Notably, the structure of compound <strong>3</strong>, which had been erroneously reported in the literature as a widdarane-type sesquiterpene, was revised to a chamigrane-type spirocyclic skeleton. This study not only expands the structural diversity of sesquiterpenoids from <em>S. chinensis</em>, but also highlights the essential role of X-ray diffraction in correcting misassignments based solely on NMR data.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135097"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145838234","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 red-emitting molecular rotor fluorescent nucleoside for microenvironment sensing 微环境传感用红发分子转子荧光核苷
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-20 DOI: 10.1016/j.tet.2025.135112
Guoliang Xu , Yixuan Zhao , Hui Wang , Linshu Wang , Junlin Wen , Hui Mei , Xin Ming
{"title":"A red-emitting molecular rotor fluorescent nucleoside for microenvironment sensing","authors":"Guoliang Xu ,&nbsp;Yixuan Zhao ,&nbsp;Hui Wang ,&nbsp;Linshu Wang ,&nbsp;Junlin Wen ,&nbsp;Hui Mei ,&nbsp;Xin Ming","doi":"10.1016/j.tet.2025.135112","DOIUrl":"10.1016/j.tet.2025.135112","url":null,"abstract":"<div><div>Fluorescent nucleoside analogs (FNAs) serve as powerful tools for investigating the structural and dynamic properties of nucleic acids. However, the development of red-emitting molecular rotor-type fluorescent nucleosides has been relatively limited. Here, we present a red-emitting fluorescent nucleoside analog, <sup>HBC</sup>dU, which is based on a <em>trans</em>-stilbene-linked uracil derivative. This analog exhibits a significant red-shifted emission peak at 625 nm in aqueous solution and demonstrates high sensitivity to changes in polarity, pH, and viscosity. Remarkably, when incorporated into single-stranded oligonucleotides, <sup>HBC</sup>dU shows an enhancement in brightness by nearly ten times as opposed to the free nucleoside, independent of the surrounding flanking bases. These characteristics position <sup>HBC</sup>dU as a promising probe for studying nucleic acid microenvironments and protein-nucleic acid interactions.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135112"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145838230","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Cerium(IV)-mediated nitrooxylation-phosphorylation of α-(trifluoromethyl)styrenes with H-phosphonates and H-phosphine oxides 铈（IV）介导的α-（三氟甲基）苯乙烯与h -膦酸盐和h -膦氧化物的硝基氧化磷酸化反应
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-14 DOI: 10.1016/j.tet.2025.135093
Xuxue Zhang , Jiekun Zhu , Junfeng Teng , Chao Zhou , Hao Xu , Xiaolu Yin , Chenxi Li , Xiaoyi Jiang , Song Cao
{"title":"Cerium(IV)-mediated nitrooxylation-phosphorylation of α-(trifluoromethyl)styrenes with H-phosphonates and H-phosphine oxides","authors":"Xuxue Zhang ,&nbsp;Jiekun Zhu ,&nbsp;Junfeng Teng ,&nbsp;Chao Zhou ,&nbsp;Hao Xu ,&nbsp;Xiaolu Yin ,&nbsp;Chenxi Li ,&nbsp;Xiaoyi Jiang ,&nbsp;Song Cao","doi":"10.1016/j.tet.2025.135093","DOIUrl":"10.1016/j.tet.2025.135093","url":null,"abstract":"<div><div>An efficient CAN-mediated nitrooxylation-phosphorylation of α-(trifluoromethyl)styrenes with <em>H</em>-phosphonates and <em>H</em>-phosphine oxides was described. This novel difunctionalization reaction could enable the rapid incorporation of nitrooxy group and phosphoryl group into α-(trifluoromethyl)styrene in one step, affording the β-nitrooxy-β-trifluoromethyl-phosphonates and β-nitrooxy-β-trifluoromethyl-phosphine oxides in moderate to good yields.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135093"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145765751","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Striking difference in nucleophilic substitution in 4,7-dichloro-[1,2,5]oxadiazolo[3,4-d]pyridazine 1-oxide by S-, N- and O-nucleophiles 亲核试剂S-、N-和o-取代4,7-二氯-[1,2,5]恶二唑[3,4-d]吡嗪1-氧化物的亲核性差异
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-18 DOI: 10.1016/j.tet.2025.135094
Timofey N. Chmovzh , Rinat R. Aysin , Egor D. Kotov , Karim S. Gaisin , Darina I. Nasyrova , Oleg A. Rakitin
{"title":"Striking difference in nucleophilic substitution in 4,7-dichloro-[1,2,5]oxadiazolo[3,4-d]pyridazine 1-oxide by S-, N- and O-nucleophiles","authors":"Timofey N. Chmovzh ,&nbsp;Rinat R. Aysin ,&nbsp;Egor D. Kotov ,&nbsp;Karim S. Gaisin ,&nbsp;Darina I. Nasyrova ,&nbsp;Oleg A. Rakitin","doi":"10.1016/j.tet.2025.135094","DOIUrl":"10.1016/j.tet.2025.135094","url":null,"abstract":"<div><div>A study of nucleophilic substitution in 4,7-dichloro[1,2,5]oxadiazolo[3,4-<em>d</em>]pyridazine 1-oxide <strong>4</strong> showed that the nature of the nucleophile has a significant effect on the position and number of substituted chlorine atoms. Treatment of the dichloride <strong>4</strong> with amines resulted in the selective substitution of the chlorine atom at position 4 or of two chlorine atoms, depending on the amount of amine used. The reaction with thiols does not stop at the formation of a mono-substitution product and leads to bis-substitution products regardless of the structure of the thiol, its amount and reaction conditions. The reaction of <strong>4</strong> with alcohols and sodium alcoholates is not regioselective and afforded a mixture of mono-substitution products at positions 4 and 7, while hydrolysis of <strong>4</strong> gave 4-chloro-7-oxo-6,7-dihydro-[1,2,5]oxadiazolo[3,4-<em>d</em>]pyridazine 1-oxide only. The results of DFT calculations of the first and second stages of S<sub>N</sub>Ar substitution reactions showed that the reactivity of the chlorine atoms in positions 4 and 7 does not differ significantly, and the reason for the differences in reactivity is the presence of kinetic control for <em>N</em>-nucleophiles, thermodynamic control for reactions with <em>O</em>-nucleophiles, and muted effects for <em>S</em>-nucleophiles. The position of the oxygen atom of the <em>N</em>-oxide in furoxanopyridazines was rigorously proven by X-ray structural analysis data.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135094"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145789477","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Unified total synthesis of colisporifungin, ophiotine and verruculin 大肠菌素、蛇啡肽和疣状蛋白的统一全合成
IF 2.2 3区 化学
Tetrahedron Pub Date : 2026-04-01 Epub Date: 2025-12-22 DOI: 10.1016/j.tet.2025.135123
Katsuki Akiyama, Kenshu Fujiwara
{"title":"Unified total synthesis of colisporifungin, ophiotine and verruculin","authors":"Katsuki Akiyama,&nbsp;Kenshu Fujiwara","doi":"10.1016/j.tet.2025.135123","DOIUrl":"10.1016/j.tet.2025.135123","url":null,"abstract":"<div><div>The total synthesis of colisporifungin, ophiotine and verruculin, possessing a common cyclic lipohexadepsipeptide framework including three <span>d</span>-amino acids and β-alanine, was successfully achieved by a unified, convergent route based on solution-phase peptide synthesis. The framework was assembled from a tripeptide fragment and a lipotridepsipeptide segment by a connection/cyclization process at the final stage, where a ring-forming condensation between the less-hindered β-alanine and the <span>l</span>-threonine residues effectively occurred. Initial introduction of the fatty acid moiety to <span>d</span>-glutamine to avoid unnecessary protecting group manipulations was also helpful for making the synthesis concise.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"192 ","pages":"Article 135123"},"PeriodicalIF":2.2,"publicationDate":"2026-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145838242","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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