Pub Date : 2025-01-31DOI: 10.1016/j.tet.2025.134519
Chao Kan , Chongxun Ge , Song Liu , Song Shi , Hu He , Weike Su
The potential of PARG, the most active dePARylation enzyme, as a therapeutic target lies in its synthetic lethal relationship with other DNA repair genes. The development of PARG inhibitors represents a significant advancement in precision medicine. Currently, no PARG-targeted drugs are available commercially, with the most advanced candidates still in the Phase I clinical trial stage. Herein, we described the route screening and process development for SYN419, a potent PARG inhibitor. The critical imidazo[1,5-a]pyridine core 18 was successfully scaled up to kilogram production. Utilizing 13-step parallel reactions, we obtained the target compound SYN419 and scaled up to tens of grams, quickly fulfilling the material requirement for pre-toxicological study.
{"title":"Efficient synthesis of imidazo[1,5-a]pyridine sulfonamido derivative as a PARG inhibitor","authors":"Chao Kan , Chongxun Ge , Song Liu , Song Shi , Hu He , Weike Su","doi":"10.1016/j.tet.2025.134519","DOIUrl":"10.1016/j.tet.2025.134519","url":null,"abstract":"<div><div>The potential of PARG, the most active dePARylation enzyme, as a therapeutic target lies in its synthetic lethal relationship with other DNA repair genes. The development of PARG inhibitors represents a significant advancement in precision medicine. Currently, no PARG-targeted drugs are available commercially, with the most advanced candidates still in the Phase I clinical trial stage. Herein, we described the route screening and process development for <strong>SYN419</strong>, a potent PARG inhibitor. The critical imidazo[1,5-<em>a</em>]pyridine core <strong>18</strong> was successfully scaled up to kilogram production. Utilizing 13-step parallel reactions, we obtained the target compound <strong>SYN419</strong> and scaled up to tens of grams, quickly fulfilling the material requirement for pre-toxicological study.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"175 ","pages":"Article 134519"},"PeriodicalIF":2.1,"publicationDate":"2025-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143360207","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}
Pub Date : 2025-01-30DOI: 10.1016/j.tet.2025.134515
Dmitrii A. Aksenov , Gilberto E. Fernandez , Iliya K. Kuzminov , Nikolai A. Arutiunov , Elena V. Aleksandrova , Alexander V. Aksenov , Alexandra Vernaza , Jeadyn Ramirez , Kieran Ross , Jadyn L. Smith , Liqin Du , Puppala Sathish , Dean J. Tantillo , Alexander Kornienko
There have been a limited number of reports describing the preparation of 2-(indol-2-yl)-2-arylacetamides and those syntheses that have been published suffer from significant drawbacks. In addition, this class of compounds has not been evaluated biologically despite the occurrence of 2-(indol-2-yl)-acetamides in natural products and medicinally important compounds. We developed a two-step synthesis of these compounds utilizing our previously developed preparation of 2-(3-oxoindolin-ylidene)-2-arylacetonitriles from o-nitroacetophenones and their transformation into the desired compounds utilizing a novel process involving treatment under mild conditions with NaBH4 in EtOH. The synthesized compounds were evaluated for antiproliferative effects against BE(2)-C neuroblastoma cells and two compounds were found to have micromolar IC50 values.
{"title":"Convenient synthesis and antiproliferative activity of 2-(Indol-2-yl)-2-arylacetamides","authors":"Dmitrii A. Aksenov , Gilberto E. Fernandez , Iliya K. Kuzminov , Nikolai A. Arutiunov , Elena V. Aleksandrova , Alexander V. Aksenov , Alexandra Vernaza , Jeadyn Ramirez , Kieran Ross , Jadyn L. Smith , Liqin Du , Puppala Sathish , Dean J. Tantillo , Alexander Kornienko","doi":"10.1016/j.tet.2025.134515","DOIUrl":"10.1016/j.tet.2025.134515","url":null,"abstract":"<div><div>There have been a limited number of reports describing the preparation of 2-(indol-2-yl)-2-arylacetamides and those syntheses that have been published suffer from significant drawbacks. In addition, this class of compounds has not been evaluated biologically despite the occurrence of 2-(indol-2-yl)-acetamides in natural products and medicinally important compounds. We developed a two-step synthesis of these compounds utilizing our previously developed preparation of 2-(3-oxoindolin-ylidene)-2-arylacetonitriles from <em>o</em>-nitroacetophenones and their transformation into the desired compounds utilizing a novel process involving treatment under mild conditions with NaBH<sub>4</sub> in EtOH. The synthesized compounds were evaluated for antiproliferative effects against BE(2)-C neuroblastoma cells and two compounds were found to have micromolar IC<sub>50</sub> values.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"175 ","pages":"Article 134515"},"PeriodicalIF":2.1,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143346712","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}
Pub Date : 2025-01-28DOI: 10.1016/j.tet.2025.134506
Weiwei Yao , Zixi Xie , Xinyu Liu , Zhenpu Wang , Fei Xue , Mengtao Ma
Herein, we report the development of an efficient and straightforward electrochemical oxidation methodology for synthesizing 4-sulfonylisoquinolin-1(2H)-ones. The protocol exhibits remarkable versatility, accommodating a broad substrate scope and tolerating a wide range of functional groups, thereby enabling successful large-scale applications. Preliminary mechanistic studies suggest that the electrochemical oxidation generates an N-radical, which subsequently isomerizes to a C-radical.
{"title":"Controlled Electrochemical C4 Sulfonylation of 1(2H)-isoquinolone derivatives: Through the isomerization of N-radical to C-radical","authors":"Weiwei Yao , Zixi Xie , Xinyu Liu , Zhenpu Wang , Fei Xue , Mengtao Ma","doi":"10.1016/j.tet.2025.134506","DOIUrl":"10.1016/j.tet.2025.134506","url":null,"abstract":"<div><div>Herein, we report the development of an efficient and straightforward electrochemical oxidation methodology for synthesizing 4-sulfonylisoquinolin-1(2<em>H</em>)-ones. The protocol exhibits remarkable versatility, accommodating a broad substrate scope and tolerating a wide range of functional groups, thereby enabling successful large-scale applications. Preliminary mechanistic studies suggest that the electrochemical oxidation generates an N-radical, which subsequently isomerizes to a C-radical.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134506"},"PeriodicalIF":2.1,"publicationDate":"2025-01-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343120","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}
Pub Date : 2025-01-27DOI: 10.1016/j.tet.2025.134507
Man Zhang , Jia Rui , Chong Yu , Mengyang Sun , Dan Gou , Haifeng Wang , Guangyue Su
Six compounds were isolated from the ethyl acetate extract of the marine fungus Aspergillus japonicas, which was collected from surface seawater in the Arctic 6700-4 sea area, including two new gentisyl alcohol derivatives named dimeric terrestrol I (1) and dimeric terrestrol J (2), along with four known compounds, dimeric terrestrol E (3), 2-(hydroxymethyl) benzene-1,4-diol (4), methyl (2′,5′-dihydroxyphenyl) acetate (5), and toluhydroquinone (6). All compounds were characterized and established by spectral analysis of 1D NMR and reported data, confirmed using 2D NMR and HR-MS for new compounds. All the compounds were tested for in vitro activity. The results show that dimeric terrestrol J (2), alleviated lipopolysaccharide (LPS)-induced BV2 microglial cell death by reducing the generation of nitric oxide (NO), has strong anti-inflammatory activity and is even stronger than Dexamethasone (DEX). Furthermore, molecular docking was conducted to verify the affinity between the protein and ligand.
{"title":"New gentisyl alcohol derivatives from Aspergillus japonicas collected from the Arctic 6700-4 sea area","authors":"Man Zhang , Jia Rui , Chong Yu , Mengyang Sun , Dan Gou , Haifeng Wang , Guangyue Su","doi":"10.1016/j.tet.2025.134507","DOIUrl":"10.1016/j.tet.2025.134507","url":null,"abstract":"<div><div>Six compounds were isolated from the ethyl acetate extract of the marine fungus <em>Aspergillus japonicas</em>, which was collected from surface seawater in the Arctic 6700-4 sea area, including two new gentisyl alcohol derivatives named dimeric terrestrol I (<strong>1</strong>) and dimeric terrestrol J (<strong>2</strong>), along with four known compounds, dimeric terrestrol E (<strong>3</strong>), 2-(hydroxymethyl) benzene-1,4-diol (<strong>4</strong>), methyl (2′,5′-dihydroxyphenyl) acetate (<strong>5</strong>), and toluhydroquinone (<strong>6</strong>). All compounds were characterized and established by spectral analysis of 1D NMR and reported data, confirmed using 2D NMR and HR-MS for new compounds. All the compounds were tested for <em>in vitro</em> activity. The results show that dimeric terrestrol J (<strong>2</strong>), alleviated lipopolysaccharide (LPS)-induced BV2 microglial cell death by reducing the generation of nitric oxide (NO), has strong anti-inflammatory activity and is even stronger than Dexamethasone (DEX). Furthermore, molecular docking was conducted to verify the affinity between the protein and ligand.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134507"},"PeriodicalIF":2.1,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343116","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}
Pub Date : 2025-01-27DOI: 10.1016/j.tet.2025.134508
Shuting Yin , Fangyao Su , Jinlong Yu , Xixuan Zhao , Yongguo Liu , Sen Liang , Baoguo Sun , Hongyu Tian , Shuang Bai
2-Acetyl-1-pyrroline is the most important flavor compound of rice. However, despite its high practical value as a flavoring compound, its synthesis remains a considerable challenge. This study developed a simplified and practical approach for synthesizing 2-acetyl-1-pyrroline, using methyl prolinate as the starting material through a Grignard reaction of 2-(methoxycarbonyl)-1-pyrroline with MeMgBr in the presence of Et3N/TMSCl or TMSOTf. It was found that adding Et3N/TMSCl or TMSOTf during the Grignard reaction effectively suppresses the formation of the byproduct, the tertiary alcohol 2-(1-hydroxy-1-methylethyl)-1-pyrroline, which results from the excessive addition of the Grignard reagent. This optimized method consistently achieves stable yields of around 50 %. Furthermore, the study analyzes and discusses the formation of an isomer of 2-acetyl-1-pyrroline, specifically 6-methyl-5-oxo-2,3,4,5-tetrahydropyridine, as well as the reactivity of the 2-(methoxycarbonyl)-1-pyrroline intermediate. These findings have important implications for understanding the stability and potential applications of 2-acetyl-1-pyrroline in flavoring.
{"title":"An improved synthesis of 2-acetyl-1-pyrroline via the Grignard reaction in the presence of Et3N/TMSCl","authors":"Shuting Yin , Fangyao Su , Jinlong Yu , Xixuan Zhao , Yongguo Liu , Sen Liang , Baoguo Sun , Hongyu Tian , Shuang Bai","doi":"10.1016/j.tet.2025.134508","DOIUrl":"10.1016/j.tet.2025.134508","url":null,"abstract":"<div><div>2-Acetyl-1-pyrroline is the most important flavor compound of rice. However, despite its high practical value as a flavoring compound, its synthesis remains a considerable challenge. This study developed a simplified and practical approach for synthesizing 2-acetyl-1-pyrroline, using methyl prolinate as the starting material through a Grignard reaction of 2-(methoxycarbonyl)-1-pyrroline with MeMgBr in the presence of Et<sub>3</sub>N/TMSCl or TMSOTf. It was found that adding Et<sub>3</sub>N/TMSCl or TMSOTf during the Grignard reaction effectively suppresses the formation of the byproduct, the tertiary alcohol 2-(1-hydroxy-1-methylethyl)-1-pyrroline, which results from the excessive addition of the Grignard reagent. This optimized method consistently achieves stable yields of around 50 %. Furthermore, the study analyzes and discusses the formation of an isomer of 2-acetyl-1-pyrroline, specifically 6-methyl-5-oxo-2,3,4,5-tetrahydropyridine, as well as the reactivity of the 2-(methoxycarbonyl)-1-pyrroline intermediate. These findings have important implications for understanding the stability and potential applications of 2-acetyl-1-pyrroline in flavoring.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"175 ","pages":"Article 134508"},"PeriodicalIF":2.1,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143360825","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}
Pub Date : 2025-01-26DOI: 10.1016/j.tet.2025.134497
Yan-Ning Niu , Ke-Yu Wang , Feng-Yan Han , Xiao-Feng Xia
Nitrogen-containing dihydroisoquinolin-1(2H)-ones are widely used in various fields, such as medicine, chemical engineering, and materials. The development of novel, mild, and efficient synthetic methods has continuously aroused the interest of synthetic chemists. Recently, the radical addition tandem cyclization strategy has been considered as one of the concise and efficient methods for constructing dihydroisoquinolin-1(2H)-ones. A series of different synthetic methods for synthesizing dihydroisoquinolin-1(2H)-ones through cyclization of N-allylbenzamides with various free radical precursors are surveyed herein, including carbon-centered radicals, phosphorus-centered radicals, sulfur-centered radicals and silicon-centered radicals. The substrate scope and mechanistic details are also discussed.
{"title":"Recent developments for the synthesis of the dihydroisoquinolin-1(2H)-ones via cyclization of N-allylbenzamides","authors":"Yan-Ning Niu , Ke-Yu Wang , Feng-Yan Han , Xiao-Feng Xia","doi":"10.1016/j.tet.2025.134497","DOIUrl":"10.1016/j.tet.2025.134497","url":null,"abstract":"<div><div>Nitrogen-containing dihydroisoquinolin-1(2<em>H</em>)-ones are widely used in various fields, such as medicine, chemical engineering, and materials. The development of novel, mild, and efficient synthetic methods has continuously aroused the interest of synthetic chemists. Recently, the radical addition tandem cyclization strategy has been considered as one of the concise and efficient methods for constructing dihydroisoquinolin-1(2<em>H</em>)-ones. A series of different synthetic methods for synthesizing dihydroisoquinolin-1(2<em>H</em>)-ones through cyclization of <em>N</em>-allylbenzamides with various free radical precursors are surveyed herein, including carbon-centered radicals, phosphorus-centered radicals, sulfur-centered radicals and silicon-centered radicals. The substrate scope and mechanistic details are also discussed.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134497"},"PeriodicalIF":2.1,"publicationDate":"2025-01-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143342867","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}
The first stereoselective total synthesis of Vittarilide-B and its revised structure have been successfully accomplished. The synthesis began with D-glucal as the starting material, which was transformed into the reported structure of Vittarilide-B. Although the 1H NMR, 13C NMR, and NOE data for the synthesized compound corresponded to the naturally isolated structure, the optical rotation was inconsistent. This discrepancy necessitated the synthesis of the enantiomer using l-rhamnose as the starting material, which yielded an optical rotation consistent with that of the isolated compound. The synthesis involved the preparation of 5-deoxy-D-arabinono-1,4-lactone via RuO4-catalyzed oxidative cleavage of 6-deoxyglucal diacetate derived from D-glucal, followed by alkaline hydrolysis. The lactone was then protected with TBS, esterified with TBS-protected caffeic acid, and deprotected to afford Vittarilide-B. This synthesis not only confirmed the structure of Vittarilide-B but also resulted in the stereochemistry revision of the natural product. The revised structure was synthesized using a product whose spectral data precisely matched the reported data of Vittarilide-B, representing a noteworthy contribution to the Vittarilide family of compounds. This concise synthetic approach provides access to Vittarilide-B its stereoisomer, enabling further investigation of their biological activities.
{"title":"First stereoselective total synthesis and stereochemical revision of Vittarilide-B using a carbohydrate-based strategy","authors":"Rajashekar Reddy Nimmareddy , Rajitha Nimmareddy , Himabindu Gandham , Raju Doddipalla , Madhu Sriramadasu , Krishnakanth Reddy Leleti","doi":"10.1016/j.tet.2025.134499","DOIUrl":"10.1016/j.tet.2025.134499","url":null,"abstract":"<div><div>The first stereoselective total synthesis of Vittarilide-B and its revised structure have been successfully accomplished. The synthesis began with D-glucal as the starting material, which was transformed into the reported structure of Vittarilide-B. Although the <sup>1</sup>H NMR, <sup>13</sup>C NMR, and NOE data for the synthesized compound corresponded to the naturally isolated structure, the optical rotation was inconsistent. This discrepancy necessitated the synthesis of the enantiomer using <span>l</span>-rhamnose as the starting material, which yielded an optical rotation consistent with that of the isolated compound. The synthesis involved the preparation of 5-deoxy-D-arabinono-1,4-lactone via RuO<sub>4</sub>-catalyzed oxidative cleavage of 6-deoxyglucal diacetate derived from D-glucal, followed by alkaline hydrolysis. The lactone was then protected with TBS, esterified with TBS-protected caffeic acid, and deprotected to afford Vittarilide-B. This synthesis not only confirmed the structure of Vittarilide-B but also resulted in the stereochemistry revision of the natural product. The revised structure was synthesized using a product whose spectral data precisely matched the reported data of Vittarilide-B, representing a noteworthy contribution to the Vittarilide family of compounds. This concise synthetic approach provides access to Vittarilide-B its stereoisomer, enabling further investigation of their biological activities.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134499"},"PeriodicalIF":2.1,"publicationDate":"2025-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343121","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}
Pub Date : 2025-01-25DOI: 10.1016/j.tet.2025.134490
Celia Bustos-Brito , Pablo Yair Montaño-Hernández , Omar Salas-Huerta , Daniela Itziguari Ramírez-González , Diana Pérez-Juanchi , Juan Pablo Torres-Medicis , Martha Lydia Macías-Rubalcava , Brenda Y. Bedolla-García , Sergio Zamudio , Leovigildo Quijano , Baldomero Esquivel
Three previously undescribed diterpenoids (1–3) were isolated from the leaves of Salvia albiflora Martens & Galeotti and named salbiflorin A (1), salbiflorin B (2), and deoxysalvisousolide (3). Furthermore, six known compounds, including salvixalapadiene (4), salvihispin H (5), salvisousolide (6), tilifodiolide (7), salvigenolide (8), and 2α-hydroxy-7α-acetoxy-12-oxo-15:16-epoxy-neoclerodan-3,13(16),14-trien-18:19-olide (9) were also isolated. The structure and absolute configuration of the new compounds were established primarily through the application of 1D and 2D 1H and 13C NMR experiments, HR-DART-MS, and a combination of experimental and theoretical ECD data. Salbiflorin A (1) and B (2), constitute the first examples of a 9,10-seco-salvileucalane-derived diterpenoids. The phytotoxic activity of compounds 1−3, 6 and 8 was evaluated on the germination and root growth of four weed model species, Amaranthus hypochondriacus L., Panicum miliaceum L., Medicago sativa L., and Trifolium pratense L. Salbiflorin B (2) exhibited the highest activity in A. hypocondriacus and T. pratense, with IC50 values of 115.1 ± 3.14 and 122 ± 2.02 μM, respectively.
{"title":"Phytotoxic neo-clerodane and rearranged neo-clerodane type diterpenoids from Salvia albiflora","authors":"Celia Bustos-Brito , Pablo Yair Montaño-Hernández , Omar Salas-Huerta , Daniela Itziguari Ramírez-González , Diana Pérez-Juanchi , Juan Pablo Torres-Medicis , Martha Lydia Macías-Rubalcava , Brenda Y. Bedolla-García , Sergio Zamudio , Leovigildo Quijano , Baldomero Esquivel","doi":"10.1016/j.tet.2025.134490","DOIUrl":"10.1016/j.tet.2025.134490","url":null,"abstract":"<div><div>Three previously undescribed diterpenoids (<strong>1</strong>–<strong>3</strong>) were isolated from the leaves of <em>Salvia albiflora</em> Martens & Galeotti and named salbiflorin A (<strong>1</strong>), salbiflorin B (<strong>2</strong>), and deoxysalvisousolide (<strong>3</strong>). Furthermore, six known compounds, including salvixalapadiene (<strong>4</strong>), salvihispin H (<strong>5</strong>), salvisousolide (<strong>6</strong>), tilifodiolide (<strong>7</strong>), salvigenolide (<strong>8</strong>), and 2α-hydroxy-7α-acetoxy-12-oxo-15:16-epoxy-neoclerodan-3,13(16),14-trien-18:19-olide (<strong>9</strong>) were also isolated. The structure and absolute configuration of the new compounds were established primarily through the application of 1D and 2D <sup>1</sup>H and <sup>13</sup>C NMR experiments, HR-DART-MS, and a combination of experimental and theoretical ECD data. Salbiflorin A (<strong>1</strong>) and B (<strong>2</strong>), constitute the first examples of a 9,10-<em>seco</em>-salvileucalane-derived diterpenoids. The phytotoxic activity of compounds <strong>1</strong>−<strong>3</strong>, <strong>6</strong> and <strong>8</strong> was evaluated on the germination and root growth of four weed model species, <em>Amaranthus hypochondriacus</em> L., <em>Panicum miliaceum</em> L., <em>Medicago sativa</em> L., and <em>Trifolium pratense</em> L. Salbiflorin B (<strong>2</strong>) exhibited the highest activity in <em>A. hypocondriacus</em> and <em>T. pratense</em>, with IC<sub>50</sub> values of 115.1 ± 3.14 and 122 ± 2.02 μM, respectively.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134490"},"PeriodicalIF":2.1,"publicationDate":"2025-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343115","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Pub Date : 2025-01-25DOI: 10.1016/j.tet.2025.134498
Rebecca T. Ruck , Petr Vachal
{"title":"Prof. Eric Jacobsen and #MSDChemistry: Past, present and future","authors":"Rebecca T. Ruck , Petr Vachal","doi":"10.1016/j.tet.2025.134498","DOIUrl":"10.1016/j.tet.2025.134498","url":null,"abstract":"","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134498"},"PeriodicalIF":2.1,"publicationDate":"2025-01-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143343313","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}
Di-functionalization of alkene is a compelling area of synthetic interest due to their natural prevalence and significant antimalarial and antimicrobial activities. Nevertheless, chemoselective and regioselective peroxidation of alkenes employing various peroxy reagents is a distinct challenge and equivalent amounts of wastes are generated leading to formation of unwanted by-products and require harsh reaction conditions. On contrary, tert-butyl hydroperoxide (TBHP) associated with relatively high stability of reagent, risk minimization of overly reactive agents, and wide scope of reactions without extreme reactivity. For the first time we have highlighted the recent reports in the catalytic synthesis of acyclic peroxides using TBHP, particularly studied over the period of last 10 years. Also, we have incorporated the insight of metal catalysts and illustrated the reaction mechanism for catalytic peroxidation of various alkenes. The catalytic performance and optimization of reaction parameters are also elucidated.
{"title":"Recent advancements in catalytic peroxidation of alkenes: Synthetic approach and process optimization","authors":"Priteeparna Das, Piyusa Priyadarsan Pattanaik, Rana Chatterjee, Rambabu Dandela","doi":"10.1016/j.tet.2025.134492","DOIUrl":"10.1016/j.tet.2025.134492","url":null,"abstract":"<div><div>Di-functionalization of alkene is a compelling area of synthetic interest due to their natural prevalence and significant antimalarial and antimicrobial activities. Nevertheless, chemoselective and regioselective peroxidation of alkenes employing various peroxy reagents is a distinct challenge and equivalent amounts of wastes are generated leading to formation of unwanted by-products and require harsh reaction conditions. On contrary, <em>tert</em>-butyl hydroperoxide (TBHP) associated with relatively high stability of reagent, risk minimization of overly reactive agents, and wide scope of reactions without extreme reactivity. For the first time we have highlighted the recent reports in the catalytic synthesis of acyclic peroxides using TBHP, particularly studied over the period of last 10 years. Also, we have incorporated the insight of metal catalysts and illustrated the reaction mechanism for catalytic peroxidation of various alkenes. The catalytic performance and optimization of reaction parameters are also elucidated.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"174 ","pages":"Article 134492"},"PeriodicalIF":2.1,"publicationDate":"2025-01-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143342869","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}
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