Pub Date : 2026-02-25Epub Date: 2025-12-30DOI: 10.1002/ejoc.202501050
Lijun Shao , Yue Wang , Yibo Fu , Pan Jiang , Ruijiao Chen , Xiaochuan Chen
A new approach to antitumor renieramycin‐type alkaloids is developed based on a regio‐ and stereoselective cyclization coupling of the phenolic aldehyde and amino alcohol partners, which both were obtained from commercial N‐Cbz‐L‐tyrosine through a common synthetic process. The employment of Parikh−Doering oxidation with good functionality tolerance and successive biomimetic A‐ring modification facilitates the concise and universal approach, the utility of which is illustrated by the first synthesis of renieramycin S in 19 steps, as well as the collective syntheses of jorunnamycins A, C, jorumycin, renieramycins M, and T in 16–18 steps.
{"title":"Total Synthesis of Bis(tetrahydroisoquinoline) Alkaloids: (−)‐Renieramycin M, (−)‐Renieramycin S, (−)‐Renieramycin T, (−)‐Jorumycin, (−)‐ Jorunnamycin A, and (−)‐Jorunnamycin C","authors":"Lijun Shao , Yue Wang , Yibo Fu , Pan Jiang , Ruijiao Chen , Xiaochuan Chen","doi":"10.1002/ejoc.202501050","DOIUrl":"10.1002/ejoc.202501050","url":null,"abstract":"<div><div>A new approach to antitumor renieramycin‐type alkaloids is developed based on a regio‐ and stereoselective cyclization coupling of the phenolic aldehyde and amino alcohol partners, which both were obtained from commercial <em>N</em>‐Cbz‐L‐tyrosine through a common synthetic process. The employment of Parikh−Doering oxidation with good functionality tolerance and successive biomimetic A‐ring modification facilitates the concise and universal approach, the utility of which is illustrated by the first synthesis of renieramycin S in 19 steps, as well as the collective syntheses of jorunnamycins A, C, jorumycin, renieramycins M, and T in 16–18 steps.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 8","pages":"Article e202501050"},"PeriodicalIF":2.7,"publicationDate":"2026-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147387616","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 : 2026-02-25Epub Date: 2026-02-05DOI: 10.1002/ejoc.202500947
Martin Lepeintre , Paul Couderc , Haron Harbi , Alexia Dussart , Roy Lavendomme , Nikolay Tumanov , Johan Wouters , Benoit Colasson , Ivan Jabin
The alternate O‐methylation of p‐tBu‐calix[6]arene is a well‐known method leading to the C3v‐symmetrical 1,3,5‐tris‐O‐Me‐p‐tBu‐calix[6]arene, a key compound for the development of platforms for supramolecular studies and in particular for the access to receptors in host–guest chemistry. The alternate O‐methylation of the parent de‐tert‐butylated calix[6]arene remained elusive, precluding the development of similar C3v‐symmetrical 1,3,5‐tris‐O‐methylated receptors with an open cavity devoid of bulky tBu groups at the large rim. In this work, we developed an efficient method for the synthesis of 1,3,5‐tris‐O‐Me‐calix[6]arene. This platform was further selectively derivatized on the small and large rims, producing notably a tris‐imidazole calix[6]arene‐based ligand forming a biomimetic funnel complex upon coordinating Zn2+, with an open cavity suitable for the inclusion of a bulky dopamine derivative.
对- tbu -杯[6]芳烃的交替o -甲基化是一种众所周知的方法，导致c3v对称1,3,5-三- o -me -p- tbu -杯[6]芳烃，这是开发超分子研究平台的关键化合物，特别是在主-客体化学中获得受体的关键化合物。亲本去叔丁基杯[6]芳烃的交替o -甲基化仍然是难以捉摸的，这阻碍了类似的c3v对称1,3,5-三- o -甲基化受体的发育，这些受体具有开放的腔，在大边缘没有大的tBu基团。在本工作中，我们开发了一种合成1,3,5-三- o - me杯[6]芳烃的高效方法。该平台进一步在小环和大环上选择性衍生化，特别是产生三咪唑杯[6]芳烃基配体，在配位Zn2+后形成仿生漏斗复合物，具有适合包含大体积多巴胺衍生物的开放腔。
{"title":"Synthesis of C3v‐Symmetrical 1,3,5‐Tris‐O‐Me‐Calix[6]arene: New Perspectives","authors":"Martin Lepeintre , Paul Couderc , Haron Harbi , Alexia Dussart , Roy Lavendomme , Nikolay Tumanov , Johan Wouters , Benoit Colasson , Ivan Jabin","doi":"10.1002/ejoc.202500947","DOIUrl":"10.1002/ejoc.202500947","url":null,"abstract":"<div><div>The alternate <em>O</em>‐methylation of <em>p</em>‐<em>t</em>Bu‐calix[6]arene is a well‐known method leading to the <em>C</em><sub>3v</sub>‐symmetrical 1,3,5‐tris‐<em>O</em>‐Me‐<em>p</em>‐<em>t</em>Bu‐calix[6]arene, a key compound for the development of platforms for supramolecular studies and in particular for the access to receptors in host–guest chemistry. The alternate <em>O</em>‐methylation of the parent de‐<em>tert</em>‐butylated calix[6]arene remained elusive, precluding the development of similar <em>C</em><sub>3v</sub>‐symmetrical 1,3,5‐tris‐<em>O</em>‐methylated receptors with an open cavity devoid of bulky <em>t</em>Bu groups at the large rim. In this work, we developed an efficient method for the synthesis of 1,3,5‐tris‐<em>O</em>‐Me‐calix[6]arene. This platform was further selectively derivatized on the small and large rims, producing notably a tris‐imidazole calix[6]arene‐based ligand forming a biomimetic funnel complex upon coordinating Zn<sup>2+</sup><sub>,</sub> with an open cavity suitable for the inclusion of a bulky dopamine derivative.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 8","pages":"Article e202500947"},"PeriodicalIF":2.7,"publicationDate":"2026-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145962204","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 : 2026-02-25Epub Date: 2026-02-05DOI: 10.1002/ejoc.202501066
Karuna Thakare , Aman Singh Barahdia , Rahul Jain
We report a telescopic two‐step synthetic strategy for efficiently constructing [1H]‐1,2,3‐triazol‐4‐yl modified phenylalanine conjugates. The method combines Sonogashira coupling and a one‐pot domino reaction involving desilylation, azidation, and click chemistry. This protocol enhances the potential for peptide modification and facilitates the synthesis of polyazide derivatives that can be suitable for dendrimeric cores. This reaction yields good results and provides a scalable route, successfully accommodating a wide range of aromatic and heteroaromatic methyl bromides, while achieving excellent chiral integrity and 100% 1,4‐regioselectivity. We also explored the application of a 1,4‐disubstituted [1H]‐1,2,3‐triazol‐4‐yl phenylalanine conjugate as a directing group for C(sp2)‐H di‐halogenation.
{"title":"Telescopic Synthesis of Triazol‐4‐yl Modified Phenylalanine Conjugates and Peptide Modification Using a Sonogashira Domino Strategy at Room Temperature","authors":"Karuna Thakare , Aman Singh Barahdia , Rahul Jain","doi":"10.1002/ejoc.202501066","DOIUrl":"10.1002/ejoc.202501066","url":null,"abstract":"<div><div>We report a telescopic two‐step synthetic strategy for efficiently constructing [1<em>H</em>]‐1,2,3‐triazol‐4‐yl modified phenylalanine conjugates. The method combines Sonogashira coupling and a one‐pot domino reaction involving desilylation, azidation, and click chemistry. This protocol enhances the potential for peptide modification and facilitates the synthesis of polyazide derivatives that can be suitable for dendrimeric cores. This reaction yields good results and provides a scalable route, successfully accommodating a wide range of aromatic and heteroaromatic methyl bromides, while achieving excellent chiral integrity and 100% 1,4‐regioselectivity. We also explored the application of a 1,4‐disubstituted [1<em>H</em>]‐1,2,3‐triazol‐4‐yl phenylalanine conjugate as a directing group for C(sp<sup>2</sup>)‐H di‐halogenation.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 8","pages":"Article e202501066"},"PeriodicalIF":2.7,"publicationDate":"2026-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146070620","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}
Tetrathienoanthracene (TTA) is a π-extended derivative of anthracene fused with four thiophene rings. TTA core-based small- and macromolecules have been extensively studied in the field of organic optoelectronic materials. However, by far, the existing synthetic routes to TTA-relevant molecules all relied on the traditional multistep synthesis involving tedious substrate prefunctionalization operations (10 steps). Herein, we reported a succinct new synthetic pathway (4 steps) to TTA core-based oligoarenes via palladium-catalyzed direct CH/CBr cross-couplings. Reaction conditions for the multifold direct CH (hetero)arylations were optimized, thus allowing the smooth production of four new small molecules π-extended from the TTA core. These obtained oligoaryls were fabricated as hole-transport material in perovskite solar cells. Devices utilizing one of the TTA-based oligoaryls as hole-transport layer exhibited power conversion efficiencies up to 13.61%.
{"title":"Succinct New Synthetic Route to Tetrathienoanthracene-Based Hole-Transporting Materials via Pd-Catalyzed Direct C?H/C?Br Coupling Reactions","authors":"Ling-Hui Lu, Chu-Han Hsu, Meng-De Wu, Wei-Kai Chang, Kun-Mu Lee, Ming-Wei Hsu, Ching-Yuan Liu","doi":"10.1002/ejoc.202501195","DOIUrl":"https://doi.org/10.1002/ejoc.202501195","url":null,"abstract":"Tetrathienoanthracene (<b>TTA</b>) is a π-extended derivative of anthracene fused with four thiophene rings. <b>TTA</b> core-based small- and macromolecules have been extensively studied in the field of organic optoelectronic materials. However, by far, the existing synthetic routes to <b>TTA</b>-relevant molecules all relied on the traditional multistep synthesis involving tedious substrate prefunctionalization operations (10 steps). Herein, we reported a succinct new synthetic pathway (4 steps) to <b>TTA</b> core-based oligoarenes via palladium-catalyzed direct C<span></span>H/C<span></span>Br cross-couplings. Reaction conditions for the multifold direct C<span></span>H (hetero)arylations were optimized, thus allowing the smooth production of four new small molecules π-extended from the <b>TTA</b> core. These obtained oligoaryls were fabricated as hole-transport material in perovskite solar cells. Devices utilizing one of the <b>TTA</b>-based oligoaryls as hole-transport layer exhibited power conversion efficiencies up to 13.61%.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"57 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147320208","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 : 2026-02-25Epub Date: 2026-02-05DOI: 10.1002/ejoc.202501122
Xifu Liang , Victor Friis , Karolina Agata Szlek , Asger Munk Koue , Jesper Bendix , Lars Skjolding , Sergey Kucheryavskiy , Marco Maschietti , Christian Marcus Pedersen
Michael acceptors derived from biomass resources, such as carbohydrates, have been synthesized and their H2S scavenging properties studied. The most promising candidates were compared with the commercial H2S scavenger MEA‐triazine by studying the aqueous phase scavenging reactions using in situ Raman spectroscopy and the gas–liquid reactions were evaluated in a flow setup. Based on cost and scavenging efficiency considerations, the industrially most promising candidates were submitted to ecotoxicity studies. We have found three families of Michael acceptors, which are readily available and can be tailor‐made to serve as sulfide scavengers under different conditions.
{"title":"Biomass‐Based H2S Scavengers: Michael Acceptors","authors":"Xifu Liang , Victor Friis , Karolina Agata Szlek , Asger Munk Koue , Jesper Bendix , Lars Skjolding , Sergey Kucheryavskiy , Marco Maschietti , Christian Marcus Pedersen","doi":"10.1002/ejoc.202501122","DOIUrl":"10.1002/ejoc.202501122","url":null,"abstract":"<div><div>Michael acceptors derived from biomass resources, such as carbohydrates, have been synthesized and their H<sub>2</sub>S scavenging properties studied. The most promising candidates were compared with the commercial H<sub>2</sub>S scavenger MEA‐triazine by studying the aqueous phase scavenging reactions using in situ Raman spectroscopy and the gas–liquid reactions were evaluated in a flow setup. Based on cost and scavenging efficiency considerations, the industrially most promising candidates were submitted to ecotoxicity studies. We have found three families of Michael acceptors, which are readily available and can be tailor‐made to serve as sulfide scavengers under different conditions.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 8","pages":"Article e202501122"},"PeriodicalIF":2.7,"publicationDate":"2026-02-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146056030","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}
α-Alkylene-β-lactone is an important skeleton in a variety of biologically active molecules. It is of great significance to study the mechanism of regioselective cyclocarbonylation of tertiary alkynols catalyzed by palladium, which is applied to the synthesis of α-alkylene-β-lactone. We employed density functional theory (DFT) calculations at the M06-2X level to investigate the valence state of Pd participating in the catalytic cycle, the reaction pathways, and the mechanism of ligand-controlled regioselectivity. Our results reveal that palladium participates in the reaction with the Pd(II) oxidation state. Distortion/interaction–activation strain(D/I-AS) analyses indicate that the regioselectivity of the reaction with ligand L1 is predominantly governed by hydrogen–bond interaction in alkyne migration insertion, while the regioselectivity of the reaction with ligand L2 is mainly governed by kinetically suppressing byproduct formation.
{"title":"Regioselective Cyclocarbonylation of Alkynols: A Mechanism Study","authors":"Kaili Xie, Fengyue Zhao, Peng Dai, Qing Xia, Fang Liu, Weihua Zhang, Kendall N. Houk","doi":"10.1002/ejoc.202500698","DOIUrl":"https://doi.org/10.1002/ejoc.202500698","url":null,"abstract":"α-Alkylene-β-lactone is an important skeleton in a variety of biologically active molecules. It is of great significance to study the mechanism of regioselective cyclocarbonylation of tertiary alkynols catalyzed by palladium, which is applied to the synthesis of α-alkylene-β-lactone. We employed density functional theory (DFT) calculations at the M06-2X level to investigate the valence state of Pd participating in the catalytic cycle, the reaction pathways, and the mechanism of ligand-controlled regioselectivity. Our results reveal that palladium participates in the reaction with the Pd(II) oxidation state. Distortion/interaction–activation strain(D/I-AS) analyses indicate that the regioselectivity of the reaction with ligand <b>L1</b> is predominantly governed by hydrogen–bond interaction in alkyne migration insertion, while the regioselectivity of the reaction with ligand <b>L2</b> is mainly governed by kinetically suppressing byproduct formation.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"21 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147279583","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}
Xianyan Jiao, Maocheng Tang, Jie Luo, Deping He, Tianhao Li, Ping Liu, Jianwei Xie, Chun-Tian Li
The development of novel, efficient, and green synthetic methods for N-alkylpyrazoles represents an important objective in the realm of organic chemistry. This study presents the first 1,1′-binaphthyl-2,2′-diyl hydrogenphosphate (PA)-mediated anti-Markovnikov addition of 2-vinylindoles to diverse N-nucleophiles, including pyrazole, 2H−1,2,3-triazole, 1H-indazole, and N-methylaniline. This mild protocol affords a variety of N-alkyl pyrazole scaffolds in moderate to good yields with good regioselectivity, demonstrating broad generality toward mono-, di-, and trisubstituted alkenes. Based on deuterium-labeling and radical trapping experiments, a PA-mediated 1,4-addition ionic mechanism is proposed.
{"title":"Anti-Markovnikov Hydroamination of 2-Vinylindoles With Pyrazole Catalyzed by 1,1′-Binaphthyl-2,2′-Diyl Phosphate","authors":"Xianyan Jiao, Maocheng Tang, Jie Luo, Deping He, Tianhao Li, Ping Liu, Jianwei Xie, Chun-Tian Li","doi":"10.1002/ejoc.202501144","DOIUrl":"https://doi.org/10.1002/ejoc.202501144","url":null,"abstract":"The development of novel, efficient, and green synthetic methods for <i>N</i>-alkylpyrazoles represents an important objective in the realm of organic chemistry. This study presents the first 1,1′-binaphthyl-2,2′-diyl hydrogenphosphate (<b>PA)-</b>mediated anti-Markovnikov addition of 2-vinylindoles to diverse <i>N</i>-nucleophiles, including pyrazole, 2<i>H</i>−1,2,3-triazole, 1<i>H</i>-indazole, and <i>N</i>-methylaniline. This mild protocol affords a variety of <i>N</i>-alkyl pyrazole scaffolds in moderate to good yields with good regioselectivity, demonstrating broad generality toward mono-, di-, and trisubstituted alkenes. Based on deuterium-labeling and radical trapping experiments, a PA-mediated 1,4-addition ionic mechanism is proposed.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147287331","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}
A direct α-acylation strategy of thioesters for the synthesis of α-substituted monothiomalonates and β-thioester-Weinreb amides is described. Using carbonylimidazolides as acylating agents under LiHMDS-mediated conditions, the method provides efficient access to a broad range of previously inaccessible derivatives, including α-aryl analogs, in high yields without stoichiometric coupling reagents. The utility of the approach is demonstrated through gram-scale reactions and diverse downstream functionalizations.
{"title":"\u0000Direct α-Acylation of Thioesters With Carbonylimidazolides Toward α-Substituted Malonate Monothioates and Weinreb-Type Monoamides","authors":"Yanrong Ma, Xiaochen Wang, Xu Cao, Xinyu Wang, Hui Jin, Lixin Zhang","doi":"10.1002/ejoc.202500925","DOIUrl":"https://doi.org/10.1002/ejoc.202500925","url":null,"abstract":"A direct α-acylation strategy of thioesters for the synthesis of α-substituted monothiomalonates and β-thioester-Weinreb amides is described. Using carbonylimidazolides as acylating agents under LiHMDS-mediated conditions, the method provides efficient access to a broad range of previously inaccessible derivatives, including α-aryl analogs, in high yields without stoichiometric coupling reagents. The utility of the approach is demonstrated through gram-scale reactions and diverse downstream functionalizations<b>.</b>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"117 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"147279584","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 : 2026-02-23Epub Date: 2026-02-05DOI: 10.1002/ejoc.202501196
Faxiu Feng , Wenjun Wang , Xiaoming Liao , Zhuoran Yang , Ping Li , Xiaoxiang Zhang
A straightforward method for cleaving carbon–carbon bonds under metal‐free, base conditions was reported. Efficient synthesis of desired products with 2,3‐fused diaminoindoles scaffold is achieved by reacting 2,2‐disubstituted indolin‐3‐ones with thioureas, leveraging mild reaction conditions and a short reaction time as advantageous features of the method.
{"title":"Base‐Mediated C–C Bond Cleavage Toward 2‐(2‐oxo‐2‐Phenylethyl)‐2‐phenylindolin‐3‐ones","authors":"Faxiu Feng , Wenjun Wang , Xiaoming Liao , Zhuoran Yang , Ping Li , Xiaoxiang Zhang","doi":"10.1002/ejoc.202501196","DOIUrl":"10.1002/ejoc.202501196","url":null,"abstract":"<div><div>A straightforward method for cleaving carbon–carbon bonds under metal‐free, base conditions was reported. Efficient synthesis of desired products with 2,3‐fused diaminoindoles scaffold is achieved by reacting 2,2‐disubstituted indolin‐3‐ones with thioureas, leveraging mild reaction conditions and a short reaction time as advantageous features of the method.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"29 7","pages":"Article e202501196"},"PeriodicalIF":2.7,"publicationDate":"2026-02-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146043146","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}
Elisabeth Asmus, Martin Annau, Neanne Alnafta, David M. Barber, Guido Bojack, Birgit Bollenbach‐Wahl, Ralf Braun, Ronald W. Brown, Luke R. Churchman, Christine Dörnbrack, Andrew Earl, Tyler Fahrenhorst‐Jones, Jörg Freigang, Claudia Hartfiel, Ines Heinemann, Arnim Köhn, Bernd Laber, Michael C. McLeod, Catherine S. Meister, Gudrun Lange, Luka Posa, Shaun Rees, Dirk Schmutzler, Anna M. Reingruber, Jens Frackenpohl
The control of resistant grass weeds in cereal crops remains one of the most significant challenges in modern agriculture. Current agrochemical solutions to this problem are insufficient and rely on aging chemistry that sees ever‐increasing levels of resistance in the field, with new tools urgently needed. We present novel pyrrolidinyl carboxamide inhibitors of the plant‐specific enzyme acyl‐ACP thioesterase (FAT A) as an important advance in broadening the structural scope of agroscientific research in this area. Utilizing scaffold‐hopping and bioisosteric replacement strategies, we evolve fungicidal lead structures into promising herbicidal compounds with target affinity and in vivo efficacy on par with or slightly better than market compounds. A cocrystal structure of one of the most promising herbicide candidates with a model FAT A, alongside extensive SAR development, provides clear and comprehensive insight into the interaction of these compounds with their biological target and organisms of interest. Additionally, the structural motifs investigated here complement those of established FAT A inhibitors while employing efficient and robust syntheses, altogether building an excellent foundation for future development of similar scaffolds.
{"title":"Synthesis and Biological Profile of Substituted Pyrrolidinyl Carboxamides for Acyl‐ACP Thioesterase Inhibition","authors":"Elisabeth Asmus, Martin Annau, Neanne Alnafta, David M. Barber, Guido Bojack, Birgit Bollenbach‐Wahl, Ralf Braun, Ronald W. Brown, Luke R. Churchman, Christine Dörnbrack, Andrew Earl, Tyler Fahrenhorst‐Jones, Jörg Freigang, Claudia Hartfiel, Ines Heinemann, Arnim Köhn, Bernd Laber, Michael C. McLeod, Catherine S. Meister, Gudrun Lange, Luka Posa, Shaun Rees, Dirk Schmutzler, Anna M. Reingruber, Jens Frackenpohl","doi":"10.1002/ejoc.202500978","DOIUrl":"https://doi.org/10.1002/ejoc.202500978","url":null,"abstract":"The control of resistant grass weeds in cereal crops remains one of the most significant challenges in modern agriculture. Current agrochemical solutions to this problem are insufficient and rely on aging chemistry that sees ever‐increasing levels of resistance in the field, with new tools urgently needed. We present novel pyrrolidinyl carboxamide inhibitors of the plant‐specific enzyme acyl‐ACP thioesterase (FAT A) as an important advance in broadening the structural scope of agroscientific research in this area. Utilizing scaffold‐hopping and bioisosteric replacement strategies, we evolve fungicidal lead structures into promising herbicidal compounds with target affinity and in vivo efficacy on par with or slightly better than market compounds. A cocrystal structure of one of the most promising herbicide candidates with a model FAT A, alongside extensive SAR development, provides clear and comprehensive insight into the interaction of these compounds with their biological target and organisms of interest. Additionally, the structural motifs investigated here complement those of established FAT A inhibitors while employing efficient and robust syntheses, altogether building an excellent foundation for future development of similar scaffolds.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"336 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-02-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146778766","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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