Axially chiral biaryl aldehydes are precursors for the synthesis of axially chiral compounds and novel chiral catalysts of great interest, which play vital roles in extensive research fields. However, limited strategies exist for the efficient synthesis of axially chiral aldehydes, and the construction of structurally diverse axially chiral aldehydes remains challenging. Herein, a strategy is reported for the synthesis of biaryl axially chiral aldehydes with varying structures from biaryl dialdehydes and aromatic amines in the presence of a chiral phosphoric acid catalyst. This protocol features excellent enantioselectivity, mild conditions, and good functional-group tolerance.
{"title":"Synthesis of Chiral Axially Diaryl Aldehydes by Chiral Phosphoric Acid Catalyzed Desymmetrization Reaction","authors":"Lutong Yuan, Lixin Cui, Yuheng Liu, Wenkai Bao, Qiaohong Zhu, Xiaofei Zeng","doi":"10.1002/ejoc.202401038","DOIUrl":"https://doi.org/10.1002/ejoc.202401038","url":null,"abstract":"Axially chiral biaryl aldehydes are precursors for the synthesis of axially chiral compounds and novel chiral catalysts of great interest, which play vital roles in extensive research fields. However, limited strategies exist for the efficient synthesis of axially chiral aldehydes, and the construction of structurally diverse axially chiral aldehydes remains challenging. Herein, a strategy is reported for the synthesis of biaryl axially chiral aldehydes with varying structures from biaryl dialdehydes and aromatic amines in the presence of a chiral phosphoric acid catalyst. This protocol features excellent enantioselectivity, mild conditions, and good functional-group tolerance.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"212 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142536882","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}
Priyank Kumar Sharma, Akanksha Babbar, Sakshi Sahewal, Soumyajit Das
Cyclopenta-annulated polycyclic aromatic hydrocarbons (CP-PAHs) are of significant interest due to their unique optoelectronic properties and applications in organic electronic devices. Phenanthroacephenanthrylene (PAP) isomers are CP-PAHs that have been rarely investigated, and only the [9,10-e]PAP isomer was explored to date. Herein, we report the syntheses, crystal structure and optoelectronic properties of two PAP isomers, 7-ethoxy[2,1-e]PAP 1 and 9-ethoxy[1,2-e]PAP 2. The structural isomers were synthesized in multi-steps, and structural elucidations were performed using NMR, mass, and single-crystal X-ray diffraction analyses, revealing planar backbone of the isomers. UV-visible absorption and fluorescence spectra of compound 1 were red-shifted than that of 2, suggesting smaller HOMO–LUMO energy gap which is further validated by DFT calculations that suggested the lowering of HOMO–LUMO spacing could be attributed to the greater destabilization of HOMO for 1.
环戊烷化多环芳烃（CP-PAHs）因其独特的光电特性和在有机电子设备中的应用而备受关注。菲并蒽(PAP)异构体是很少被研究的 CP-PAHs，迄今为止只有[9,10-e]PAP 异构体被研究过。在此，我们报告了两种 PAP 异构体--7-乙氧基[2,1-e]PAP 1 和 9-乙氧基[1,2-e]PAP 2 的合成、晶体结构和光电特性。这些结构异构体是通过多个步骤合成的，并利用核磁共振、质量和单晶 X 射线衍射分析进行了结构阐释，揭示了异构体的平面骨架。化合物 1 的紫外可见吸收光谱和荧光光谱都比 2 的红移，表明其 HOMO-LUMO 能隙更小，DFT 计算进一步验证了这一点，即 HOMO-LUMO 间距的降低可能是由于 1 的 HOMO 更加不稳定。
{"title":"Syntheses and Properties of Two Isomeric Phenanthroacephenanthrylene Derivatives","authors":"Priyank Kumar Sharma, Akanksha Babbar, Sakshi Sahewal, Soumyajit Das","doi":"10.1002/ejoc.202400991","DOIUrl":"https://doi.org/10.1002/ejoc.202400991","url":null,"abstract":"Cyclopenta-annulated polycyclic aromatic hydrocarbons (CP-PAHs) are of significant interest due to their unique optoelectronic properties and applications in organic electronic devices. Phenanthroacephenanthrylene (PAP) isomers are CP-PAHs that have been rarely investigated, and only the [9,10-e]PAP isomer was explored to date. Herein, we report the syntheses, crystal structure and optoelectronic properties of two PAP isomers, 7-ethoxy[2,1-e]PAP 1 and 9-ethoxy[1,2-e]PAP 2. The structural isomers were synthesized in multi-steps, and structural elucidations were performed using NMR, mass, and single-crystal X-ray diffraction analyses, revealing planar backbone of the isomers. UV-visible absorption and fluorescence spectra of compound 1 were red-shifted than that of 2, suggesting smaller HOMO–LUMO energy gap which is further validated by DFT calculations that suggested the lowering of HOMO–LUMO spacing could be attributed to the greater destabilization of HOMO for 1.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"16 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142541920","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}
Optically active aziridines represent a pivotal class of rigid three-membered nitrogen-heterocyclic compounds found in natural products, pharmaceuticals, agrochemicals, and functional motifs, which have demonstrated outstanding practicability as therapeutic molecular frameworks, versatile synthetic endpoints, and functional materials in both academic and industrial communities. Recent years have witnessed a broad spectrum of prominent breakthroughs in the field of chiral aziridines due to the aziridine-based rigid and three-dimensional pharmacophores, which have resulted in streamlining the drug discovery process. Over the past few decades, particular attention has been directed towards the strategically efficient, versatile, and practical assembly of optically active aziridines. These synthesis approaches have demonstrated great potential in the context of the construction of pharmaceutical molecules, biologically and pharmacologically relevant natural products, and functional materials. In this review, several synthetic strategies for the assembly of chiral aziridines are summarized, which could be divided into five categories; (1) Introduction; (2) Construction of optically active aziridines via reactions of olefines with nitrene sources; (3) Construction of optically active aziridines via reactions of imines with carbenes; (4) Construction of optically active aziridines via reaction of azirines; (5) Construction of optically active aziridines via intramolecular cyclization of amine derivatives.
{"title":"Synthetic Approaches for the Construction of Chiral Aziridines","authors":"Qing-Hui Liu, Jia-Xuan Liu, Ya-Ping Han, Yong-Min Liang, Li-Zeng Peng","doi":"10.1002/ejoc.202401048","DOIUrl":"https://doi.org/10.1002/ejoc.202401048","url":null,"abstract":"Optically active aziridines represent a pivotal class of rigid three-membered nitrogen-heterocyclic compounds found in natural products, pharmaceuticals, agrochemicals, and functional motifs, which have demonstrated outstanding practicability as therapeutic molecular frameworks, versatile synthetic endpoints, and functional materials in both academic and industrial communities. Recent years have witnessed a broad spectrum of prominent breakthroughs in the field of chiral aziridines due to the aziridine-based rigid and three-dimensional pharmacophores, which have resulted in streamlining the drug discovery process. Over the past few decades, particular attention has been directed towards the strategically efficient, versatile, and practical assembly of optically active aziridines. These synthesis approaches have demonstrated great potential in the context of the construction of pharmaceutical molecules, biologically and pharmacologically relevant natural products, and functional materials. In this review, several synthetic strategies for the assembly of chiral aziridines are summarized, which could be divided into five categories; (1) Introduction; (2) Construction of optically active aziridines via reactions of olefines with nitrene sources; (3) Construction of optically active aziridines via reactions of imines with carbenes; (4) Construction of optically active aziridines via reaction of azirines; (5) Construction of optically active aziridines via intramolecular cyclization of amine derivatives.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"15 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142541913","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}
Mathilde A. C. H. Janssen, Rico Rappard, Tom Dekker, Mitchel Heiming, Marjolijn Beens, Dyon Pieters, Brian H. M. Kuijpers, Jorg C. J. Benningshof, Maikel Wijtmans, Iwan J. P. de Esch, Daniel Blanco-Ania, Floris P. J. T. Rutjes
Cyclobutanes have attracted significant interest in medicinal chemistry because of their unique structure and potential advantages in pharmacological properties. In this study a two-diversification-point library of cyclobutanesulfonamides with either carbamates or triazoles was synthesized through a hyperbaric [2+2] cycloaddition reaction between ethenesulfonyl fluoride and tert-butyl vinyl ether as the key step.
{"title":"High-Pressure-Mediated Fragment Library Synthesis of 1,2-Disubsituted Cyclobutane Derivatives","authors":"Mathilde A. C. H. Janssen, Rico Rappard, Tom Dekker, Mitchel Heiming, Marjolijn Beens, Dyon Pieters, Brian H. M. Kuijpers, Jorg C. J. Benningshof, Maikel Wijtmans, Iwan J. P. de Esch, Daniel Blanco-Ania, Floris P. J. T. Rutjes","doi":"10.1002/ejoc.202400797","DOIUrl":"https://doi.org/10.1002/ejoc.202400797","url":null,"abstract":"Cyclobutanes have attracted significant interest in medicinal chemistry because of their unique structure and potential advantages in pharmacological properties. In this study a two-diversification-point library of cyclobutanesulfonamides with either carbamates or triazoles was synthesized through a hyperbaric [2+2] cycloaddition reaction between ethenesulfonyl fluoride and <i>tert</i>-butyl vinyl ether as the key step.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"31 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142536339","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}
Martin Pošta, Margarita Dmitrieva, Chiara Volpe, Václav Matoušek, Blanka Klepetářová, Petr Beier
Copper(I)-mediated azide-alkyne cycloaddition was coupled with cross-coupling for the synthesis of [6,5,5] ring-fused tricyclic triazoles. Copper(I)-mediated azide-alkyne cycloaddition was investigated on 2-iodoaryl propynes or propynones. With catalytic amount of Cu(I) salts or with N-donor ligands on copper only the products of azide-alkyne cycloadditions were formed. However, with an equimolar amount of copper(I) iodide and triethylamine new [6,5,5] ring-fused tricyclic triazoles were formed by azide-alkyne cycloadditon coupled to a cross-coupling reaction.
{"title":"Synthesis of [6,5,5]Ring-Fused Tricyclic Triazoles by Copper-Promoted Double Cyclization","authors":"Martin Pošta, Margarita Dmitrieva, Chiara Volpe, Václav Matoušek, Blanka Klepetářová, Petr Beier","doi":"10.1002/ejoc.202400736","DOIUrl":"https://doi.org/10.1002/ejoc.202400736","url":null,"abstract":"Copper(I)-mediated azide-alkyne cycloaddition was coupled with cross-coupling for the synthesis of [6,5,5] ring-fused tricyclic triazoles. Copper(I)-mediated azide-alkyne cycloaddition was investigated on 2-iodoaryl propynes or propynones. With catalytic amount of Cu(I) salts or with N-donor ligands on copper only the products of azide-alkyne cycloadditions were formed. However, with an equimolar amount of copper(I) iodide and triethylamine new [6,5,5] ring-fused tricyclic triazoles were formed by azide-alkyne cycloadditon coupled to a cross-coupling reaction.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"15 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142490804","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}
Andrea M. Escalante, Micaela B. Riera, Mario O. Salazar, Ricardo L.E. Furlan
Traditional methods for discovering bioactive compounds can be time-consuming and resource-intensive, often requiring extensive synthesis and evaluation. To address these challenges, this study combines TLC-based assays with dithioacetal mixture-library preparation, enabling rapid and effective bioactivity screening. Tyrosinase, an enzyme crucial for melanin production and fruit browning, serves as a significant therapeutic target in this context. Despite the substantial potential of sulfur-containing compounds in medicinal chemistry, the use of dithioacetals in drug discovery remains limited. In this study, two small libraries of dithioacetals, comprising more than 150 compounds, were prepared as mixture-libraries and screened on TLC by directly measuring tyrosinase activity on the plate surface. This approach facilitated the efficient preparation and identification of a potent, simple, and readily accessible dithioacetal inhibitor of tyrosinase, with the entire process being conducted on a low milligram scale.
{"title":"Effect-Directed Synthesis of a Dithioacetal Tyrosinase Inhibitor","authors":"Andrea M. Escalante, Micaela B. Riera, Mario O. Salazar, Ricardo L.E. Furlan","doi":"10.1002/ejoc.202401006","DOIUrl":"https://doi.org/10.1002/ejoc.202401006","url":null,"abstract":"Traditional methods for discovering bioactive compounds can be time-consuming and resource-intensive, often requiring extensive synthesis and evaluation. To address these challenges, this study combines TLC-based assays with dithioacetal mixture-library preparation, enabling rapid and effective bioactivity screening. Tyrosinase, an enzyme crucial for melanin production and fruit browning, serves as a significant therapeutic target in this context. Despite the substantial potential of sulfur-containing compounds in medicinal chemistry, the use of dithioacetals in drug discovery remains limited. In this study, two small libraries of dithioacetals, comprising more than 150 compounds, were prepared as mixture-libraries and screened on TLC by directly measuring tyrosinase activity on the plate surface. This approach facilitated the efficient preparation and identification of a potent, simple, and readily accessible dithioacetal inhibitor of tyrosinase, with the entire process being conducted on a low milligram scale.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"25 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142488770","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}
M. Sc. Madeleine Giraud, M. Sc. Mathis Robin Mitha, M. Sc. Sven Klehenz, Prof. Dr. Hans-Achim Wagenknecht
The Front Cover features an abstract representation of two novel, highly reducing organophotocatalysts derived from N-arylphenothiazines and N,N-diarylphenazines, compounds widely recognized as versatile and effective photoredox catalysts. The catalysts shown are the most efficient from a library of 17 catalysts synthesized. They show remarkable performance in the addition of methanol to α-methylstyrene, which was used as a model reaction, significantly reducing the reaction time and the catalyst loading by more than 20 times. Alongside the featured catalysts, the cover shows abstract representations of photophysical and photocatalytic concepts. The authors used spectroelectrochemistry and DFT calculations to further elucidate their findings and derive structure–activity relationships that might help to further improve organophotocatalysts. More information can be found in the Research Article by H.-A. Wagenknecht and co-workers (DOI: 10.1002/ejoc.202400847).
{"title":"Front Cover: N-Arylphenothiazines and N,N-Diarylphenazines as Tailored Organophotoredox Catalysts for the Reductive Activation of Alkenes (Eur. J. Org. Chem. 40/2024)","authors":"M. Sc. Madeleine Giraud, M. Sc. Mathis Robin Mitha, M. Sc. Sven Klehenz, Prof. Dr. Hans-Achim Wagenknecht","doi":"10.1002/ejoc.202484001","DOIUrl":"10.1002/ejoc.202484001","url":null,"abstract":"<p><b>The Front Cover</b> features an abstract representation of two novel, highly reducing organophotocatalysts derived from <i>N</i>-arylphenothiazines and <i>N</i>,<i>N</i>-diarylphenazines, compounds widely recognized as versatile and effective photoredox catalysts. The catalysts shown are the most efficient from a library of 17 catalysts synthesized. They show remarkable performance in the addition of methanol to α-methylstyrene, which was used as a model reaction, significantly reducing the reaction time and the catalyst loading by more than 20 times. Alongside the featured catalysts, the cover shows abstract representations of photophysical and photocatalytic concepts. The authors used spectroelectrochemistry and DFT calculations to further elucidate their findings and derive structure–activity relationships that might help to further improve organophotocatalysts. More information can be found in the Research Article by H.-A. Wagenknecht and co-workers (DOI: 10.1002/ejoc.202400847).\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"27 40","pages":""},"PeriodicalIF":2.5,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202484001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142489826","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}
Montserrat Zidan, Lucas F. Villela, Louis Barriault
Organic transformations initiated by photochemical activation have been at the forefront of reaction discovery. In this study, we present a formal photochemical [3 + 2] and [4 + 2] cycloaddition using N-aryl cyclopropylamines and N-aryl cyclobutylamines in conjunction with α,β-unsaturated carbonyl systems, unveiling two distinct mechanistic pathways. The [3 + 2] cycloaddition is elucidated as being guided by the photochemical activity of an electron donor-acceptor (EDA) complex. Simultaneously, intermolecular [4 + 2] annulation of cyclobutylanilines is achieved by visible-light photoredox catalysis. These simple methodologies have wide applicability, facilitating the synthesis of N-arylaminocycloalkyl compounds in yields ranging from good to excellent
{"title":"Photoactivated Formal [3 + 2] / [4+2] Cycloaddition of N-Aryl Cyclopropyl and Cyclobutylamines","authors":"Montserrat Zidan, Lucas F. Villela, Louis Barriault","doi":"10.1002/ejoc.202400558","DOIUrl":"https://doi.org/10.1002/ejoc.202400558","url":null,"abstract":"Organic transformations initiated by photochemical activation have been at the forefront of reaction discovery. In this study, we present a formal photochemical [3 + 2] and [4 + 2] cycloaddition using N-aryl cyclopropylamines and N-aryl cyclobutylamines in conjunction with α,β-unsaturated carbonyl systems, unveiling two distinct mechanistic pathways. The [3 + 2] cycloaddition is elucidated as being guided by the photochemical activity of an electron donor-acceptor (EDA) complex. Simultaneously, intermolecular [4 + 2] annulation of cyclobutylanilines is achieved by visible-light photoredox catalysis. These simple methodologies have wide applicability, facilitating the synthesis of N-arylaminocycloalkyl compounds in yields ranging from good to excellent","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"34 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142488769","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}
Herein, a highly efficient five-step reaction sequence to meso-alkyl BODIPYs is presented. In our previous work, the hydroformylation of terminal alkenes was used to generate an aldehyde from an alkene via rhodium catalysis to be employed in a subsequent tandem reaction to obtain BODIPY dyes. However, the use of higher pressures and therefore autoclaves as well as their necessary equipment might limit others to use this method. The refined approach in this work employs ambient pressure hydroformylation, done in a simple Schlenk tube and using a CO/H2 balloon, as key step towards an easier meso-alkyl BODIPY synthesis. Additionally, the use of MTBE instead of chloroform as reaction solvent results in a greener approach. Readily available and easily synthesizable alkenes as well as different pyrrole building blocks can be used to extend the range of known alkyl-BODIPYs. The synthesis of 23 derivatives with overall yields of up to 67% demonstrates the wide applicability and advantages of the refined method.
{"title":"Ambient Pressure Hydroformylation – A Key Step to meso-alkyl BODIPYs","authors":"Bernhard Breit, Lukas Miller, Felix Bauer","doi":"10.1002/ejoc.202401089","DOIUrl":"https://doi.org/10.1002/ejoc.202401089","url":null,"abstract":"Herein, a highly efficient five-step reaction sequence to meso-alkyl BODIPYs is presented. In our previous work, the hydroformylation of terminal alkenes was used to generate an aldehyde from an alkene via rhodium catalysis to be employed in a subsequent tandem reaction to obtain BODIPY dyes. However, the use of higher pressures and therefore autoclaves as well as their necessary equipment might limit others to use this method. The refined approach in this work employs ambient pressure hydroformylation, done in a simple Schlenk tube and using a CO/H2 balloon, as key step towards an easier meso-alkyl BODIPY synthesis. Additionally, the use of MTBE instead of chloroform as reaction solvent results in a greener approach. Readily available and easily synthesizable alkenes as well as different pyrrole building blocks can be used to extend the range of known alkyl-BODIPYs. The synthesis of 23 derivatives with overall yields of up to 67% demonstrates the wide applicability and advantages of the refined method.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"8 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142487867","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}
Roderick W. Bates, Mikhail Elyashberg, Andrei G. Kutateladze, Craig M. Williams
Using computational methods and comparison of reported NMR data, the reported structure of setosol, an unprecedented benzoxonin fungal natural product, is shown to be incorrect. Setosol is shown to be identical to a known but unnamed diaryl ether.
{"title":"Reassignment of the Structure of Setosol","authors":"Roderick W. Bates, Mikhail Elyashberg, Andrei G. Kutateladze, Craig M. Williams","doi":"10.1002/ejoc.202400431","DOIUrl":"https://doi.org/10.1002/ejoc.202400431","url":null,"abstract":"Using computational methods and comparison of reported NMR data, the reported structure of setosol, an unprecedented benzoxonin fungal natural product, is shown to be incorrect. Setosol is shown to be identical to a known but unnamed diaryl ether.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"12 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142488771","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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