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Electrochemical Dehydrogenative sp2-Coupling Reaction of Naphthols Accessing a Polycyclic Naphthalenone Motif
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-10 DOI: 10.1021/acs.orglett.4c03518
Julian Buchholz, Elisabeth K. Oehl, Maximilian M. Hielscher, Simone L. Kuhn, Dieter Schollmeyer, Siegfried R. Waldvogel
{"title":"Electrochemical Dehydrogenative sp2-Coupling Reaction of Naphthols Accessing a Polycyclic Naphthalenone Motif","authors":"Julian Buchholz, Elisabeth K. Oehl, Maximilian M. Hielscher, Simone L. Kuhn, Dieter Schollmeyer, Siegfried R. Waldvogel","doi":"10.1021/acs.orglett.4c03518","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03518","url":null,"abstract":"A novel polycyclic naphthalenone motif was obtained by electrochemical synthesis starting from naphthols. The process is solvent controlled, and the highly diastereoselective cyclization is due to a solvent cage. The direct, anodic dehydrogenative sp<sup>2</sup>-coupling was carried out by flow electrolysis. Ten derivatives containing this motif were synthesized in yields up to 88%, resulting in novel polycycles structurally similar to bioactive compounds like Daldionin, potentially exploring the bioactive profile.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"238 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797809","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Access to 2,3-Dihydropyridines Involving Cyano Transformation Relay through Gold Catalysis Assisted by a Lewis Acid
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-10 DOI: 10.1021/acs.orglett.4c03716
Qiuyu Meng, Ali Wang, Mingduo Lu, Yuanhong Liu
{"title":"Access to 2,3-Dihydropyridines Involving Cyano Transformation Relay through Gold Catalysis Assisted by a Lewis Acid","authors":"Qiuyu Meng, Ali Wang, Mingduo Lu, Yuanhong Liu","doi":"10.1021/acs.orglett.4c03716","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03716","url":null,"abstract":"A gold(I)-catalyzed cyclization of enynone-nitriles with amines to 2,3-DHPs assisted by La(OTf)<sub>3</sub> has been developed. The compatibility with abundant nucleophiles, high functional group tolerance, rapid assembly of molecular complexity, and late-stage functionalization of bioactive substances make this approach attractive for the construction of 2,3-DHPs, which have rarely been synthesized in the literature. The reaction proceeds via cascade cyclization involving gold/Lewis acid cooperative activation of the alkene and the cyano moiety.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"47 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797810","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Rh(II)-Catalyzed Selective C(sp3)–H/C(sp2)–H Bonds Cascade Insertion to Construct [6–8–6] Benzo-Fused Scaffold
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-10 DOI: 10.1021/acs.orglett.4c0361910.1021/acs.orglett.4c03619
Tao Yu, Feifei Fang, Haowen Shou, Yazhou Li, Zhiyan Qu, Feiyang Chen, Yu Zhang, Jiang Wang* and Hong Liu*, 
{"title":"Rh(II)-Catalyzed Selective C(sp3)–H/C(sp2)–H Bonds Cascade Insertion to Construct [6–8–6] Benzo-Fused Scaffold","authors":"Tao Yu,&nbsp;Feifei Fang,&nbsp;Haowen Shou,&nbsp;Yazhou Li,&nbsp;Zhiyan Qu,&nbsp;Feiyang Chen,&nbsp;Yu Zhang,&nbsp;Jiang Wang* and Hong Liu*,&nbsp;","doi":"10.1021/acs.orglett.4c0361910.1021/acs.orglett.4c03619","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03619https://doi.org/10.1021/acs.orglett.4c03619","url":null,"abstract":"<p >The fused eight-membered carbocycles (EMCs) play vital roles in the medicinal and biological investigations of many natural products and marketed drugs. The traditional synthesis of [6–8–6] benzo-fused derivatives involves multistep reactions and low yields, making the development of a one-step synthesis method a more challenging work. Here, we present a novel strategy for one-step construction of [6–8–6] benzo-fused scaffold from propargyl diazoacetates substituted with benzyl-nitrogen heterocyclic ring via Rh(ll)-catalyzed carbene/alkyne metathesis (CAM) and selective C–H bond insertion. This method exhibits a specific substrate scope, simple operation, mild reaction conditions, and high atom efficiency. Mechanistically, the process involves sequential CAM, 1,3-H-shift, intramolecular nucleophilic attack, and selective C(sp<sup>3</sup>)–H/C(sp<sup>2</sup>)–H bonds cascade insertion. Notably, the unique spirocyclic zwitterionic intermediate generated in this sequence contributes to <i>N</i>-heterocycle migration and fused eight-membered carbocycle formation. Additionally, the C(sp<sup>3</sup>)–H bond insertion connected to the oxygen atom rather than the nitrogen atom has been unexpectedly confirmed with the assistance of the spirocyclic zwitterionic intermediate. Overall, our findings open up a new avenue for the construction of [6–8–6] benzo-fused scaffold.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 50","pages":"10719–10728 10719–10728"},"PeriodicalIF":4.9,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.orglett.4c03619","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858622","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Late-Stage Functionalization of Guanine-Based Nucleosides, Nucleotides, and Oligonucleotide: Synthesis and Derivatization of Tricyclic Nucleoside Analogues
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-10 DOI: 10.1021/acs.orglett.4c0402410.1021/acs.orglett.4c04024
Ao-Di Ma, Wei-Jia Chen, Wen-Wu Sun* and Bin Wu*, 
{"title":"Late-Stage Functionalization of Guanine-Based Nucleosides, Nucleotides, and Oligonucleotide: Synthesis and Derivatization of Tricyclic Nucleoside Analogues","authors":"Ao-Di Ma,&nbsp;Wei-Jia Chen,&nbsp;Wen-Wu Sun* and Bin Wu*,&nbsp;","doi":"10.1021/acs.orglett.4c0402410.1021/acs.orglett.4c04024","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04024https://doi.org/10.1021/acs.orglett.4c04024","url":null,"abstract":"<p >We report here the synthesis of tricyclic nucleoside analogues via acid-catalyzed cyclization of guanine with 1,1,3,3-tetramethoxypropane. The method enables the use of hydroxyl-unprotected antiviral drugs (acyclovir, ganciclovir, and penciclovir), guanosines, oligonucleotide, and triazole-linked nucleoside dimers as substrates. Nucleoside trimer and tetramer were synthesized by derivatization reactions.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 50","pages":"10891–10896 10891–10896"},"PeriodicalIF":4.9,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858666","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Quinazolinone-to-Isoquinoline Metamorphosis by Ruthenium-Catalyzed [4+2] Annulation with Sulfoxonium Ylides
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-10 DOI: 10.1021/acs.orglett.4c0410310.1021/acs.orglett.4c04103
Xiaogang Wang*, Fei Yuan and Michal Szostak*, 
{"title":"Quinazolinone-to-Isoquinoline Metamorphosis by Ruthenium-Catalyzed [4+2] Annulation with Sulfoxonium Ylides","authors":"Xiaogang Wang*,&nbsp;Fei Yuan and Michal Szostak*,&nbsp;","doi":"10.1021/acs.orglett.4c0410310.1021/acs.orglett.4c04103","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04103https://doi.org/10.1021/acs.orglett.4c04103","url":null,"abstract":"<p >Molecular editing of quinazolinones to isoquinolines by a novel ruthenium-catalyzed [4+2] annulation with sulfoxonium ylides has been developed. The method permits the precise and rapid assembly of multisubstituted aminoisoquinolines, a class of heterocycles that play a privileged role in organic synthesis and pharmaceutical development. This new catalytic process exhibits novel programmability, including directed C–H acetylation, nucleophilic cyclization, and alcoholysis. Remarkably, various 2-arylquinazolinones and sulfoxonium ylides could be employed in excellent yields with broad functional group tolerance. This heterocycle-to-heterocycle protocol is compatible with green chemistry using an EtOH solvent and releasing H<sub>2</sub>O and dimethyl sulfoxide as byproducts.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 50","pages":"10951–10957 10951–10957"},"PeriodicalIF":4.9,"publicationDate":"2024-12-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858623","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
[Au]/[Ag]-Catalyzed Glycosidation of Ethynylcyclohexyl Glycosyl Carbonates Enables Direct Stereoselective Synthesis of 2-Azido-2-deoxy-β-mannopyranosides
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-09 DOI: 10.1021/acs.orglett.4c04208
Pratim Kumar Das, Daniil A. Ahiadorme, Niteshlal Kasdekar, Jayashree Rajput, Madhuri Vangala, David Crich, Srinivas Hotha
{"title":"[Au]/[Ag]-Catalyzed Glycosidation of Ethynylcyclohexyl Glycosyl Carbonates Enables Direct Stereoselective Synthesis of 2-Azido-2-deoxy-β-mannopyranosides","authors":"Pratim Kumar Das, Daniil A. Ahiadorme, Niteshlal Kasdekar, Jayashree Rajput, Madhuri Vangala, David Crich, Srinivas Hotha","doi":"10.1021/acs.orglett.4c04208","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04208","url":null,"abstract":"We describe the [Au]/[Ag]-catalyzed activation of ethynylcyclohexyl 2-azido-4,6-<i>O</i>-benzylidene mannosyl carbonates for β-mannosamine linkage preparation in high yield and selectivity in a temperature- and concentration-dependent manner. VT-NMR studies reveal an anomeric triflate intermediate generated in the absence of an acceptor alcohol that is stable up to −10 °C. The generality of the protocol was illustrated by successful application to a series of acceptors and by synthesis of a fully protected <i>Streptococcus pneumoniae</i> type 19F capsular trisaccharide.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"78 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142797821","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Decarboxylative Coupling of Ketoacids with Allylic Acetates
IF 5.2 1区 化学
Organic Letters Pub Date : 2024-12-09 DOI: 10.1021/acs.orglett.4c03514
Xiaoyu Zhang, Fanyi Hou, Yinlei Zhang, Bowen Li, Peizhong Xie, Teck-Peng Loh
{"title":"Decarboxylative Coupling of Ketoacids with Allylic Acetates","authors":"Xiaoyu Zhang, Fanyi Hou, Yinlei Zhang, Bowen Li, Peizhong Xie, Teck-Peng Loh","doi":"10.1021/acs.orglett.4c03514","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03514","url":null,"abstract":"We developed a novel, metal-free catalytic system for synthesizing a broad range of itaconates using α-ketoacids and allylic acetate. This method, leveraging phosphine and Mes-Acr<sup>+</sup>(BF<sub>4</sub><sup>–</sup>) catalysts, has proven versatile, enabling the efficient itaconation of peptides, the synthesis of bioactive itaconates, and the preparation of an itaconate-based bio-orthogonal probe.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"38 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142793664","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
[Au]/[Ag]-Catalyzed Glycosidation of Ethynylcyclohexyl Glycosyl Carbonates Enables Direct Stereoselective Synthesis of 2-Azido-2-deoxy-β-mannopyranosides
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-09 DOI: 10.1021/acs.orglett.4c0420810.1021/acs.orglett.4c04208
Pratim Kumar Das, Daniil A. Ahiadorme, Niteshlal Kasdekar, Jayashree Rajput, Madhuri Vangala, David Crich* and Srinivas Hotha*, 
{"title":"[Au]/[Ag]-Catalyzed Glycosidation of Ethynylcyclohexyl Glycosyl Carbonates Enables Direct Stereoselective Synthesis of 2-Azido-2-deoxy-β-mannopyranosides","authors":"Pratim Kumar Das,&nbsp;Daniil A. Ahiadorme,&nbsp;Niteshlal Kasdekar,&nbsp;Jayashree Rajput,&nbsp;Madhuri Vangala,&nbsp;David Crich* and Srinivas Hotha*,&nbsp;","doi":"10.1021/acs.orglett.4c0420810.1021/acs.orglett.4c04208","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04208https://doi.org/10.1021/acs.orglett.4c04208","url":null,"abstract":"<p >We describe the [Au]/[Ag]-catalyzed activation of ethynylcyclohexyl 2-azido-4,6-<i>O</i>-benzylidene mannosyl carbonates for β-mannosamine linkage preparation in high yield and selectivity in a temperature- and concentration-dependent manner. VT-NMR studies reveal an anomeric triflate intermediate generated in the absence of an acceptor alcohol that is stable up to −10 °C. The generality of the protocol was illustrated by successful application to a series of acceptors and by synthesis of a fully protected <i>Streptococcus pneumoniae</i> type 19F capsular trisaccharide.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 50","pages":"11034–11039 11034–11039"},"PeriodicalIF":4.9,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858684","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Halodealkenylation: Ozonolysis and Catalytic FeII with Vitamin C Convert C(sp3)–C(sp2) Bonds to C(sp3)–Halide Bonds
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-09 DOI: 10.1021/acs.orglett.4c0408410.1021/acs.orglett.4c04084
Brady W. Dehnert, Youwei Yin and Ohyun Kwon*, 
{"title":"Halodealkenylation: Ozonolysis and Catalytic FeII with Vitamin C Convert C(sp3)–C(sp2) Bonds to C(sp3)–Halide Bonds","authors":"Brady W. Dehnert,&nbsp;Youwei Yin and Ohyun Kwon*,&nbsp;","doi":"10.1021/acs.orglett.4c0408410.1021/acs.orglett.4c04084","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04084https://doi.org/10.1021/acs.orglett.4c04084","url":null,"abstract":"<p >As part of our investigations into C–C bond scission and functionalization, we report a halodealkenylation in which the C(sp<sup>3</sup>)–C(sp<sup>2</sup>) bonds of alkenes are cleaved and C(sp<sup>3</sup>)–halide bonds are formed, via a radical intermediate. These transformations occur through Criegee ozonolysis and Fe<sup>II</sup>-catalyzed reductive coupling assisted by vitamin C as a stoichiometric reductant. We applied this strategy to the formal synthesis of (<i>R,R,R</i>)-γ-tocopherol.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 50","pages":"10921–10927 10921–10927"},"PeriodicalIF":4.9,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858686","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aliphatic Alkynes and Aryl Thianthrenium Salts to Alkynones and Furanones
IF 4.9 1区 化学
Organic Letters Pub Date : 2024-12-09 DOI: 10.1021/acs.orglett.4c0351910.1021/acs.orglett.4c03519
Yan-Hua Zhao, Xing-Wei Gu and Xiao-Feng Wu*, 
{"title":"Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aliphatic Alkynes and Aryl Thianthrenium Salts to Alkynones and Furanones","authors":"Yan-Hua Zhao,&nbsp;Xing-Wei Gu and Xiao-Feng Wu*,&nbsp;","doi":"10.1021/acs.orglett.4c0351910.1021/acs.orglett.4c03519","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03519https://doi.org/10.1021/acs.orglett.4c03519","url":null,"abstract":"<p >Herein, we developed a mild and efficient palladium-catalyzed carbonylative Sonogashira coupling of aryl thianthrenium salts with aliphatic alkynes and benzyl acetylene toward alkynones and furanones. Various desired products were prepared in good yields with broad functional group tolerance including the bromide group. In the case of using benzyl acetylene, the corresponding furanones can be obtained in good yields under the same conditions with two molecules of CO inserted.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"26 50","pages":"10702–10707 10702–10707"},"PeriodicalIF":4.9,"publicationDate":"2024-12-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://pubs.acs.org/doi/epdf/10.1021/acs.orglett.4c03519","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142858693","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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