发布求助
文献互助 智能选刊 最新文献

Organic Letters最新文献

筛选
英文 中文
Construction of 3,6-Difluoropyridones via a Double Defluorinative [3 + 3] Annulation of α-Fluoro-α-sulfonylacetamides with 2-CF3-Alkenes α-氟-α-磺酰乙酰胺与2- cf3 -烯烃双脱氟[3 + 3]环法制备3,6-二氟吡啶酮
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-08 DOI: 10.1021/acs.orglett.4c04348
Sanoop P. Chandrasekharan, Usha Yadav, Kishor Mohanan
{"title":"Construction of 3,6-Difluoropyridones via a Double Defluorinative [3 + 3] Annulation of α-Fluoro-α-sulfonylacetamides with 2-CF3-Alkenes","authors":"Sanoop P. Chandrasekharan, Usha Yadav, Kishor Mohanan","doi":"10.1021/acs.orglett.4c04348","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04348","url":null,"abstract":"A remarkably simple and efficient double defluorinative [3 + 3] annulation approach involving <i>N</i>-phenyl-α-fluoro-α-phenylsulfonylacetamide and 2-CF<sub>3</sub>-alkenes to access <i>N</i>-phenyl-3,6-difluoropyridone derivatives has been achieved. The key to the success of this single-step synthesis of difluoropyridones is the strategic utilization of 2-CF<sub>3</sub>-alkenes for consecutive allylic and vinylic substitution reactions and a desulfonylation cascade. We could also show that these difluoropyridones serve as a versatile platform for C-6-selective defluorinative functionalizations.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142935913","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
Neptunizhulides, Cryptic trans-AT Polyketide Synthase-Derived Metabolites from Paraneptunicella aestuarii NBU2194 netunizulides，隐式反式at多酮合成酶衍生的代谢物，来自aestuaripareptunicella NBU2194
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-08 DOI: 10.1021/acs.orglett.4c03801
Liwei Liu, Yanzhu Zhang, Jouni Jokela, Dacheng Wang, Matti Wahlsten, C. Benjamin Naman, Yanrong Li, Shan He
{"title":"Neptunizhulides, Cryptic trans-AT Polyketide Synthase-Derived Metabolites from Paraneptunicella aestuarii NBU2194","authors":"Liwei Liu, Yanzhu Zhang, Jouni Jokela, Dacheng Wang, Matti Wahlsten, C. Benjamin Naman, Yanrong Li, Shan He","doi":"10.1021/acs.orglett.4c03801","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03801","url":null,"abstract":"Genome mining of <i>Paraneptunicella aestuarii</i> NBU2194 resulted in the identification of a family of 17-membered macrolides, neptunizhulides A–F. Their structures were elucidated by comprehensive spectroscopic data analysis. Stereochemical assignments of the neptunizhulides were determined by <i>J</i>-based configuration analysis, ROESY NMR, Mosher’s ester derivatization, and bioinformatic predictions. Bioinformatic analysis and a <sup>15</sup>N-serine labeling experiment resulted in the identification of a putative <i>trans</i>-acyltransferase polyketide synthase (<i>trans</i>-AT PKS) biosynthetic gene cluster, and a biosynthetic pathway is proposed.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"5 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142935914","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
Intramolecular Cascade Cyclization of Cyclobutanone: Asymmetric Construction of Cyclobutanone Fused Oxa-Spirocycles 环丁酮分子内级联环化：环丁酮融合oxa -螺环的不对称结构
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-08 DOI: 10.1021/acs.orglett.4c03593
Shibaram Panda, Nikhil Dipak Chavan, Prasanta Ghorai
{"title":"Intramolecular Cascade Cyclization of Cyclobutanone: Asymmetric Construction of Cyclobutanone Fused Oxa-Spirocycles","authors":"Shibaram Panda, Nikhil Dipak Chavan, Prasanta Ghorai","doi":"10.1021/acs.orglett.4c03593","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c03593","url":null,"abstract":"The successful implementation of a cascade reaction involving a cyclobutyl unit has posed a significant challenge in achieving ring-retentive functionalization because of the ring’s sacrificial tendency. Herein, we have accomplished a cinchona-derived squaramide-catalyzed cascade reaction sequence, encompassing the desymmetrization of cyclobutanone, followed by an aldol reaction and, subsequently, a 1,4-addition step. This overall process offers a viable strategy to access architecturally fascinating oxa-spirocycles fused with cyclobutanone motifs in good yields with high optical purity.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"18 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142935912","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
Total Synthesis of Kasugamycin 卡苏加霉素的全合成
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-08 DOI: 10.1021/acs.orglett.4c04545
Ting Li, Yaling Xiang, Lingkui Meng, Qian Wan, Jing Zeng
{"title":"Total Synthesis of Kasugamycin","authors":"Ting Li, Yaling Xiang, Lingkui Meng, Qian Wan, Jing Zeng","doi":"10.1021/acs.orglett.4c04545","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04545","url":null,"abstract":"We present an efficient synthetic pathway for kasugamycin, an aminoglycoside antibiotic, utilizing naturally derived carbohydrates as starting materials. This synthesis effectively addresses stereochemical complexities by employing the selective reduction of <span>d</span>-fucal, which generates a crucial 3-deoxyglycal intermediate. This intermediate facilitates the introduction of amino groups at the C-2 and C-4 positions, which is essential for the synthesis of kasugamine. Subsequent glycosylation with glycosyl 1-<i>O</i>-<i>m</i>-chlorobenzoate (<i>m</i>CBz) donors yields a disaccharide intermediate, which is further transformed to produce kasugamycin. This streamlined approach provides a practical and effective route for the synthesis of kasugamycin and related deoxy amino sugar-containing antibiotics.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"77 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142935915","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
Photoredox-Catalyzed Alkene Acylesterification with Acyloxime Esters via C–C and Tertiary C–O Bond Formation 通过C-C和叔C-O键形成光氧化还原催化烯烃与酰基肟酯的酰基化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-07 DOI: 10.1021/acs.orglett.4c04422
Youkang Zhou, Ruiying Zhao, Mingyou Hu, Xin-Hua Duan, Le Liu
{"title":"Photoredox-Catalyzed Alkene Acylesterification with Acyloxime Esters via C–C and Tertiary C–O Bond Formation","authors":"Youkang Zhou, Ruiying Zhao, Mingyou Hu, Xin-Hua Duan, Le Liu","doi":"10.1021/acs.orglett.4c04422","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04422","url":null,"abstract":"We describe an efficient acyl esterification method for alkenes utilizing acyloxime esters as bifunctional reagents featuring radical acylation and congested C–O bond formation. This approach is characterized by mild photoredox conditions, high step and atom economy, a broad substrate scope, and excellent regioselectivity. A variety of valuable α-acyl hindered alcohol esters, including those obtained via gram-scale synthesis and late-stage functionalization of pharmaceutical molecules, were presented, demonstrating its synthetic potential and practicability.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"29 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142935916","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
Photoinduced Pd-Catalyzed 1,4-Dicarbofunctionalization of 1,3-Butadienes via Aliphatic C–H Bond Elaboration 光诱导pd催化1,3-丁二烯通过脂肪族C-H键精化的1,4-二碳功能化
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-07 DOI: 10.1021/acs.orglett.4c04410
Dan-Xing Wu, Xiao-Yun Ruan, Wen-Qian Zhang, Mostafa Sayed, Zhi-Yong Han
{"title":"Photoinduced Pd-Catalyzed 1,4-Dicarbofunctionalization of 1,3-Butadienes via Aliphatic C–H Bond Elaboration","authors":"Dan-Xing Wu, Xiao-Yun Ruan, Wen-Qian Zhang, Mostafa Sayed, Zhi-Yong Han","doi":"10.1021/acs.orglett.4c04410","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04410","url":null,"abstract":"A three-component coupling strategy for 1,4-dicarbofunctionalization of 1,3-butadiene with C–H bearing substrates has been developed using photoinduced Pd catalysis, with aryl bromide serving as the hydrogen atom transfer (HAT) reagent. This photocatalytic coupling process achieves functionalized oxindole motifs in good yield and regioselectivity under mild reaction conditions. The versatility and synthetic utility of this method are demonstrated through the addition of a variety of C–H-bearing partners and various oxindole substrates to both substituted and unsubstituted butadiene.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"29 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142935262","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
Condition-Controlled Rh(III)-Catalyzed Chemodivergent Cyclization of 2-Arylpyridines with CF3-Imidoyl Sulfoxonium Ylides via Triple C–H Activation 条件控制Rh（III）催化2-芳基吡啶与cf3 -酰基亚砜吡啶的三碳氢活化化学发散环化
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-07 DOI: 10.1021/acs.orglett.4c04514
Xiaoyang Gao, Ruirui Zhai, Juting Liao, Guiwei Yao, Hui Meng, Yuchao Luo, Dulin Kong, Shuojin Wang, Xun Chen
{"title":"Condition-Controlled Rh(III)-Catalyzed Chemodivergent Cyclization of 2-Arylpyridines with CF3-Imidoyl Sulfoxonium Ylides via Triple C–H Activation","authors":"Xiaoyang Gao, Ruirui Zhai, Juting Liao, Guiwei Yao, Hui Meng, Yuchao Luo, Dulin Kong, Shuojin Wang, Xun Chen","doi":"10.1021/acs.orglett.4c04514","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04514","url":null,"abstract":"A condition-controlled Rh(III)-catalyzed selective synthesis of CF<sub>3</sub>-substituted indoles and pyrido[2,1-<i>a</i>]isoindoles from 2-arylpyridines and CF<sub>3</sub>-imidoyl sulfoxonium ylides has been developed. The Cp*Rh(MeCN)<sub>3</sub>(SbF<sub>6</sub>)<sub>2</sub>/HFIP system afforded CF<sub>3</sub>-substituted indoles via triple C–H activation, while the [Cp*RhCl<sub>2</sub>]<sub>2</sub>/MeCN condition selectively furnished CF<sub>3</sub>-substituted pyrido[2,1-<i>a</i>]isoindoles through C–H [4 + 1] annulation. The notable advantages of this developed method included readily available starting materials, broad substrate scope, and excellent chemoselectivity. Importantly, several selected products showed promising antitumor activities.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"18 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142935265","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
Visible-Light-Triggered Mn2(CO)10-Catalyzed Carbonylation of (Hetero)aryl Chlorides 可见光触发Mn2(CO)10催化（杂）芳基氯化物羰基化
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-07 DOI: 10.1021/acs.orglett.4c04557
Yonggang Yan, Pengpeng Wang, Shasha Li, Jianyang Dong, Gang Li, Chao Wang, Dong Xue
{"title":"Visible-Light-Triggered Mn2(CO)10-Catalyzed Carbonylation of (Hetero)aryl Chlorides","authors":"Yonggang Yan, Pengpeng Wang, Shasha Li, Jianyang Dong, Gang Li, Chao Wang, Dong Xue","doi":"10.1021/acs.orglett.4c04557","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04557","url":null,"abstract":"Carbonylation of aryl electrophiles is an important method for constructing aromatic carbonyl compounds for materials science and pharmaceutical applications. However, there have been few studies on the carbonylation of abundant, inexpensive aryl chlorides. Moreover, the existing carbonylation methods usually require a high temperature, control of the CO pressure, and structurally complex catalysts and ligands. We herein report a mild, operationally simple method for visible-light-triggered amino- and alkoxycarbonylation of inert (hetero)aryl chlorides with Mn<sub>2</sub>(CO)<sub>10</sub> as both a catalyst and solid CO source at room temperature. This method, which does not require external metal catalyst, photosensitizer, or CO gas, is also suitable for other coupling partners, including aryl bromide and iodide, phenol, or arylamine derivatives.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"66 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142935266","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
Metal- and Light-Free Decarboxylative Giese Addition Reaction Facilitated by Hantzsch Ester 汉氏酯催化的无金属脱氧性脱氧性吉斯加成反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-07 DOI: 10.1021/acs.orglett.4c04496
Lei Liang, Xiao-Shan Deng, Jing Wang, Ming Jia, Xing-Yu Zhu, Yong Zhang, Shuai Yuan, Song-Lin Wang, Hai-Ming Guo, Hong-Ying Niu
{"title":"Metal- and Light-Free Decarboxylative Giese Addition Reaction Facilitated by Hantzsch Ester","authors":"Lei Liang, Xiao-Shan Deng, Jing Wang, Ming Jia, Xing-Yu Zhu, Yong Zhang, Shuai Yuan, Song-Lin Wang, Hai-Ming Guo, Hong-Ying Niu","doi":"10.1021/acs.orglett.4c04496","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04496","url":null,"abstract":"We have developed a novel strategy for decarboxylative radical addition reactions that employs ground-state reduced nicotinamide adenine dinucleotide (NADH) analogues under ambient and open-air conditions, facilitating the efficient formation of Csp<sup>3</sup>–Csp<sup>3</sup> bonds in a variety of substrates. This protocol is distinguished by its operational simplicity, mild reaction conditions, high efficiency, and the use of cost-effective starting materials. Furthermore, experimental studies have provided valuable insights into the reaction mechanism, elucidating the light-independent pathways that promote these transformations.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"62 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142935917","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
Fluorous-Phase- and Chiral-Axis-Enhanced Fluorescent Sensitivity and Chemoselectivity for Cysteine Recognition 荧光相和手性轴增强半胱氨酸识别的荧光敏感性和化学选择性
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-01-06 DOI: 10.1021/acs.orglett.4c04175
Jiaqiao Yang, Cheng Qian, Hanyu Su, Ji Zhang, Shanshan Yu, Xiaoqi Yu, Lin Pu
{"title":"Fluorous-Phase- and Chiral-Axis-Enhanced Fluorescent Sensitivity and Chemoselectivity for Cysteine Recognition","authors":"Jiaqiao Yang, Cheng Qian, Hanyu Su, Ji Zhang, Shanshan Yu, Xiaoqi Yu, Lin Pu","doi":"10.1021/acs.orglett.4c04175","DOIUrl":"https://doi.org/10.1021/acs.orglett.4c04175","url":null,"abstract":"Highly fluorinated naphthyl aldehyde <b>1</b> and binaphthyl aldehyde (<i>R</i>)-<b>2</b> were designed and synthesized for fluorous-phase-based sensing. Greatly enhanced sensitivity and chemoselectivity in going from <b>1</b> to (<i>R</i>)-<b>2</b> in the fluorescent detection of cysteine has been discovered. This is attributed to the increased structural rigidity of the axially chiral binaphthyl unit in (<i>R</i>)-<b>2</b> upon reaction with cysteine to form the corresponding thiazolidine product. The fluorous-phase-based detection of cysteine not only can allow the analysis to be conducted in a phase away from the interference of other organic and inorganic species but also results in significantly increased fluorescence response.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"37 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-01-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142929152","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
首页 上一页
0
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整，为了账户安全，请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
请完成安全验证×
相关产品
×
本文献相关产品
联系我们：info@booksci.cn Book学术提供免费学术资源搜索服务，方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号：481959085
Book学术官方微信