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Stereoselective Synthesis of C-Aryl-α-Glycosides by Reductive C(sp2)–C(sp3) Cross-Coupling Reaction 通过还原性 C(sp2)-C(sp3)交叉偶联反应立体选择性合成 C-芳基-α-糖苷
IF 2 4区 化学
Synlett Pub Date : 2024-07-19 DOI: 10.1055/a-2352-4760
Noyuri Kudo, Suzuka Chiba, Shunsuke Ono, Masataka Nagatoishi, Makoto Yoritate, Satoru Karasawa, Kazuteru Usui, Go Hirai
{"title":"Stereoselective Synthesis of C-Aryl-α-Glycosides by Reductive C(sp2)–C(sp3) Cross-Coupling Reaction","authors":"Noyuri Kudo, Suzuka Chiba, Shunsuke Ono, Masataka Nagatoishi, Makoto Yoritate, Satoru Karasawa, Kazuteru Usui, Go Hirai","doi":"10.1055/a-2352-4760","DOIUrl":"https://doi.org/10.1055/a-2352-4760","url":null,"abstract":"<p>\u0000<i>C</i>-Aryl glycosides have attracted considerable interest as biologically active natural products and as <i>O</i>-aryl glycoside mimetics in drug discovery. Here, we describe a straightforward synthesis of <i>C</i>-aryl glycosides by photoredox/Ni dual-catalyzed reductive cross-coupling between glycosyl bromides and aryl bromides. This methodology enables a highly α-stereoselective synthesis of <i>C</i>-aryl glucosides, galactosides, and mannosides.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"35 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-07-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141737462","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Development of a Purely Isolable (Dimorpholino)triazine-Based Reagent for the Epoxidation of Alkenes 开发用于烯烃环氧化的纯可分离（二吗啉基）三嗪试剂
IF 2 4区 化学
Synlett Pub Date : 2024-07-18 DOI: 10.1055/a-2356-8451
Hikaru Fujita, Toshiyuki Kato, Tatsuki Betsuyaku, Munetaka Kunishima
{"title":"Development of a Purely Isolable (Dimorpholino)triazine-Based Reagent for the Epoxidation of Alkenes","authors":"Hikaru Fujita, Toshiyuki Kato, Tatsuki Betsuyaku, Munetaka Kunishima","doi":"10.1055/a-2356-8451","DOIUrl":"https://doi.org/10.1055/a-2356-8451","url":null,"abstract":"<p>A triazine-based reagent, 2-hydroperoxy-4,6-dimorpholino-1,3,5-triazine (Triazox-II), was developed for alkene epoxidation. This reagent can be prepared from inexpensive starting materials (cyanuric chloride and morpholine) on a 15 mmol scale in two steps with 54% overall yield and isolated as a pure, bench-stable solid with low sensitivity to impact and friction. Triazox-II exhibited higher solubility in chlorinated solvents than the previously reported reagent Triazox. Epoxidation using Triazox-II was conducted in various solvents, with a preference for CH<sub>2</sub>Cl<sub>2</sub> at 0.5 M concentration, resulting in epoxides in 83–94% yield. The reaction was conducted under mild conditions owing to the low acidity of the reaction coproduct.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"26 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141737464","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
New Dephenylated Analogues of (–)-Goniofufurone: Optimization of Synthesis from l-Xylose (-)-呋喃酮的新脱苯类似物：从 l-木糖优化合成
IF 2 4区 化学
Synlett Pub Date : 2024-07-18 DOI: 10.1055/a-2352-9691
Sladjana Stanisavljević, Mirjana Popsavin, Vesna Kojić, Goran Benedeković, Velimir Popsavin, Bojana Srećo Zelenović
{"title":"New Dephenylated Analogues of (–)-Goniofufurone: Optimization of Synthesis from l-Xylose","authors":"Sladjana Stanisavljević, Mirjana Popsavin, Vesna Kojić, Goran Benedeković, Velimir Popsavin, Bojana Srećo Zelenović","doi":"10.1055/a-2352-9691","DOIUrl":"https://doi.org/10.1055/a-2352-9691","url":null,"abstract":"<p>Natural products containing highly oxygenated furanofuranone fragments are known for their potent biological activity, but also for their challenging total synthesis. In this study, the synthesis of five novel dephenylated (–)-goniofufurone analogues was completed and their cytotoxic activity against eight malignant and one normal human cell line was evaluated. Compared with previous syntheses of similar analogues, the synthesis was carried out starting from <sc>l</sc>-xylose, resulting in improved yields and a reduced number of synthetic steps for three divergent intermediates.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"8 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-07-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141737463","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
On the Existence and Relevance of Copper(III) Fluorides in Oxidative Trifluoromethylation 氧化三氟甲基化中铜（III）氟化物的存在及其相关性
IF 2 4区 化学
Synlett Pub Date : 2024-07-16 DOI: 10.1055/a-2351-5090
Daniel Joven-Sancho, Noel Nebra
{"title":"On the Existence and Relevance of Copper(III) Fluorides in Oxidative Trifluoromethylation","authors":"Daniel Joven-Sancho, Noel Nebra","doi":"10.1055/a-2351-5090","DOIUrl":"https://doi.org/10.1055/a-2351-5090","url":null,"abstract":"<p>Numerous reports invoke Cu<sup>III</sup>–F intermediates engaging in oxidative cross-couplings mediated by low/mid-valent copper and formal sources of ‘F<sup>+</sup>’ oxidants. These elusive and typically instable Cu<sup>III</sup> fluorides have been rarely characterized or spectroscopically identified, making their existence and participation within catalytic cycles somehow questionable. We have authenticated a stable organocopper(III) fluoride that undergoes C<sub>sp</sub>–CF<sub>3</sub> bond formation upon addition of silyl-capped alkynes following a 2 e<sup>–</sup> Cu<sup>III</sup>/Cu<sup>I</sup> redox shuttle. This finding strongly supports the intermediacy of Cu<sup>III</sup> fluorides in C–C coupling. We review herein the state of the art about well-defined Cu<sup>III</sup> fluorides enabling cross-coupling reactions.</p> <p>1 Introduction</p> <p>2 Brief History of Coupling-Competent Cu<sup>III</sup> Fluorides</p> <p>3 Design of an Isolable – yet Reactive – Organocopper(III) Fluoride</p> <p>4 Alkyne Trifluoromethylation: Scope and Mechanism</p> <p>5 Extension to Aryl–CF<sub>3</sub> and C–Heteroatom Couplings</p> <p>6 Summary and Outlook</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"6 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141720146","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Base-Promoted Reaction between N-Acyl Benzotriazoles and p-Toluenesulfonylmethyl Isocyanide (TosMIC): A Facile Synthesis of 4,5-Disubstituted Oxazoles 碱促进 N-酰基苯并三唑与对甲苯磺酰甲基异氰酸酯 (TosMIC) 的反应：4,5-二取代噁唑的简单合成
IF 2 4区 化学
Synlett Pub Date : 2024-07-15 DOI: 10.1055/a-2352-4950
Hui You, Daming Liu, Mengni Pan, Yue Shen, Yang Li, Wanfang Li
{"title":"Base-Promoted Reaction between N-Acyl Benzotriazoles and p-Toluenesulfonylmethyl Isocyanide (TosMIC): A Facile Synthesis of 4,5-Disubstituted Oxazoles","authors":"Hui You, Daming Liu, Mengni Pan, Yue Shen, Yang Li, Wanfang Li","doi":"10.1055/a-2352-4950","DOIUrl":"https://doi.org/10.1055/a-2352-4950","url":null,"abstract":"<p>We herein developed a base-promoted cyclization reaction between <i>N</i>-acyl benzotriazoles and <i>p</i>-toluenesulfonylmethyl isocyanide (TosMIC) to afford 4,5-disubstituted oxazoles. In the presence of 3 equiv of K<sub>3</sub>PO<sub>4</sub>, the two readily available starting materials reacted in <i>N</i>,<i>N</i>-dimethylformamide at 80 °C to give 28 examples of 4-tosyl-5-aryl, -alkyl, or -alkenyl-substituted oxazoles in moderate to high yields.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"73 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141720147","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
An Indium(III) Triflate Catalyzed Simple and Efficient One-Pot Synthesis of Substituted 3,3-Diaryloxindoles and Bis(indol-3-yl) methanes from Indoles and Isatins or Aryl Aldehydes 以吲哚和异汀类或芳基醛为原料，在三氟化硫铟（III）催化下简单高效地一步法合成取代的 3,3-二芳基吲哚和双（吲哚-3-基）甲烷
IF 2 4区 化学
Synlett Pub Date : 2024-07-15 DOI: 10.1055/a-2351-7008
Narra Laxmana Rao, Kolakaluri Chaguru Swamy, Mohan Lakshmi Punna Rao Alapati, Vemulapalli Vandana
{"title":"An Indium(III) Triflate Catalyzed Simple and Efficient One-Pot Synthesis of Substituted 3,3-Diaryloxindoles and Bis(indol-3-yl) methanes from Indoles and Isatins or Aryl Aldehydes","authors":"Narra Laxmana Rao, Kolakaluri Chaguru Swamy, Mohan Lakshmi Punna Rao Alapati, Vemulapalli Vandana","doi":"10.1055/a-2351-7008","DOIUrl":"https://doi.org/10.1055/a-2351-7008","url":null,"abstract":"<p>Indium(III) triflate was found to be an efficient metal catalyst for the electrophilic substitution reaction of substituted indoles with various isatins or aryl aldehydes in acetonitrile solvent to afford the corresponding 3,3-diaryloxindoles or bis(indol-3-yl)methanes, respectively, in high yields at room temperature. This new procedure has remarkable features such as experimental simplicity, high conversions, good to excellent yields, short reaction times, and simple workup procedures</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"29 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141720156","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
A Homolytic Substitution Approach for Directing Group-Free Nickel-Catalyzed Dialkylation of Unactivated Alkenes 引导无基团镍催化未活化烯烃二烷基化的均聚取代方法
IF 2 4区 化学
Synlett Pub Date : 2024-07-15 DOI: 10.1055/a-2352-4902
Fei Cong, Jun Wei Ng, Ming Joo Koh
{"title":"A Homolytic Substitution Approach for Directing Group-Free Nickel-Catalyzed Dialkylation of Unactivated Alkenes","authors":"Fei Cong, Jun Wei Ng, Ming Joo Koh","doi":"10.1055/a-2352-4902","DOIUrl":"https://doi.org/10.1055/a-2352-4902","url":null,"abstract":"<p>The selective construction of two C(sp<sup>3</sup>)–C(sp<sup>3</sup>) bonds through trimolecular cross-coupling of unactivated alkenes remains one of the most difficult challenges in organic synthesis. Despite previous advances in metal-catalyzed coupling for the dicarbofunctionalization of alkenes, dialkylation is still problematic due to the instability of the requisite metal–alkyl intermediate, which undergoes facile β-hydride elimination or protodemetalation. Recently, our group was successful in developing a bimolecular homolytic substitution (S<sub>H</sub>2) strategy that circumvents metal–alkyl side reactions and accomplishes the challenging cross-coupling of metal–alkyl intermediates with alkyl radicals in the absence of a directing auxiliary, permitting a highly regioselective dialkylation of unactivated alkenes.</p> <p>1\tIntroduction</p> <p>2 Nickel-Catalyzed Dicarbofunctionalization of Unactivated Alkenes</p> <p>3\tNickel-Catalyzed Dialkylation of Unactivated Alkenes</p> <p>4 Conclusions and Perspectives</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"65 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141720148","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Gram-Scale Synthesis of (±)-Tylophorine (±)-Tylophorine 的革兰氏级合成
IF 2 4区 化学
Synlett Pub Date : 2024-07-15 DOI: 10.1055/a-2351-4828
Dattatraya P. Masal, D. Srinivasa Reddy
{"title":"Gram-Scale Synthesis of (±)-Tylophorine","authors":"Dattatraya P. Masal, D. Srinivasa Reddy","doi":"10.1055/a-2351-4828","DOIUrl":"https://doi.org/10.1055/a-2351-4828","url":null,"abstract":"<p>We report a practical scalable synthesis of the natural product (±)-tylophorine by using an operationally simple protecting-group-free route from readily accessible starting materials. Synthesis of a cyclic <i>N</i>-acetyl diester compound through cyclization, followed by two key steps (decarboxylation and a Clemmensen reduction), provides access to the target molecule.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"55 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-07-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141720153","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Highly Regio-/Stereoselective Synthesis of Carbohydrates with Unsaturated Glycosyl Donors under Mild Conditions 在温和条件下与不饱和糖基供体高度区域/全选择性合成碳水化合物
IF 2 4区 化学
Synlett Pub Date : 2024-07-10 DOI: 10.1055/a-2348-2803
Xinyu Gao, Keke Ren, Lijuan Ma, Nengzhong Wang, Nianyu Huang, Hui Yao
{"title":"Highly Regio-/Stereoselective Synthesis of Carbohydrates with Unsaturated Glycosyl Donors under Mild Conditions","authors":"Xinyu Gao, Keke Ren, Lijuan Ma, Nengzhong Wang, Nianyu Huang, Hui Yao","doi":"10.1055/a-2348-2803","DOIUrl":"https://doi.org/10.1055/a-2348-2803","url":null,"abstract":"<p>Carbohydrates and their conjugates play important roles in life activities and drug development. Our group was committed to the general and effective glycosylation methods and their application in chemical biology using unsaturated glycosyl donors. In the past five years, we have reported several synthetic strategies with high stereoselectivity and milder conditions compared with previous works. In particular, high chemo-/regio- and stereoselective <i>O</i>-glycosylation, <i>C</i>-glycosylation and <i>S</i>-glycosylation could be achieved via palladium catalysis under open-air conditions at room temperature. In this Account, we will introduce our research progress in constructing four types of glycosides.</p> <p>1 Introduction</p> <p>2 Stereoselective Synthesis of <i>O</i>-Glycosides</p> <p>3 Stereoselective Synthesis of <i>C</i>-Glycosides</p> <p>4 Stereoselective Synthesis of <i>N</i>-Glycosides</p> <p>5 Stereoselective Synthesis of <i>S</i>-Glycosides</p> <p>6 Conclusion</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"22 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-07-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141587351","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
New Polymeric Disulfonimide for Heterogeneous Silicon Lewis Acid Catalysis 用于异质硅路易斯酸催化的新型聚合物二磺酰亚胺
IF 2 4区 化学
Synlett Pub Date : 2024-07-09 DOI: 10.1055/a-2349-1863
Giuliana Giorgianni, Maria Edith Casacchia, Pier Carlo Ricci, Simone Di Muzio, Andrea Lazzarini, Armando Carlone, Fabio Pesciaioli
{"title":"New Polymeric Disulfonimide for Heterogeneous Silicon Lewis Acid Catalysis","authors":"Giuliana Giorgianni, Maria Edith Casacchia, Pier Carlo Ricci, Simone Di Muzio, Andrea Lazzarini, Armando Carlone, Fabio Pesciaioli","doi":"10.1055/a-2349-1863","DOIUrl":"https://doi.org/10.1055/a-2349-1863","url":null,"abstract":"<p>A new heterogeneous polymeric disulfonimide was very easily synthesized from simple commercially available reagents. The new cost-effective catalytic material exhibited a tremendously enhanced reactivity in a benchmark Mukaiyama aldol reaction via silicon Lewis acid activation when compared with common acidic resins. Moreover, the reported polymeric disulfonimide exhibits outstanding robustness, as confirmed by its good thermal stability and excellent recyclability.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"25 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-07-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"141571846","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
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