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Synthesis of Ser-Ala-Ala Cyclic Desmosine Ser-Ala-Ala环氨基葡萄糖的合成
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-07 DOI: 10.1055/a-2205-7105
Shogo Satoh, Daria Baut, Moena Hirao, Daisuke Watanabe, Rina Suzuki, Toyonori Usuki
{"title":"Synthesis of Ser-Ala-Ala Cyclic Desmosine","authors":"Shogo Satoh, Daria Baut, Moena Hirao, Daisuke Watanabe, Rina Suzuki, Toyonori Usuki","doi":"10.1055/a-2205-7105","DOIUrl":"https://doi.org/10.1055/a-2205-7105","url":null,"abstract":"Elastin is present in the extracellular matrix of various tissues, most abundantly in the aorta and major vascular vessels, and is formed by self-assembly followed by concomitant crosslinkers of tropoelastin, an elastin precursor. Desmosine is a pyridinium-based tetrafunctional amino acid that serves as an important crosslinker to bind the polymeric chains of peptides in the 3D network of elastin. Despite its significance, the detailed structure of elastin has not been elucidated. In this work, we report the synthesis of a cyclic desmosine peptide designed to mimic elastin, which could serve as a compound for mass spectrometric analysis to elucidate crosslinking structures. The synthesis involved stepwise and regioselective palladium-catalyzed cross-couplings, and inter- and intramolecular condensations.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135539780","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
Total Synthesis of the Pyrrole Alkaloids Strychnuxinal and Strychnuxin 吡咯类生物碱士的宁和士的宁的全合成
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-07 DOI: 10.1055/s-0043-1763603
Keith P. Reber, Neechi F. Okwor, Priyansh D. Gujarati
{"title":"Total Synthesis of the Pyrrole Alkaloids Strychnuxinal and Strychnuxin","authors":"Keith P. Reber, Neechi F. Okwor, Priyansh D. Gujarati","doi":"10.1055/s-0043-1763603","DOIUrl":"https://doi.org/10.1055/s-0043-1763603","url":null,"abstract":"Abstract The first asymmetric total syntheses of the fused-pyrrole alkaloids strychnuxinal and strychnuxin have been achieved in 6 and 7 steps, respectively, starting from commercially available (±)-4-chlorostyrene oxide. Key steps in the synthetic route include a regioselective epoxide opening, a reductive etherification sequence to form the central 1,4-oxazine ring, and a late-stage phenol synthesis using a mild palladium-catalyzed coupling reaction. Notably, the optimized synthetic sequence presented avoids the use of traditional protecting groups. Total synthesis of these two structurally related natural products confirmed both their constitution (via NMR and X-ray crystallography) and their absolute configuration (via optical rotation).","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135432137","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
Metal-Free Synthesis of 9-Sulfenylphenanthrenes via HNO3/HCl Promoted Annulation of 2-Alkynyl Biaryls with Disulfides HNO3/HCl促进2-炔基双芳基与二硫化物环化无金属合成9-亚砜基菲
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-06 DOI: 10.1055/a-2204-8461
Tian Luan, xiaocheng huang, Zhixiang Yao, Hui Su, Wan-Guo Yu
{"title":"Metal-Free Synthesis of 9-Sulfenylphenanthrenes via HNO3/HCl Promoted Annulation of 2-Alkynyl Biaryls with Disulfides","authors":"Tian Luan, xiaocheng huang, Zhixiang Yao, Hui Su, Wan-Guo Yu","doi":"10.1055/a-2204-8461","DOIUrl":"https://doi.org/10.1055/a-2204-8461","url":null,"abstract":"A metal-free thiolative annulation of 2-alkynylbiaryls with disulfides has been developed. This mild and efficient approach was promoted by inexpensive HNO3/HCl and afforded a range of corresponding 9-sulfenylphenanthrenes in good to excellent yields with a broad substrate scope and high functional group tolerance. Both sulfide groups of the disulfide reagent were used in the reaction.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135680017","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
Rhodium(III)-Catalyzed C–H Activation in Indole: A Comprehensive Report (2017–2022) 铑(III)在吲哚中催化C-H活化:综合报告(2017-2022)
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-06 DOI: 10.1055/s-0042-1751497
Biplab Gope, Anupam Mishra, Satish K. Awasthi
{"title":"Rhodium(III)-Catalyzed C–H Activation in Indole: A Comprehensive Report (2017–2022)","authors":"Biplab Gope, Anupam Mishra, Satish K. Awasthi","doi":"10.1055/s-0042-1751497","DOIUrl":"https://doi.org/10.1055/s-0042-1751497","url":null,"abstract":"Abstract In the realm of synthetic organic chemistry, the catalysis of directed C–H activation by transition metals is an outstanding and efficient method for the synthesis of natural products, organic materials, and fundamental organic building blocks. Notably, this strategy has experienced remarkable advances in recent years, particularly in its application to various substrate classes, including the essential indole scaffold. Indole is a highly sought-after target in organic chemistry. The significance of indole extends beyond its use in total synthesis and drug discovery. It also serves as an important tool in the development of pharmaceutical agents, agrochemicals, and materials. By targeting indole, synthetic chemists can access a wide range of bioactive compounds, which opens new avenues for drug development and chemical biology research. The synthesis of structurally varied indoles has been greatly aided by the development of a comprehensive toolkit made possible by the use of C–H activation as a versatile functionalization platform. This review highlights the latest breakthroughs in rhodium-catalyzed C–H activation at the C2, C4, and C7 positions of the indole scaffold. These developments represent significant progress in the field and hold promising potential for further advances in the synthesis of indole-based compounds. 1 Introduction 2 The Development of Rhodium-Catalyzed C–H Activation 3 General Mechanistic Introduction to Rh(III)-Catalyzed C–H Activation 4 Direct C–H Functionalization of Indoles 4.1 C2 Activation of Indoles 4.2 C4 Activation of Indoles 4.3 Dual C–H Activation Strategy 4.4 C7 Activation of Indoles 5 Conclusion","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135584916","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
Phosphine Ligand Effects in Nickel-Catalyzed Alkene Migratory Hydroalkylation 膦配体在镍催化烯烃迁移氢烷基化中的作用
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-06 DOI: 10.1055/a-2204-8921
Qing-Wei Zhu, Deguang Liu, Zhen Li, Jia-Wang Wang, Wan Nie, Xi Lu, Yao Fu
{"title":"Phosphine Ligand Effects in Nickel-Catalyzed Alkene Migratory Hydroalkylation","authors":"Qing-Wei Zhu, Deguang Liu, Zhen Li, Jia-Wang Wang, Wan Nie, Xi Lu, Yao Fu","doi":"10.1055/a-2204-8921","DOIUrl":"https://doi.org/10.1055/a-2204-8921","url":null,"abstract":"Catalytic alkene hydroalkylation has provided an efficient method for synthesizing C(sp3) centers, from readily available and inexpensive alkene starting materials through alkene hydrometallation and then cross-coupling mechanism. One of the major tasks in this field is to develop diverse ligands to achieve regioselective control. Herein, we report the investigation of nickel–triphenylphosphine catalyzed remote hydroalkylation of alkenyl amides to access α-branched amines. Various alkenes and alkyl iodides are suitable substrates to deliver desired products with excellent regioselectivities (>20:1 regioisomeric ratio). Density functional theory calculations reveal the reaction mechanism.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135680015","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 formal exchange reaction between ketones and vinyl ethers with solid catalysts 酮和乙烯醚在固体催化剂下的形式交换反应
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-03 DOI: 10.1055/a-2204-2801
Paloma Mingueza-Verdejo, Jose Pedro Cerón-Carrasco, Judit Oliver-Meseguer, Antonio Leyva-Pérez
{"title":"A formal exchange reaction between ketones and vinyl ethers with solid catalysts","authors":"Paloma Mingueza-Verdejo, Jose Pedro Cerón-Carrasco, Judit Oliver-Meseguer, Antonio Leyva-Pérez","doi":"10.1055/a-2204-2801","DOIUrl":"https://doi.org/10.1055/a-2204-2801","url":null,"abstract":"The formal exchange of functional groups in internal positions of two different molecules is of interest in synthetic chemistry, as a simple retrosynthetic strategy. Here we show the formal exchange reaction between internal α–methylene ketones and vinyl ethers, retaining the original C–O bonds. This process offers a new route for the synthesis of vinyl ethers in one step from ketones, including 1,3-diketones, under mild reaction conditions. Besides, the reaction is catalyzed by reusable cheap solids and can be carried out in flow for 20 days without signs of catalyst depletion. Combined experimental and computational mechanistic studies unveil the key role of carbonyl–enol equilibria.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135872936","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 convergent approach for the synthesis of C14-C26 fragment of anti-cancer drug eribulin mesylate 抗癌药物甲磺酸埃瑞布林C14-C26片段的聚合合成方法
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-02 DOI: 10.1055/a-2202-5597
Srihari Pabbaraja, Rajesh Nasam
{"title":"A convergent approach for the synthesis of C14-C26 fragment of anti-cancer drug eribulin mesylate","authors":"Srihari Pabbaraja, Rajesh Nasam","doi":"10.1055/a-2202-5597","DOIUrl":"https://doi.org/10.1055/a-2202-5597","url":null,"abstract":"The stereoselective synthesis of C14-C26 fragment of eribulin is reported in a convergent way by coupling of fragment C14-C19 with fragment C20-C26 that are accessible from commercially available raw materials crotonic acid and 1,4-butanediol. The key steps involved in this practical approach are Hosomi-Sakurai asymmetric alkylation, Maruoka allylation, Noyori reduction, silver catalyzed one pot rearrangement and intramolecular cyclization","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135973759","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
Recent Advances in Transition-Metal-Catalyzed Sonogashira Cross-Coupling Reactions of Alkyl Electrophiles 过渡金属催化烷基亲电试剂Sonogashira交叉偶联反应的研究进展
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-02 DOI: 10.1055/s-0042-1751506
Wei Liu, Xian Zhao
{"title":"Recent Advances in Transition-Metal-Catalyzed Sonogashira Cross-Coupling Reactions of Alkyl Electrophiles","authors":"Wei Liu, Xian Zhao","doi":"10.1055/s-0042-1751506","DOIUrl":"https://doi.org/10.1055/s-0042-1751506","url":null,"abstract":"Abstract Catalytic Sonogashira cross-coupling reactions represent an efficient and versatile approach for constructing complex alkynes from readily available starting materials. Despite notable progress in this field, the development of transition-metal-catalyzed Sonogashira cross-coupling reactions of alkyl electrophiles remains limited. This limitation primarily stems from the low reactivity and pronounced propensity of these compounds towards β-H elimination. To overcome these challenges, researchers have investigated the use of palladium, nickel, and copper catalysts for Sonogashira reactions of alkyl electrophiles. Furthermore, significant strides have been made in achieving asymmetric Sonogashira cross-coupling reactions of electrophiles. This short review provides an overview of recent breakthroughs in this area. 1 Introduction 2 Palladium-Catalyzed Sonogashira Cross-Coupling of Alkyl Halides 3 Nickel-Catalyzed Sonogashira Cross-Coupling of Alkyl Halides 4 Copper-Catalyzed Sonogashira Cross-Coupling of Alkyl Electrophiles 4.1 Copper-Catalyzed Racemic Sonogashira Cross-Coupling of Alkyl Electrophiles 4.2 Copper-catalyzed Asymmetric Sonogashira Cross-Coupling of Alkyl Electrophiles 5 Conclusions and Perspectives","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135972751","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
N-Oxide Route to the Marine Natural Product Cyanogramide D 海洋天然产物氰酰胺的n -氧化物途径
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-02 DOI: 10.1055/a-2202-7145
Dustin M. Sarnes, Valentina Struck, Peter G. Jones, Thomas Lindel
{"title":"N-Oxide Route to the Marine Natural Product Cyanogramide D","authors":"Dustin M. Sarnes, Valentina Struck, Peter G. Jones, Thomas Lindel","doi":"10.1055/a-2202-7145","DOIUrl":"https://doi.org/10.1055/a-2202-7145","url":null,"abstract":"The first synthesis of the marine natural product cyanogramide D is reported. The key step is the acetylation of a β-carboline N-oxide, followed by acetyl migration. Since in this particular case it was not possible to incorporate the styryl side chain by Buchwald coupling, a phenylethanolamine side chain was attached, which was dehydrated with Martin's sulfurane after assembly of the tetracycle. Pentacyclic products were obtained under Appel conditions. The synthesis will facilitate the exploration of the biomimetic oxidative spirocyclization of cyanogramide D to the spirooxindole cyanogramide.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135972732","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
Convenient Synthesis of Functionalized Tetracyclic Dihydrochromeno[2,3-b]pyrrolo[3,4-e]pyridine-triones via Four-Component Reactions 四组分反应合成功能化四环二氢色[2,3-b]吡咯[3,4-e]吡啶三酮
4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-02 DOI: 10.1055/s-0042-1751504
Abdolali Alizadeh, Azar Rostampoor
{"title":"Convenient Synthesis of Functionalized Tetracyclic Dihydrochromeno[2,3-b]pyrrolo[3,4-e]pyridine-triones via Four-Component Reactions","authors":"Abdolali Alizadeh, Azar Rostampoor","doi":"10.1055/s-0042-1751504","DOIUrl":"https://doi.org/10.1055/s-0042-1751504","url":null,"abstract":"Abstract In this research, a simple and efficient strategy for the straightforward synthesis of tetracyclic dihydrochromeno[2,3-b]pyrrolo[3,4-e]pyridine-trione derivatives is presented by a sequential four-component reaction of arylamines, dimethyl acetylenedicarboxylate, alkylamines, and 3-formylchromones as readily available starting materials in MeOH at room temperature. The merit of this sequential enamine formation/1,2-nucleophilic addition/intramolecular aza-Michael addition is highlighted by its high energy conserving (short reaction times at room temperature), excellent yields, metal-free catalyst, easy purification (the products can be purified by simple filtration and washing with EtOH), and green and mild conditions in a one-pot reaction. Presumably, there are no previous reports for the synthesis of these classes of heterocyclic dihydrochromeno[2,3-b]pyrrolo[3,4-e]pyridine-trione derivatives.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-11-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135973751","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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