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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":"17 11","pages":"0"},"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":"2 1","pages":"0"},"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":"9 2","pages":"0"},"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":"1 2","pages":"0"},"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
Palladium-Catalyzed Dearomatization of Benzothiophenes: Isolation and Functionalization of a Discrete Dearomatized Intermediate. 钯催化苯并噻吩的脱芳：分离和官能化一种离散的脱芳中间体。
IF 2.2 4区 化学
Synthesis-Stuttgart Pub Date : 2023-11-01 Epub Date: 2023-06-13 DOI: 10.1055/a-2092-9012
Andrew John Intelli, Mohan Pal, Manikandan Selvaraju, Ryan A Altman
{"title":"Palladium-Catalyzed Dearomatization of Benzothiophenes: Isolation and Functionalization of a Discrete Dearomatized Intermediate.","authors":"Andrew John Intelli, Mohan Pal, Manikandan Selvaraju, Ryan A Altman","doi":"10.1055/a-2092-9012","DOIUrl":"10.1055/a-2092-9012","url":null,"abstract":"<p><p>A Pd-catalyzed decarboxylative dearomatization reaction of a heterocyclic substrate enables access to an uncommon reaction intermediate that rearomatizes in the presence of amine bases in a net C-H functionalization sequence. The dearomatized benzo[<i>b</i>]thiophene intermediate bears an exocyclic alkene that can be functionalized through cycloaddition and halogenation reactions to deliver complex heterocyclic products.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"55 21","pages":"3568-3574"},"PeriodicalIF":2.2,"publicationDate":"2023-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10617892/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"71428306","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Visible-Light-Enabled Radical Alkynylborylation of Activated Alkenes 活化烯烃的可见光活化自由基炔基硼化反应
4区 化学
Synthesis-Stuttgart Pub Date : 2023-10-31 DOI: 10.1055/s-0042-1751512
Jin Xie, Congjun Zhu, Shunruo Yao
{"title":"Visible-Light-Enabled Radical Alkynylborylation of Activated Alkenes","authors":"Jin Xie, Congjun Zhu, Shunruo Yao","doi":"10.1055/s-0042-1751512","DOIUrl":"https://doi.org/10.1055/s-0042-1751512","url":null,"abstract":"Abstract A photoredox-catalyzed protocol for performing radical difunctionalization of alkenes using N-heterocyclic carbene (NHC) boranes and alkynyl bromines is described. The alkynylborylation difunctionalization reaction involves photoredox generation of boryl radical, with subsequent radical addition to the double bond followed by the capture of alkynyl bromide to form a C–C bond. This method features mild reaction conditions, remarkable chemoselectivity, broad substrate scope and good to excellent yields (up to 89%). The modification of coumarin derivatives indicates that this approach can provide a useful route for the synthesis of complex alkynylborylated products.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"25 31","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135808791","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
Synthesis of Piperazin-2-one Derivatives via Cascade Double Nucleophilic Substitution 级联双亲核取代法合成哌嗪-2-酮衍生物
4区 化学
Synthesis-Stuttgart Pub Date : 2023-10-31 DOI: 10.1055/a-2201-9951
Milos Petkovic, Dusica Kusljevic, Milos Jovanovic, Predrag Jovanovic, Gordana Tasic, Milena Simic, Vladimir Savic
{"title":"Synthesis of Piperazin-2-one Derivatives via Cascade Double Nucleophilic Substitution","authors":"Milos Petkovic, Dusica Kusljevic, Milos Jovanovic, Predrag Jovanovic, Gordana Tasic, Milena Simic, Vladimir Savic","doi":"10.1055/a-2201-9951","DOIUrl":"https://doi.org/10.1055/a-2201-9951","url":null,"abstract":"A cascade, metal promoted transformations utilizing chloro allenylamide, primary amine and aryl iodide afforded piperizinones in good yields. Under the optimized conditions the cascade is performed as one-pot process allowing formation of three bonds. The synthetic route, controlled by the reaction rates of several processes involved, introduces two points of diversity and is well suited for combinatorial synthesis or related technologies.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"63 2 1","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135809109","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
Carboxamide-accelerated Chemoselective Borylation of Iodoarenes under Photoirradiation 光照射下羧胺加速碘芳烃的化学选择性硼化反应
4区 化学
Synthesis-Stuttgart Pub Date : 2023-10-31 DOI: 10.1055/a-2202-2263
Yusei Nakashima, Michinori Sumimoto, Takashi Nishikata
{"title":"Carboxamide-accelerated Chemoselective Borylation of Iodoarenes under Photoirradiation","authors":"Yusei Nakashima, Michinori Sumimoto, Takashi Nishikata","doi":"10.1055/a-2202-2263","DOIUrl":"https://doi.org/10.1055/a-2202-2263","url":null,"abstract":"Borylation of haloarene is one of the most important methodologies to synthesize borylated arenes. Generally, borylation of haloarene occurs smoothly at sterically less-hindered para- or meta-position by using a transition metal, a photoredox catalyst, or basic conditions. This study reports on ortho-specific and chemoselective borylation of ortho-iodoarene possessing carboxamide under visible-light irradiation. When a haloarene containing both C–I and C–X bonds is employed as a substrate, another C–X bond (not ortho) remains intact during the reaction. Mechanistic studies revealed that the key to success of this reaction is to generate diboron-bridged five-membered ring as a transition state, in which the diboron-bridged five-membered ring and the benzene ring in the transition state are perpendicular to each other owing to steric repulsion by the iodine atom at the ortho-position. This chemoselectivity is suitable for the synthesis of borylated building blocks.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"53 14","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135869650","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 Practical Synthetic Method for Clinical Candidate 3-(2-{3-[(2,4-Diamino-6-ethylpyrimidin-5-yl)oxy]propoxy} phenyl)propanoic acid (P218) and Its Hydroxylated Metabolites 临床候选3-(2-{3-[(2,4-二氨基-6-乙基嘧啶-5-基)氧]丙氧基}苯基)丙酸(P218)及其羟基化代谢物的实用合成方法的建立
4区 化学
Synthesis-Stuttgart Pub Date : 2023-10-30 DOI: 10.1055/s-0042-1751502
Nitipol Srimongkolpithak, Onanong Vorasin, Tanawat Phumjan, Siriporn Saepua, Daniel Iwaniuk, Sumalee Kamchonwongpaisan, Yongyuth Yuthavong, Chawanee Thongpanchang
{"title":"Development of a Practical Synthetic Method for Clinical Candidate 3-(2-{3-[(2,4-Diamino-6-ethylpyrimidin-5-yl)oxy]propoxy} phenyl)propanoic acid (P218) and Its Hydroxylated Metabolites","authors":"Nitipol Srimongkolpithak, Onanong Vorasin, Tanawat Phumjan, Siriporn Saepua, Daniel Iwaniuk, Sumalee Kamchonwongpaisan, Yongyuth Yuthavong, Chawanee Thongpanchang","doi":"10.1055/s-0042-1751502","DOIUrl":"https://doi.org/10.1055/s-0042-1751502","url":null,"abstract":"Abstract 3-(2-{3-[(2,4-Diamino-6-ethylpyrimidin-5-yl)oxy]propoxy}phenyl)propanoic acid, known as P218, has demonstrated great potency and safety in preclinical and human studies. However, the previous synthetic methods for P218 gave low yields and required hazardous reagents and challenging procedures. In this study, we have successfully developed a decagram-scale synthetic route for P218 with practical and scalable methods for large-scale production. Furthermore, this is also a first report of a novel synthetic approach for P218-OH, a hydroxylated metabolite of P218, by modification of our discovery route. Our synthetic procedures for P218 and P218-OH are a significant advancement in drug development processes, including manufacturing processes and drug metabolism studies.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"326 ","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136019317","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
Linked PDF of Table of Contents 链接的PDF目录
4区 化学
Synthesis-Stuttgart Pub Date : 2023-10-30 DOI: 10.1055/s-0040-1720097
{"title":"Linked PDF of Table of Contents","authors":"","doi":"10.1055/s-0040-1720097","DOIUrl":"https://doi.org/10.1055/s-0040-1720097","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":"182 ","pages":"0"},"PeriodicalIF":0.0,"publicationDate":"2023-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"136102384","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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