SynlettPub Date : 2024-04-18DOI: 10.1055/a-2301-2358
Jiawei Li, Runing Gao, Tianhui Hao, Tiehai Li
{"title":"Stereocontrolled Synthesis of a Heptose- and Kdo-Containing Common Inner-Core Trisaccharide of Lipopolysaccharides from Multiple Pathogenic Bacteria","authors":"Jiawei Li, Runing Gao, Tianhui Hao, Tiehai Li","doi":"10.1055/a-2301-2358","DOIUrl":"https://doi.org/10.1055/a-2301-2358","url":null,"abstract":"<p>Lipopolysaccharides (LPSs) are major virulence determinants in Gram-negative bacteria and are responsible for many pathophysiological processes during bacterial infections. However, the accessibility of LPS-associated oligosaccharides for infectious mechanism study and vaccine development remains challenging. We report an efficient stereocontrolled approach for the synthesis of a common inner-core trisaccharide containing difficult-to-access, rare, higher-carbon sugars: a heptose (Hep) and 3-deoxy-α-<sc>d</sc>-<i>manno</i>-oct-2-ulosonic acid (Kdo). Key features include comprehensive elaboration of a practical synthesis of versatile Hep and Kdo building blocks, and stereoselective assembly of an inner-core trisaccharide from multiple pathogenic bacteria.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"28 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140629774","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}
SynlettPub Date : 2024-04-15DOI: 10.1055/s-0043-1763751
Yaroslav O. Chuchvera, Valentyna Tararina, Inna Chuchvera, Eugeniy N. Ostapchuk, Maria V. Popova, Svitlana V. Shishkina, Yulian M. Volovenko, Alexey V. Dobrydnev
{"title":"Synthesis of α-Phenyl β-Enamino γ-Sultims: the New Horizon of the CSIC Reaction","authors":"Yaroslav O. Chuchvera, Valentyna Tararina, Inna Chuchvera, Eugeniy N. Ostapchuk, Maria V. Popova, Svitlana V. Shishkina, Yulian M. Volovenko, Alexey V. Dobrydnev","doi":"10.1055/s-0043-1763751","DOIUrl":"https://doi.org/10.1055/s-0043-1763751","url":null,"abstract":"<p>Herein, we report the novel strategy for the synthesis of 4-enamino-5-phenyl-2,3-dihydroisothiazole 1-oxides (in other words α-phenyl β-enamino γ-sultims) based on the CSIC reaction. Particularly, readily available α-amino nitriles (the Strecker products) reacted with benzyl sulfinyl chloride to give the corresponding sulfinamides, which upon treatment with excess of LiHMDS converted into the target α-phenyl β-enamino γ-sultims. The method works well and tolerates strained 3- and 4-membered spirocyclic substituents. A preliminary <i>in silico</i> study indicated that the γ-sultim scaffold can be considered a promising pharmacophore template.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"58 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-04-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140560586","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}
SynlettPub Date : 2024-04-09DOI: 10.1055/a-2293-3370
Xianming Zhang, Zhenqiang Zhang, Zhuangping Zhan
{"title":"Visible-Light-Catalyzed Regioselective Arylcarboxylation of Allenes with CO2","authors":"Xianming Zhang, Zhenqiang Zhang, Zhuangping Zhan","doi":"10.1055/a-2293-3370","DOIUrl":"https://doi.org/10.1055/a-2293-3370","url":null,"abstract":"<p>A visible-light-catalyzed arylcarboxylation of allenes with CO<sub>2</sub> was developed using [Ir(ppy)<sub>2</sub>(dtbbpy)]PF<sub>6</sub> (ppy = 2-phenylpyridine; dtbbpy = 4,4′-di-<i>tert</i>-butyl-2,2′-bipyridine) as a photocatalyst to synthesis β-aryl β,γ-unsaturated carboxylic acids. This multicomponent protocol proceeds in an atom-economical way with exclusive regioselectivity. Preliminary mechanistic experiments suggested that allylic carbanion species are the key intermediates.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"48 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140560671","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}
{"title":"Expedient Synthesis of gem-CF2-2H-Thiophenes from Enaminothiones","authors":"Xinyu Zhang, Xuheng Zhang, Rui Fu, Zhengyu Zhang, Yaojia Jiang","doi":"10.1055/s-0043-1763749","DOIUrl":"https://doi.org/10.1055/s-0043-1763749","url":null,"abstract":"<p>An expedient and easy-to-handle synthetic platform has been established for the constructing of 2<i>H</i>-thiophenes carrying fluorine atoms through [4+1] cyclization of enaminothiones with fluorinated carbene precursors. This simple reaction system is well compatible with a wide range of substrates under completely metal-free conditions. The resulting 2<i>H</i>-thiophenes can undergo further late-stage modifications to yield a wide range of fluorine-substituted heterocycles.</p>","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"33 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140560602","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}
{"title":"Rapid Cyclic Acetal and Cyclic Ketal Synthesis Assisted by a Rotary Evaporator","authors":"Fuyao Jiang, Yinzhe Chen, Weiding Wang, Qian Zhang","doi":"10.1055/a-2293-3243","DOIUrl":"https://doi.org/10.1055/a-2293-3243","url":null,"abstract":"<p>Herein, we present a rapid and efficient method for synthesizing cyclic acetals and ketals utilizing a rotary evaporator. Unlike the conventional Dean–Stark dehydration process, which typically demands extended reaction times and copious amounts of organic solvents, our approach affords the synthesis of cyclic acetals and ketals with varying ring sizes in 30 min while using minimal quantities of dimethyl sulfoxide as the solvent. This innovative protocol features high yields, fast reactions, easy operation, and broad substrate applicability.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"5 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140560588","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}
SynlettPub Date : 2024-04-04DOI: 10.1055/a-2287-9391
Jun Nagaki, Tomoko Kawasaki-Takasuka, Keiji Mori
{"title":"(n+3)-Cyclization for the Formation of Benzo[7]annulene Derivatives via a [1,4]-Hydride Shift: A Novel Cyclization Mode Involving an Internal Redox Reaction","authors":"Jun Nagaki, Tomoko Kawasaki-Takasuka, Keiji Mori","doi":"10.1055/a-2287-9391","DOIUrl":"https://doi.org/10.1055/a-2287-9391","url":null,"abstract":"<p>We report a unique synthetic route to benzo[7]annulene derivatives. When benzylidene malonates having a 1-(<i>N</i>,<i>N</i>-dialkylamino)alkyl group at the <i>ortho</i>-position are treated with a stoichiometric amount of M(OTf)<sub>3</sub> (M = Sc, Yb, Gd), three transformations ([1,4]-hydride shift/isomerization into an enamine/intramolecular Stork enamine acylation) proceed sequentially to afford various benzo[7]annulene derivatives in moderate chemical yields. To our knowledge, the present reaction is the first example of an internal redox reaction involving a [1,<i>n</i>]-hydride shift/(<i>n</i>+3)-cyclization process.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"45 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140560668","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}
SynlettPub Date : 2024-04-03DOI: 10.1055/a-2290-1682
{"title":"Synthesis of Fused-Ring Pyrrolizine Derivatives via a Copper-Catalyzed Radical Cascade Cyclization","authors":"","doi":"10.1055/a-2290-1682","DOIUrl":"https://doi.org/10.1055/a-2290-1682","url":null,"abstract":"Herein, an atom-economic method for the synthesis of fused-ring pyrrolizine derivatives by a cycloaddition reaction of easily accessible N-substituted pyrrole-2-carboxaldehydes with N-substituted maleimides in the presence of di-tert-butyl peroxide has been successfully developed. A total of 23 compounds were obtained by using this method, with a maximum yield of 72%, providing a practical and efficient method for the synthesis of tricyclic pyrrolizine frameworks.","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"74 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140560585","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}
SynlettPub Date : 2024-04-03DOI: 10.1055/a-2290-0894
Yun-Fan Li, Cun Yang, Yu-Ting Xi, Qitao Tan, Chang-Hua Ding, Bin Xu
{"title":"Palladium-Catalyzed Asymmetric [3+2] Cycloaddition Reaction of Vinyl Cyclopropane with Electron-Deficient Dienes","authors":"Yun-Fan Li, Cun Yang, Yu-Ting Xi, Qitao Tan, Chang-Hua Ding, Bin Xu","doi":"10.1055/a-2290-0894","DOIUrl":"https://doi.org/10.1055/a-2290-0894","url":null,"abstract":"<p>Palladium-catalyzed asymmetric [3+2] cycloaddition reaction of vinyl cyclopropane and electron-deficient dienes was realized. The cycloaddition reaction proceeded regioselectively on the distant C=C double bond of electron-deficient dienes, and was mainly controlled by the steric hindrance of the 5-substituent of electron-deficient dienes. Chiral multi-substituted cyclopentanes bearing three functional groups (monosubstituted alkene, conjugated ester, and cyano) and three continuous stereocenters were obtained in moderate to high yields, diastereoselectivities, and enantioselectivities.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"20 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140560583","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}
SynlettPub Date : 2024-04-02DOI: 10.1055/a-2268-4386
Jan Nowak, Michał Tryniszewski, Michał Barbasiewicz
{"title":"Are β-Lactones Involved in Carbon-Based Olefination Reactions?","authors":"Jan Nowak, Michał Tryniszewski, Michał Barbasiewicz","doi":"10.1055/a-2268-4386","DOIUrl":"https://doi.org/10.1055/a-2268-4386","url":null,"abstract":"<p>Heteroatom-based olefinating reagents (e.g., organic phosphonates, sulfonates, etc.) are used to transform carbonyl compounds into alkenes, and their mechanism of action involves aldol-type addition, cyclization, and fragmentation of four-membered ring intermediates. We have developed an analogous process using ethyl 1,1,1,3,3,3-hexafluoroisopropyl methylmalonate, which converts electrophilic aryl aldehydes into α-methylcinnamates in up to 70% yield. The reaction plausibly proceeds through the formation of β-lactone that spontaneously decarboxylates under the reaction conditions. The results shed light on the Knoevenagel–Doebner olefination, for which decarboxylative <i>anti</i>-fragmentation of aldol-type adducts is usually considered.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"56 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140560513","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}
SynlettPub Date : 2024-04-02DOI: 10.1055/a-2288-3074
Steffen Skowaisa, Edgar Haak
{"title":"Regiocontrolled Ruthenium-Catalyzed Isomerization of Propargyl Alcohols","authors":"Steffen Skowaisa, Edgar Haak","doi":"10.1055/a-2288-3074","DOIUrl":"https://doi.org/10.1055/a-2288-3074","url":null,"abstract":"<p>A diaminocyclopentadienone ruthenium complex allows control of regioselectivity in the ruthenium-catalyzed isomerization of propargyl alcohols through the choice of additive. Thereby, both products of the Meyer–Schuster rearrangement and redox isomerization products are selectively accessible. In the presence of hydroxylamine-<i>O</i>-sulfonic acid, unsaturated nitriles are formed instead. The ruthenium catalyst is readily available and stable to moisture, air, and acidic conditions.</p> ","PeriodicalId":22319,"journal":{"name":"Synlett","volume":"167 1","pages":""},"PeriodicalIF":2.0,"publicationDate":"2024-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"140560593","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}