{"title":"Linked PDF of Table of Contents","authors":"","doi":"10.1055/s-0040-1720083","DOIUrl":"https://doi.org/10.1055/s-0040-1720083","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-08-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135065281","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":"SYNFORM ISSUE 2023/9","authors":"M. Zanda","doi":"10.1055/s-0040-1720607","DOIUrl":"https://doi.org/10.1055/s-0040-1720607","url":null,"abstract":"INTERVIEW SYNFORM You are a leading researcher in the field of organic synthesis. Could you tell us more about the importance of that field and your current research activities? Prof. T. S. Lee Since three scientists were awarded the No bel prize on “Electrically conductive plastic” in 2000, tons of organic materials have been developed for electronics and pho to nics. As a result, we can see various information through OLED-based smart phones and laptops. Electro-and photo-active organic materials are synthesized based on organic synthetic techniques, including many coupling reactions like Suzuki, Stille, Yamamoto, and Heck reactions. SYNFORM Please comment on your role as a member of the Associate Board of SynOpen. Prof. T. S. Lee My role is to assist with the rapid publication of high-graded papers. SYNFORM Could you tell us something about yourself outside the lab, such as your hobbies or extra-work interests? Prof. T. S. Lee My hobbies include running, golfing, boxing, watching TV, and reading.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2023-08-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"77785565","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":"Synthesis and Immunological Evaluation of Escherichia coli O1- Derived Oligosaccharide–Protein Conjugates toward Avian Pathogenic Escherichia coli O1 Vaccine Development","authors":"Katsunori Seki, Takumi Makikawa, Kazunobu Toshima, Daisuke Takahashi","doi":"10.1055/a-2152-0255","DOIUrl":"https://doi.org/10.1055/a-2152-0255","url":null,"abstract":"Abstract Avian pathogenic Escherichia coli O1 (APEC O1) is a pathogenic bacterium that causes significant economic losses in the poultry industry and raises concerns about zoonotic infections. The development of effective vaccines against APEC O1 is essential due to antibiotic resistance and the potential for severe symptoms in both chickens and humans. In this context, we have been focusing on the O1A, O1B, and O1C antigen structures derived from E. coli O1 lipopolysaccharide (LPS). In this study, the first synthesis of the pentasaccharide repeating units of the O1B and O1C antigens was successfully achieved. The synthesis and immunological evaluation of their conjugates with bovine serum albumin (BSA) were conducted. Only the O1A-pentasaccharide structure is a glycotope candidate for APEC O1. Keyhole limpet hemocyanin (KLH)–O1A-pentasaccharide conjugate was also synthesized, and its immunogenicity was evaluated by the ELISA assay. The efficient production of antibodies capable of binding to both APEC O1 LPS and the O1A-pentasaccharide structure was observed, indicating that O1A-pentasaccharide is a promising vaccine candidate against APEC O1.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":0.0,"publicationDate":"2023-08-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"135491942","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}
Manpreet Singh, V. Vaishali, D. Deepika, J. Jyoti, Shubham Sharma, Naveen Banyal, Prashant Kumar, Bharti Budhalakoti, C. Malakar, Virender Singh
{"title":"Erratum - Transition-Metal-Free Cascade C–N Bond Formation: An Effective Strategy for the Synthesis of β-Carboline N-Fused Imidazolium Acetates and Estimation of their Light-Emitting Properties","authors":"Manpreet Singh, V. Vaishali, D. Deepika, J. Jyoti, Shubham Sharma, Naveen Banyal, Prashant Kumar, Bharti Budhalakoti, C. Malakar, Virender Singh","doi":"10.1055/s-0040-1720082","DOIUrl":"https://doi.org/10.1055/s-0040-1720082","url":null,"abstract":"","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2023-08-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"89882744","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}
M. Ordóñez, Rubén Oswaldo Argüello-Velasco, Teodoro Miranda-Blancas, Iván Romero-Estudillo, Victoria Labastida-Galván
{"title":"First Stereoselective Synthesis of Diethyl cis - and trans -(4-Hydroxy-1,2,3,4-tetrahydroquinolin-2-yl)phosphonates and Ethyl Phenylphosphinates from Quinolin-4(1 H )-one","authors":"M. Ordóñez, Rubén Oswaldo Argüello-Velasco, Teodoro Miranda-Blancas, Iván Romero-Estudillo, Victoria Labastida-Galván","doi":"10.1055/a-2164-2075","DOIUrl":"https://doi.org/10.1055/a-2164-2075","url":null,"abstract":"We report here a practical method for the first stereoselective synthesis of novel diethyl cis- and trans-(4-hydroxy-1,2,3,4-tetrahydro-quinolin-2-yl)phosphonates, as well as the ethyl cis- and trans-(4-hydroxy-1,2,3,4-tetrahydroquinolin-2-yl)phenylphosphinates. The main feature of this method involves the regioselective 1,4-phosponylation to N-Cbz quinolin-4(1H)-one using diethyl phosphite or ethyl phenylphosphinate followed by the high diastereoselective reduction, to give the cis stereoisomers as favored products, which through the Mitsunobu reaction were converted into trans stereoisomers. Cleavage of N-Cbz bond under hydrogenolysis, gave the target heterocyclic α-aminophosphonates and α-aminophosphinates.","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2023-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"91166608","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":"Electrochemical Organic Synthesis","authors":"Hai‐Chao Xu","doi":"10.1055/s-0040-1720081","DOIUrl":"https://doi.org/10.1055/s-0040-1720081","url":null,"abstract":"The potential of electrochemical organic synthesis in achieving sustainable and efficient chemical syntheses, while offering unique reactivity and selectivity, makes it a promising avenue for addressing the challenges in synthetic organic chemistry. The past two decades have witnessed a remarkable advancement in organic electrochemistry, primarily due to the influx of passionate and innovative scientists. These trailblazers, armed with their unique perspectives, are driving the field into uncharted territories, often surpassing the visions of the early pioneers. Their groundbreaking work is carving out new frontiers and making significant scientific impacts, which are aptly highlighted in this special issue. Their pioneering contributions are projected to extend the core foundation of electrochemistry and usher in transformative insights. The articles featured in this special issue on electrochemical organic synthesis are the result of a diverse array of authors hailing from countries across the globe, including Brazil, Canada, China, France, Italy, Japan, Portugal, and the United States. This variety exemplifies the widespread adoption and universal appeal of electrochemistry in the realm of synthetic organic chemistry, confirming its global recognition and relevance within the international scientific community. In this special issue, a selection of review papers vividly illuminates the latest advancements and emerging topics in electrochemical organic synthesis. He, Pan and colleagues explore the evolution of spirocyclic compound construction via electrochemical synthesis strategies since 2000.1 Kong, Cao, and colleagues shed light on recent progress in electro-, photo-, and photoelectrochemical applications of quaternary ammonium salts.2 Qin, Li and co-workers present an indepth review of electrochemical difunctionalization of alkenes.3 Lu and his team delve into transition-metal electrochemical asymmetric catalysis including the recently emerged photoelectrochemical asymmetric catalysis (PEAC).4 Phillips, Pombeiro, and associates encapsulate the power of electrochemistry in catalytic enantioselective synthesis.5 Zhang, Liu, and their team offer a comprehensive summary of electrochemical cascade cyclization reactions used in carbon ring and heterocycle production.6 Mo and his team succinctly overview the latest breakthroughs in high-throughput experimentation technology for electrosynthesis.7 Gui and his team have provided a comprehensive summary of halogen-mediated electrochemical transformations of sulfur-containing compounds.8 Lastly, Chen and his team delve into the fascinating topic of photoelectrochemical cerium catalysis in their detailed review.9 Moreover, an assortment of research papers exhibits the cutting-edge methods and techniques in the field. A notable contribution from Charette, Poisson, Jubault, and their team delineates the synthesis of cyclopropylamines from the corresponding amides through a bromide-mediated, electroinduc","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2023-08-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"87571829","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}
Synthesis-StuttgartPub Date : 2023-08-01Epub Date: 2023-02-02DOI: 10.1055/s-0042-1751413
Jonathan R Scheerer, Ella B Leeth, Jennifer A Sprow
{"title":"Synthesis of Guaipyridine Alkaloids Rupestine M and L by Cycloaddition/Cycloreversion of an Intermediate 1,4-Oxazinone.","authors":"Jonathan R Scheerer, Ella B Leeth, Jennifer A Sprow","doi":"10.1055/s-0042-1751413","DOIUrl":"10.1055/s-0042-1751413","url":null,"abstract":"<p><p>A new method to prepare 1,4-oxazinone intermediates was developed based on aza-conjugate addition of β-amino alcohols to electron-deficient alkyne precursors. A tandem intramolecular cycloaddition/cycloreversion reaction sequence was evaluated, leading to the synthesis of the guaipyridine alkaloid natural products rupestine M and L. Starting from (-)-citronellal and thus a known configuration of the C5 stereocenter, a revised absolute configuration of natural rupestine L is suggested based on optical rotation.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.6,"publicationDate":"2023-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10489027/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"10588037","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}
Synthesis-StuttgartPub Date : 2023-08-01Epub Date: 2022-12-15DOI: 10.1055/s-0042-1751393
Emma C Murphy, Jeffrey S Johnson
{"title":"Simplified Synthesis of an Air-Stable Copper-Complexed Josiphos Ligand via Ugi's Amine: Complete Preparation and Analysis from Ferrocene.","authors":"Emma C Murphy, Jeffrey S Johnson","doi":"10.1055/s-0042-1751393","DOIUrl":"10.1055/s-0042-1751393","url":null,"abstract":"<p><p>Ligands containing ferrocene backbones often feature both planar chirality and asymmetric centers, making them attractive options for asymmetric catalysis. Ugi's amine is a ubiquitous ferrocene-based chiral building block that can be functionalized to form a variety of tunable Josiphos ligands; however, few sources lay out the route from start to finish. Starting from ferrocene, we compile a synthetic route to an air- and moisture-stable copper(I)-Josiphos complex via enantiopure Ugi's amine, providing a potential one-stop shop for the synthesis of a wide range of Josiphos ligands.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.2,"publicationDate":"2023-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10438921/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"10105521","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}
Synthesis-StuttgartPub Date : 2023-08-01Epub Date: 2022-10-12DOI: 10.1055/s-0042-1751362
Yudong Liu, K A Woerpel
{"title":"Uncatalyzed Carbometallation Involving Group 13 Elements: Carboboration and Carboalumination of Alkenes and Alkynes.","authors":"Yudong Liu, K A Woerpel","doi":"10.1055/s-0042-1751362","DOIUrl":"10.1055/s-0042-1751362","url":null,"abstract":"<p><p>Carbometallation of alkenes and alkynes are powerful carbon-carbon bond-forming reactions. The use of compounds containing bonds between carbon and group 13 elements, particularly boron and aluminum, are particularly attractive because of the versatility of subsequent transformations. Uncatalyzed carboboration and carboalumination represent less common classes of reactions. This Short Review discusses uncatalyzed carboboration and carboalumination reactions of alkenes and alkynes, including the reaction design and mechanism.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.2,"publicationDate":"2023-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10795483/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"81871395","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}
Synthesis-StuttgartPub Date : 2023-08-01Epub Date: 2023-04-13DOI: 10.1055/a-2022-1511
Subhradeep Dutta, Kamal Bhatt, Fabian Cuffel, Daniel Seidel
{"title":"Synthesis of Polycyclic Imidazoles via α-C-H/N-H Annulation of Alicyclic Amines.","authors":"Subhradeep Dutta, Kamal Bhatt, Fabian Cuffel, Daniel Seidel","doi":"10.1055/a-2022-1511","DOIUrl":"10.1055/a-2022-1511","url":null,"abstract":"<p><p>Secondary alicyclic amines are converted to their corresponding ring-fused imidazoles in a simple procedure consisting of oxidative imine formation followed by a van Leusen reaction. Amines with an existing α-substituent undergo regioselective ring-fusion at the α'-position. This method was utilized in a synthesis of fadrozole.</p>","PeriodicalId":49451,"journal":{"name":"Synthesis-Stuttgart","volume":null,"pages":null},"PeriodicalIF":2.2,"publicationDate":"2023-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10836336/pdf/","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"72488714","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}