European Journal of Organic Chemistry最新文献_第9页

Ligand‐Free Copper‐Catalyzed Allenylative C‐P Coupling of Propargylic Acetates with H‐Phosphine Oxides 无配体铜催化丙炔乙酸酯与氢膦氧化物的烯丙化C - P偶联

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-06-26 DOI: 10.1002/ejoc.202500514

Shaoqing Liu, Jiawei Liu, Li-Biao Han, Ruwei Shen

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Synthesis of the [6‐5‐5‐3] Tetracyclic Core of Cryptotrione 隐三酮[6‐5‐5‐3]四环核的合成

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-06-26 DOI: 10.1002/ejoc.202500399

Nan Hu, Jun-Ting Liang, Yong-Bin Xie, Chuang-Chuang Li, Yu-Tao He, Ya-Jian Hu

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DMAPO/Boc2O‐Mediated One‐Pot Direct N‐Acylation of Sulfoximines with Carboxylic Acids DMAPO/Boc2O介导的亚砜亚胺与羧酸的一锅直接N酰化反应

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-06-26 DOI: 10.1002/ejoc.202500488

Atsushi Umehara, Sukenao Kawai, Makoto Sasaki

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Rhodium‐Catalyzed (3+3) Cascade Cyclization of Diazobarbiturates with 2H‐Azirines for the Diastereoselective Construction of Spirooxazinopyrimidinediones 铑催化重氮巴比妥酸盐与2H -氮嘧啶的（3+3）级联环化，用于螺恶嗪嘧啶嘧啶二酮的非对映选择性构建

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-06-25 DOI: 10.1002/ejoc.202500551

Hong-Wu Zhao, Yue Zhang, Yu-Hang Mi, Kuo Wang, Zhi-Yu Wang, Jin-Tao Li

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Facilitating the Isolation of Polar Natural Products: Mild 1,1′-Carbonyldiimidazole-Enabled Method for Derivatization of Acids and Alcohols 促进极性天然产物的分离：温和的1,1 ' -羰基二咪唑-激活方法用于酸和醇的衍生化

IF 2.7 3区化学

European Journal of Organic Chemistry Pub Date : 2025-06-25 DOI: 10.1002/ejoc.202500231

Moses M. Mutungi, Curtis C. Ho, Alex C. Bissember, Jason A. Smith

{"title":"Facilitating the Isolation of Polar Natural Products: Mild 1,1′-Carbonyldiimidazole-Enabled Method for Derivatization of Acids and Alcohols","authors":"Moses M. Mutungi, Curtis C. Ho, Alex C. Bissember, Jason A. Smith","doi":"10.1002/ejoc.202500231","DOIUrl":"10.1002/ejoc.202500231","url":null,"abstract":"<p>Many secondary metabolites containing carboxylic acid and alcohol functional groups are highly polar and can be difficult to purify and isolate from complex extracts obtained from natural sources. The conversion of these natural products to their corresponding alkyl esters/carbonates under mild conditions can simplify their purification and isolation. However, traditional derivatization methods have often relied on toxic and/ or corrosive reagents that can also lead to byproduct formation or epimerization in some instances. In this work, 1,1′-carbonyldiimidazole, a relatively inexpensive reagent with inherently low toxicity, is utilized to activate polar natural products containing carboxylic acids and alcohols to enable the formation of less polar species (N-acylimidazoles and N-acyloxymidazoles). These intermediates are readily converted into methyl esters and carbonates by treatment with methanol. It is anticipated that this rather simple and versatile derivatization method can facilitate the efficient isolation of secondary metabolites bearing polar carboxylic acid and alcohol residues.</p>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 28","pages":""},"PeriodicalIF":2.7,"publicationDate":"2025-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202500231","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144488567","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

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Towards the Synthesis of 3,3‐Difluoro Deaminated Sialic Acid (C3DFKDN) 3,3‐二氟脱氨唾液酸（C3DFKDN）的合成

IF 2.8 3区化学

European Journal of Organic Chemistry Pub Date : 2025-06-25 DOI: 10.1002/ejoc.202500456

Lemeng Chao, Tom Wennekes

{"title":"Towards the Synthesis of 3,3‐Difluoro Deaminated Sialic Acid (C3DFKDN)","authors":"Lemeng Chao, Tom Wennekes","doi":"10.1002/ejoc.202500456","DOIUrl":"https://doi.org/10.1002/ejoc.202500456","url":null,"abstract":"2‐Keto‐3‐deoxy‐d‐glycero‐d‐galacto‐nononic acid (KDN) is a nine‐carbon monosaccharide of the sialic acid family. As a deaminated analogue of N‐acetylneuraminic acid (Neu5Ac), KDN features a hydroxyl group at C5 instead of an amine. Although present at low levels in mammalian tissues, KDN is abundant in certain tumor cells and pathogens, making it and its processing enzymes attractive targets for understanding biological functions and developing potential therapeutics. Fluorinated carbohydrate derivatives are widely used to probe and modulate carbohydrate‐active enzymes (CAZymes). Here, we report the first total synthesis of 3,3‐difluoro KDN (C3DFKDN), a novel fluorinated sialic acid derivative and a key intermediate for designing covalent inhibitors and activity‐based probes targeting KDN‐processing enzymes. Introduction of a C3‐difluoro group prevents elimination side reactions common with monofluorinated sialic acid analogues. Two synthetic strategies were explored: (1) coupling a pyranose precursor with a difluorinated alkyne bromide followed by oxidation, and (2) incorporation of a difluoroacetate building block via a Reformatsky‐type reaction. The latter approach proved more effective, affording protected C3DFKDN in an overall yield of 3.7% over 12 steps from methyl α‐d‐mannopyranoside. This work establishes methodology for the synthesis of C3‐difluorinated sialic acids and provides a foundation for developing fluorinated probes and inhibitors of KDN‐related enzymatic pathways.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"630 1","pages":""},"PeriodicalIF":2.8,"publicationDate":"2025-06-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144488569","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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

Electrochemically Promoted Amination of Pyrido[2,3‐d]pyrimidin‐7‐ones: Efficient Synthesis of Palbociclib Derivatives 电化学促进吡啶[2,3-d]嘧啶-7- 1胺化：帕博西尼衍生物的高效合成

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-06-24 DOI: 10.1002/ejoc.202500259

Dong Wang , Lixi Zhang , Jiabin Shen , Pengfei Zhang , Chao Shen , Qing Zhu

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Manganese‐Catalyzed Synthesis of Tetrahydropyridines via Borrowing Hydrogen Strategy 锰催化借氢合成四氢吡啶

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-06-24 DOI: 10.1002/ejoc.202500269

Feixiang Sun , Weiping Liu

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Electrochemical Fluorination of Proline Derivatives 脯氨酸衍生物的电化学氟化

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-06-24 DOI: 10.1002/ejoc.202500264

Patrick Ryan , Dhananjay Bhattacherjee , Thomas Wirth , Luke Hunter , Giancarlo Pascali

{"title":"Electrochemical Fluorination of Proline Derivatives","authors":"Patrick Ryan , Dhananjay Bhattacherjee , Thomas Wirth , Luke Hunter , Giancarlo Pascali","doi":"10.1002/ejoc.202500264","DOIUrl":"10.1002/ejoc.202500264","url":null,"abstract":"<div><div>The introduction of a fluorine into aliphatic substituents of lead candidates can impart unique structural characteristics that allow fine tuning of drug interactions; therefore, mild, specific, or late‐stage fluorination procedures are of growing interest in medicinal chemistry, with the potential to be applied in F‐18 radiochemistry. In this work, we demonstrate the feasibility of “reagent‐less” electrochemical fluorination leading to mono‐ and gem‐difluorinated proline cores featured in important fibroblast‐activating protein inhibitors. Our study highlights the importance of using the appropriate activator substituents for allowing the process, the impact of different reaction parameters, and characterizes the various byproducts that are generated in the reaction. We have tested the reaction using a commercially available batch system and flow apparatus, achieving maximum yields of >90% (batch) for mono‐ and of 6% (batch) and 9% (flow) for the gem‐difluorinated proline model. These proof‐of‐concept results indicate that the flow approach is more efficient, but that different activating substituents will be needed to achieve higher yields.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 24","pages":"Article e202500264"},"PeriodicalIF":2.5,"publicationDate":"2025-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144104246","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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

Gold(I)‐Catalyzed Allylation and Tandem Allylation–Cycloisomerization of Stannylated Propargyl Acetates with Allylsilanes 金(I)催化丙烯基硅烷与丙烯基乙酸酯烯丙基化及串联烯丙基环异构化反应

IF 2.5 3区化学

European Journal of Organic Chemistry Pub Date : 2025-06-24 DOI: 10.1002/ejoc.202500253

Nene Murata , Sota Akima , Syed R. Hussaini , Yoshikazu Horino

{"title":"Gold(I)‐Catalyzed Allylation and Tandem Allylation–Cycloisomerization of Stannylated Propargyl Acetates with Allylsilanes","authors":"Nene Murata , Sota Akima , Syed R. Hussaini , Yoshikazu Horino","doi":"10.1002/ejoc.202500253","DOIUrl":"10.1002/ejoc.202500253","url":null,"abstract":"<div><div>Bicyclo[3.1.0]hex‐2‐enes, synthesized by the cycloisomerization of 1,5‐enynes, serve as key scaffolds in various natural products. Gold(I)‐catalyzed cycloisomerization of 1,5‐enynes is an efficient route to bicyclo[3.1.0]hex‐2‐enes. However, gold(I)‐catalyzed 1,5‐enyne synthesis, particularly with a terminal alkyne, has not yet been fully explored. This study presents a mild and general method for the gold(I)‐catalyzed allylation and tandem allylation–cycloisomerization of stannylated propargyl acetates with allylsilanes, yielding 1,5‐enynes with terminal alkyne moiety and bicyclo[3.1.0]hex‐2‐enes. The catalytic system ((4‐MeOC<sub>6</sub>H<sub>4</sub>)<sub>3</sub>PAuCl/AgSbF<sub>6</sub>) enabled the efficient synthesis of 1,5‐enynes with good to high yields and regioselectivities. In addition, gold(I)‐catalyzed tandem allylation–cycloisomerization using (JohnPhos)Au(MeCN)SbF<sub>6</sub> afforded bicyclo[3.1.0]hex‐2‐enes with high regiocontrol. Stannylated propargyl acetates proved crucial in enhancing selectivity for both product classes.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 24","pages":"Article e202500253"},"PeriodicalIF":2.5,"publicationDate":"2025-06-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143767160","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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