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Asymmetric one-pot synthesis of trans-stilbene oxide via desymmetrizing monosulfonylation of meso-hydrobenzoin catalyzed by a chiral bisoxazoline–copper (II) complex
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155435
Kenji Yatsuzuka, Midori Kawasaki, Ryuichi Shirai
{"title":"Asymmetric one-pot synthesis of trans-stilbene oxide via desymmetrizing monosulfonylation of meso-hydrobenzoin catalyzed by a chiral bisoxazoline–copper (II) complex","authors":"Kenji Yatsuzuka,&nbsp;Midori Kawasaki,&nbsp;Ryuichi Shirai","doi":"10.1016/j.tetlet.2024.155435","DOIUrl":"10.1016/j.tetlet.2024.155435","url":null,"abstract":"<div><div>Chiral stilbene oxides are useful and versatile intermediates for the synthesis of chiral ligands for asymmetric catalysis, chiral auxiliaries for diastereoselective transformations, and precursors for chiral building blocks of many compounds. We achieved the enantioselective desymmetric tosylation of <em>meso</em>-hydrobenzoin catalyzed by a chiral ligand–CuCl<sub>2</sub> complex followed by base promoted intramolecular cyclization to furnish <em>trans</em>-stilbene oxide in high yield with excellent enantioselectivity up to 99 %ee in a one-pot operation. This simple transformation offers the most feasible and promising option for the asymmetric synthesis of stilbene oxides with high optical purity.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155435"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159575","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
Unified synthesis of DSPC and PSPC: Chemical entities of hydrogenated soy L-α-phosphatidylcholine (HSPC), a key component of liposomal drug formulations
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155424
Pallavi Rao, Madhavachary Rudrakshula, Rajendar Potham, Rahul Varma Katari, Vishnuvardhana Vema Reddy Eda, Saikat Sen, Srinivas Oruganti
{"title":"Unified synthesis of DSPC and PSPC: Chemical entities of hydrogenated soy L-α-phosphatidylcholine (HSPC), a key component of liposomal drug formulations","authors":"Pallavi Rao,&nbsp;Madhavachary Rudrakshula,&nbsp;Rajendar Potham,&nbsp;Rahul Varma Katari,&nbsp;Vishnuvardhana Vema Reddy Eda,&nbsp;Saikat Sen,&nbsp;Srinivas Oruganti","doi":"10.1016/j.tetlet.2024.155424","DOIUrl":"10.1016/j.tetlet.2024.155424","url":null,"abstract":"<div><div>A simple, unified and scalable strategy, emanating from the readily available chiral pool <span>d</span>-solketal, has been employed to obtain the enantiomerically pure components of hydrogenated soy L-α-phosphatidylcholine (HSPC), namely distearoyl phosphatidylcholine (DSPC) and 1-palmitoyl-2-stearoyl-phosphatidylcholine (PSPC). HSPC is obtained by hydrogenating naturally occurring soy L-α-lecithin; this affords a glycerophospholipid mixture containing C-16 (minor) or C-18 (major) fatty acid chain at <em>sn</em>-1, C-18 chain at <em>sn</em>-2 position and phosphatidylcholine at <em>sn</em>-3 position. HSPC already has numerous applications as an excipient and essential component in many FDA approved liposomal drug formulations such as Doxil® (doxorubicin HCl liposome injection) and AmBisome® (amphotericin B liposome injection). However, there is increasing interest in uncovering the potential individual applications of its components, DSPC and PSPC, too. In this context, the current synthesis offers a strategy to have a ready bespoke access to multi-gram quantities of DSPC and PSPC (in particular) that does not rely on tedious separation of the components of HSPC.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155424"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159666","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
O-Alkylation of hydroxypyridines and derivatives via transient alkyl diazonium species
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155396
Guillaume Reynard , Calvine Lai , Emna Azek , Hélène Lebel
{"title":"O-Alkylation of hydroxypyridines and derivatives via transient alkyl diazonium species","authors":"Guillaume Reynard ,&nbsp;Calvine Lai ,&nbsp;Emna Azek ,&nbsp;Hélène Lebel","doi":"10.1016/j.tetlet.2024.155396","DOIUrl":"10.1016/j.tetlet.2024.155396","url":null,"abstract":"<div><div>Diazotisation of amines with a nitrite reagent was performed in the presence of hydroxy-pyridines and derivatives to give the alkylation products. The <em>O</em>-alkylation product was isolated from 2-, 3-, 4-hydroxypyridines, 2-hydroxyquinoline and 2-hydroxypyrimidines. In the case of 2-hydropyridines, the <em>N</em>-alkylation product was also observed, with the <em>O</em>-alkylation product being favoured. The reaction conditions were compatible with a variety of functional groups, and namely amino alcohols were successfully reacted to afford hydroxy-substituted products. The distinctive reactivity of dinitrites in comparison to mononitrites is also addressed.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155396"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143160319","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
Hydroarylative cyclization of enynes with aromatic ketones catalyzed by a low-valent iron-phosphine complex
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155409
Yoichi Kitazawa , Takuya Kochi , Fumitoshi Kakiuchi
{"title":"Hydroarylative cyclization of enynes with aromatic ketones catalyzed by a low-valent iron-phosphine complex","authors":"Yoichi Kitazawa ,&nbsp;Takuya Kochi ,&nbsp;Fumitoshi Kakiuchi","doi":"10.1016/j.tetlet.2024.155409","DOIUrl":"10.1016/j.tetlet.2024.155409","url":null,"abstract":"<div><div>We report here an iron-catalyzed C<img>H functionalization of aromatic ketones via cyclization of enynes. The reaction is applicable to a variety of aromatic ketones and enables regioselective introduction of a hydrogen atom and an aryl group at the alkyne moiety and the olefin moiety, respectively.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155409"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143127949","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
Ambient temperature activation of diaryliodonium salts: Atom-economic route towards the ex-situ metal-free synthesis of N-methyldiarylamine
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155436
Dhanashri A. Sable, Anant R. Kapdi
{"title":"Ambient temperature activation of diaryliodonium salts: Atom-economic route towards the ex-situ metal-free synthesis of N-methyldiarylamine","authors":"Dhanashri A. Sable,&nbsp;Anant R. Kapdi","doi":"10.1016/j.tetlet.2024.155436","DOIUrl":"10.1016/j.tetlet.2024.155436","url":null,"abstract":"<div><div>An atom economic route for the synthesis of <em>N</em>-methylarylamines via the ambient temperature activation of diaryliodonium salts using an ex-situ generated HNMe<sub>2</sub> has been disclosed and a scale-up reaction was also performed to demonstrate the scalability of the developed protocol.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155436"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159576","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
Silver-catalyzed regioselective synthesis of (E)-vinyl sulfones from nitroolefins and thiophenols
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155425
Kaiyang Zhou , Xinyi Wang , Can Wang , Yunfeng Chen
{"title":"Silver-catalyzed regioselective synthesis of (E)-vinyl sulfones from nitroolefins and thiophenols","authors":"Kaiyang Zhou ,&nbsp;Xinyi Wang ,&nbsp;Can Wang ,&nbsp;Yunfeng Chen","doi":"10.1016/j.tetlet.2024.155425","DOIUrl":"10.1016/j.tetlet.2024.155425","url":null,"abstract":"<div><div>An efficient silver-catalyzed synthesis of (<em>E</em>)-vinyl sulfones was developed by denitrative radical cross-coupling of readily available thiophenols and nitroolefins. This reaction is initiated by generation of a thiyl radical or a sulfonyl radical from the thiophenol.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155425"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159586","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
Cyclocondensation of o-aminophenols with α-ketothioesters in acidic media: A facile synthesis of 2-acylbenzoxazoles
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155418
Kumar Kavya , Mallesha Nayak Sahana , Toreshettahally R. Swaroop , Bilagumba T. Sridhar , Kempegowda Mantelingu
{"title":"Cyclocondensation of o-aminophenols with α-ketothioesters in acidic media: A facile synthesis of 2-acylbenzoxazoles","authors":"Kumar Kavya ,&nbsp;Mallesha Nayak Sahana ,&nbsp;Toreshettahally R. Swaroop ,&nbsp;Bilagumba T. Sridhar ,&nbsp;Kempegowda Mantelingu","doi":"10.1016/j.tetlet.2024.155418","DOIUrl":"10.1016/j.tetlet.2024.155418","url":null,"abstract":"<div><div>We herein report the cyclocondensation of o-aminophenols with α-ketothioesters in acidic media for the highly regioselective synthesis of 2-acylbenzoxazoles in DMF at 80 °C. The generality of the reaction was demonstrated by using various o-aminophenols and α-ketothioesters bearing electron donating and electron withdrawing groups. In the absence and catalytic amount of acid, isomeric mixture of products: benzoxazoles and benzo[b][1,4]oxazin-2-ones were observed. Notably, in the presence of equivalent amount of acid, exclusively and regioselectively benzoxazoles are formed. The probable mechanism of formation of benzoxazoles is also presented.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155418"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159580","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
Biocatalytic synthesis of β-carboline analogues with anti-myocardial fibrosis effect using the amide bond synthetase MarA
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155410
Qing Shi , Jing-Jing Liu , Lu-Jia Wang , Hui Mao , Yu-Yang Zhang , Bo Wei , Shuang-Jun Lin , Ai-Jun Hou
{"title":"Biocatalytic synthesis of β-carboline analogues with anti-myocardial fibrosis effect using the amide bond synthetase MarA","authors":"Qing Shi ,&nbsp;Jing-Jing Liu ,&nbsp;Lu-Jia Wang ,&nbsp;Hui Mao ,&nbsp;Yu-Yang Zhang ,&nbsp;Bo Wei ,&nbsp;Shuang-Jun Lin ,&nbsp;Ai-Jun Hou","doi":"10.1016/j.tetlet.2024.155410","DOIUrl":"10.1016/j.tetlet.2024.155410","url":null,"abstract":"<div><div>The β-carboline scaffold and amide bond have great potential for drug discovery as consisting in many marketed pharmaceuticals and drug candidates. Compared to the chemical method, enzymatic synthesis of amide with nontoxicity and mild reaction conditions has received great attention. In this study, the amide bond synthetase MarA was characterized, and a series of novel amide-containing β-carboline analogues were synthesized by MarA-catalyst. Compound <strong>5b</strong> having fluorine substitution, and compound <strong>5n</strong> possessing an <em>N</em>-methyl substituent, showed excellent anti-myocardial fibrosis effects, which were found to be superior to the positive control drug, captopril. Our study provides MarA as a new green biocatalytic strategy for the synthesis of new β-carboline analogues with anti-fibrotic properties.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155410"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159581","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
Construction of functionalized naphtho[2,1-c]chromene scaffolds by Diels-Alder reaction using benzyne as dienophiles
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155430
Chuanlin Lan, Yingyi Wang, Feng Sha, Xinyan Wu, Yian Cui, Yi Zheng
{"title":"Construction of functionalized naphtho[2,1-c]chromene scaffolds by Diels-Alder reaction using benzyne as dienophiles","authors":"Chuanlin Lan,&nbsp;Yingyi Wang,&nbsp;Feng Sha,&nbsp;Xinyan Wu,&nbsp;Yian Cui,&nbsp;Yi Zheng","doi":"10.1016/j.tetlet.2024.155430","DOIUrl":"10.1016/j.tetlet.2024.155430","url":null,"abstract":"<div><div>In this study, a direct synthetic methodology for the construction of dihydronaphtho[2,1-<em>c</em>]chromene scaffold derivatives has been developed. Via the benzyne-participating Diels-Alder route, the naphtho[2,1-<em>c</em>]chromene skeleton possessing promising biological activity could be efficiently furnished under mild conditions.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155430"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159587","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
Stereocontrolled synthesis of an α–monosubstituted α–amino acid derivative from a Ugi reaction product
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-27 DOI: 10.1016/j.tetlet.2025.155488
Shuntaro Tsukamoto, Yuki Suzuki, Masato Oikawa
{"title":"Stereocontrolled synthesis of an α–monosubstituted α–amino acid derivative from a Ugi reaction product","authors":"Shuntaro Tsukamoto,&nbsp;Yuki Suzuki,&nbsp;Masato Oikawa","doi":"10.1016/j.tetlet.2025.155488","DOIUrl":"10.1016/j.tetlet.2025.155488","url":null,"abstract":"<div><div>We report herein an unprecedented concept for an enantiospecific synthetic strategy for α–amino acid derivatives starting from Ugi four-component coupling reaction employing chiral amine, via a chiral morpholinone intermediate. This concept was proven by the successful synthesis of (<em>S</em>)–<em>N</em>–Ac–<em>tert</em>–leucine.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155488"},"PeriodicalIF":1.5,"publicationDate":"2025-01-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150501","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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