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Three unusual 4-oxo-20-nor-taxanes from the cell cultures of Taxus × media
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-13 DOI: 10.1016/j.tetlet.2025.155503
Yuxin Wang , Changkang Li , Songyang Sui, Jimei Liu, Jungui Dai
{"title":"Three unusual 4-oxo-20-nor-taxanes from the cell cultures of Taxus × media","authors":"Yuxin Wang ,&nbsp;Changkang Li ,&nbsp;Songyang Sui,&nbsp;Jimei Liu,&nbsp;Jungui Dai","doi":"10.1016/j.tetlet.2025.155503","DOIUrl":"10.1016/j.tetlet.2025.155503","url":null,"abstract":"<div><div>Mediataxanes A–C (<strong>1</strong>–<strong>3</strong>), three unusual 4-oxo-20-<em>nor</em>-taxanes with 6/8/6 ring system were isolated from <em>Taxus × media</em> cell cultures. Their structures were determined by extensive spectroscopic data, and the absolute configurations were confirmed by X-ray crystallographic analysis (<strong>1</strong> and <strong>2</strong>) and NMR data comparison (<strong>3</strong>). Biological assay revealed that <strong>1</strong> exhibited moderate cytotoxicity against gastric carcinoma BGC823 and cervical cancer HeLa cells. In addition, a plausible mechanism for the oxidative cleavage of 4(20)-exocyclic-double bond and the formation of 4-carbonyl group in <strong>1</strong>–<strong>3</strong> is proposed.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155503"},"PeriodicalIF":1.5,"publicationDate":"2025-02-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143395967","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
Pd-catalyzed CH (phenylsulfonyl)difluoromethylation of electron-rich heteroarenes
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-05 DOI: 10.1016/j.tetlet.2025.155486
Zi-En Liu , Tao Lin , Yue Zhao, Jun Cao
{"title":"Pd-catalyzed CH (phenylsulfonyl)difluoromethylation of electron-rich heteroarenes","authors":"Zi-En Liu ,&nbsp;Tao Lin ,&nbsp;Yue Zhao,&nbsp;Jun Cao","doi":"10.1016/j.tetlet.2025.155486","DOIUrl":"10.1016/j.tetlet.2025.155486","url":null,"abstract":"<div><div>A novel Pd(0)-catalyzed C<img>H (phenylsulfonyl)difluoromethylation of electron-rich heteroarenes has been developed. The reaction utilizing PhSO<sub>2</sub>CF<sub>2</sub>I as a (phenylsulfonyl)difluoromethylation reagent proceeds efficiently. Mechanistic studies indicate that the C<img>H (phenylsulfonyl)difluoromethylation occurs <em>via</em> a radical pathway. This method demonstrates broad substrate compatibility, including a variety of heterocycles containing nitrogen, oxygen, and sulfur atoms, achieving excellent yields. This study provides an efficient and versatile approach for synthesizing (phenylsulfonyl)difluoromethylated heterocycles, which are valuable in pharmaceuticals, agrochemicals, and materials. The mild reaction conditions and high efficiency of this method make it a promising tool for expanding the scope of organofluorine chemistry applications.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155486"},"PeriodicalIF":1.5,"publicationDate":"2025-02-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143324810","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 conjugated dienes through dehydrgeogenative homocoupling reaction of vinyl CH substrates using oxygen as oxidant
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-05 DOI: 10.1016/j.tetlet.2025.155502
Xiaoke Luo , Yanmei Wen , Junjie Yang, Haisheng Xie
{"title":"Synthesis of conjugated dienes through dehydrgeogenative homocoupling reaction of vinyl CH substrates using oxygen as oxidant","authors":"Xiaoke Luo ,&nbsp;Yanmei Wen ,&nbsp;Junjie Yang,&nbsp;Haisheng Xie","doi":"10.1016/j.tetlet.2025.155502","DOIUrl":"10.1016/j.tetlet.2025.155502","url":null,"abstract":"<div><div>Palladium-catalyzed green oxidative homocoupling reactions of C<sub>vinyl</sub><img>H bonds of terminal alkenes produce conjugated dienes by using O<sub>2</sub> as the crucial oxidant. This method provides an efficient and environmentally compatible approach to 1,3-butadienes under mild conditions, addressing the need for more sustainable reaction processes. Our preliminary results demonstrate the viability of dehydrogenative C<sub>vinyl</sub><img>C<sub>vinyl</sub> bond-forming processes with molecular oxygen as the sole oxidant, offering a promising strategy for green chemistry applications.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155502"},"PeriodicalIF":1.5,"publicationDate":"2025-02-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143395966","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
Iron phthalocyanine-catalyzed aerobic oxidation of olefins enabled by metal-hydride hydrogen atom transfer
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-02-04 DOI: 10.1016/j.tetlet.2025.155492
Yunfei Liu, Kaikai Qiao, Junfeng Yang, Wenfeng Jiang, Rong Zhang, Lei Shi
{"title":"Iron phthalocyanine-catalyzed aerobic oxidation of olefins enabled by metal-hydride hydrogen atom transfer","authors":"Yunfei Liu,&nbsp;Kaikai Qiao,&nbsp;Junfeng Yang,&nbsp;Wenfeng Jiang,&nbsp;Rong Zhang,&nbsp;Lei Shi","doi":"10.1016/j.tetlet.2025.155492","DOIUrl":"10.1016/j.tetlet.2025.155492","url":null,"abstract":"<div><div>We have established an MHAT-driven oxidation process to transform olefins into ketones, using inexpensive and readily available iron phthalocyanine as a catalyst. Various acetophenone derivatives were obtained with a low catalyst loading of only 0.5 mol% at room temperature and in an air atmosphere. This methodology has good compatibility with a wide range of differently substituted functional groups.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155492"},"PeriodicalIF":1.5,"publicationDate":"2025-02-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143377443","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
Tin(II)-chloride (SnCl2) mediated reduction of α,β-alkynyl carbonyl compounds
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-31 DOI: 10.1016/j.tetlet.2025.155481
U. Ralepelle , E.N. Agbo , K. Lekgau , H. Chauke , I. Cukrowski , W. Nxumalo
{"title":"Tin(II)-chloride (SnCl2) mediated reduction of α,β-alkynyl carbonyl compounds","authors":"U. Ralepelle ,&nbsp;E.N. Agbo ,&nbsp;K. Lekgau ,&nbsp;H. Chauke ,&nbsp;I. Cukrowski ,&nbsp;W. Nxumalo","doi":"10.1016/j.tetlet.2025.155481","DOIUrl":"10.1016/j.tetlet.2025.155481","url":null,"abstract":"<div><div>An efficient Tin(II)-chloride (SnCl<sub>2</sub>) mediated reduction of α,β-alkynyl carbonyl compounds to their corresponding alkanes has been developed and reported. The developed method was optimized by varying parameters such as reaction time, temperature, and the equivalence of SnCl<sub>2</sub> using different solvents. The best reaction condition (80 % yield) involved 2.5 eq. of SnCl<sub>2</sub>, at 25 °C for 3 h in ethyl acetate. This method is applicable for the reduction of α,β-alkynyl carbonyl of quinoxaline, pyrimidine, pyrazine and pyridine.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"157 ","pages":"Article 155481"},"PeriodicalIF":1.5,"publicationDate":"2025-01-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143150500","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
An efficient and convenient reaction system based on MnAl layered double oxide for the aerobic oxidation of alkylarenes
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155426
Yihan Shan , Anwei Wang , Sifan Zhang , Deqin Liang , Mingyang He , Weiyou Zhou
{"title":"An efficient and convenient reaction system based on MnAl layered double oxide for the aerobic oxidation of alkylarenes","authors":"Yihan Shan ,&nbsp;Anwei Wang ,&nbsp;Sifan Zhang ,&nbsp;Deqin Liang ,&nbsp;Mingyang He ,&nbsp;Weiyou Zhou","doi":"10.1016/j.tetlet.2024.155426","DOIUrl":"10.1016/j.tetlet.2024.155426","url":null,"abstract":"<div><div>An efficient and convenient catalytic system has been reported for the aerobic oxidation of alkylarenes based on Mn<sub>2</sub>Al layered double oxide (Mn<sub>2</sub>Al-LDO) without any additives. The heterogeneous catalytic system could tolerate various alkylarenes with satisfactory yields. The results demonstrated that Mn species in Mn<sub>2</sub>Al-LDO are the catalytically active sites, and both HAT (hydrogen atom transfer) and ET/PT (electron transfer/proton transfer) processes were suggested to be ascribed for the transformation. A possible reaction mechanism has been proposed based on a series of control experiments.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155426"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159573","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
Dearomative electrophilic spirocyclization via the intramolecular Ritter reaction: Diastereoselective access to hydrogenated spiroindolenines
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155423
Yuliya S. Rozhkova, Arina S. Pegushina, Vyacheslav V. Morozov, Yurii V. Shklyaev
{"title":"Dearomative electrophilic spirocyclization via the intramolecular Ritter reaction: Diastereoselective access to hydrogenated spiroindolenines","authors":"Yuliya S. Rozhkova,&nbsp;Arina S. Pegushina,&nbsp;Vyacheslav V. Morozov,&nbsp;Yurii V. Shklyaev","doi":"10.1016/j.tetlet.2024.155423","DOIUrl":"10.1016/j.tetlet.2024.155423","url":null,"abstract":"<div><div>Dearomative electrophilic spirocyclization based on the intramolecular Ritter reaction of (2-methoxyphenyl)cyclohexan-1-ols with thiocyanates allows the diastereoselective access to the novel hydrogenated spiroindolenines containing a 2,4-cyclohexadienone moiety. The scope and limitations of the reaction were examined. Alkyl thiocyanates and benzyl thiocyanate afforded spiroindolenines in moderate to good yields, whereas the use of <em>β</em>-oxothiocyanates was ineffective. The efficiency of the reaction was also highly dependent on the substitution patterns of the starting alcohols, including substituents on the <em>α</em>-position to the hydroxy group and the 2-methoxyphenyl moiety.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155423"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159578","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
Spotting the unforeseen in the preparation of N-(azetidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine derivatives
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155427
Iva Brekalo , Zorica Marušić Ištuk , Milan Mesić , Marijo Čičak , Ivaylo J. Elenkov , Alberto Cuzzolin , Fabio Rancati , Alessandro Accetta
{"title":"Spotting the unforeseen in the preparation of N-(azetidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine derivatives","authors":"Iva Brekalo ,&nbsp;Zorica Marušić Ištuk ,&nbsp;Milan Mesić ,&nbsp;Marijo Čičak ,&nbsp;Ivaylo J. Elenkov ,&nbsp;Alberto Cuzzolin ,&nbsp;Fabio Rancati ,&nbsp;Alessandro Accetta","doi":"10.1016/j.tetlet.2024.155427","DOIUrl":"10.1016/j.tetlet.2024.155427","url":null,"abstract":"<div><div>Azetidine derivatives are a popular class of heterocycles in pharmacologically active molecules due to their rigidity, smaller size, and lower lipophilicity compared to pyrrolidines and piperidines, while maintaining similar basicity. However, azetidines exhibit unique reactivity dependent on stereoelectronic factors and reaction conditions, leading to potential instabilities and rearrangements during synthesis. In our attempt to prepare Abrocitinib analogues by replacing the <em>cis</em>-cyclobutane-1,3-diamine scaffold with azetidin-3-amine, we discovered an unforeseen rearrangement of the <em>N</em>-(azetidin-3-yl)-7<em>H</em>-pyrrolo[2,3-<em>d</em>]pyrimidin-4-amine substructure to the tricyclic (2,3-dihydro-1<em>H</em>-imidazo[1,2-<em>c</em>]pyrrolo[3,2-<em>e</em>]pyrimidin-2-yl)methanamine. These findings highlight the need for careful characterization of azetidine-containing compounds when based on <em>N</em>-(azetidin-3-yl)pyrimidin-4-amine substructures and suggest potential methods for preparation of new tricyclic scaffolds.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155427"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143160320","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 dihydrooxepinobenzofuranone derivatives via Claisen rearrangement and ring closing metathesis
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155447
Samyuktha Arimalai Dinakararaja , Ethiraj Kannatt Radhakrishnan
{"title":"Synthesis of dihydrooxepinobenzofuranone derivatives via Claisen rearrangement and ring closing metathesis","authors":"Samyuktha Arimalai Dinakararaja ,&nbsp;Ethiraj Kannatt Radhakrishnan","doi":"10.1016/j.tetlet.2024.155447","DOIUrl":"10.1016/j.tetlet.2024.155447","url":null,"abstract":"<div><div>A simple and effective protocol for synthesizing dihydrooxepinobenzofuranone derivatives was developed using Claisen Rearrangement (CR) and Ring Closing Metathesis (RCM). This protocol requires low catalyst loading and moderate heating to construct the 7-membered and 9-membered ring fused aurone derivatives in very short reaction times. Various substrates including biphenyl and hetero aryl aldehydes were well tolerated. The scope and limitations of the reactions were established. The structures of the representative compounds were established by Single Crystal X-ray Diffraction. Similarly, ene–yne RCM products were also synthesized by the same protocol.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155447"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159667","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
Reductive heck cyclization and functionalyzation of 5-bromohomoadamant-4-ene carboxamide derivatives: The route to homoadamantene annulated heterocycles
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-01-30 DOI: 10.1016/j.tetlet.2024.155431
Alexander N. Reznikov, Svetlana Yu. Vostruhina, Yury N. Klimochkin
{"title":"Reductive heck cyclization and functionalyzation of 5-bromohomoadamant-4-ene carboxamide derivatives: The route to homoadamantene annulated heterocycles","authors":"Alexander N. Reznikov,&nbsp;Svetlana Yu. Vostruhina,&nbsp;Yury N. Klimochkin","doi":"10.1016/j.tetlet.2024.155431","DOIUrl":"10.1016/j.tetlet.2024.155431","url":null,"abstract":"<div><div>Palladium catalyzed intramolecular reductive Heck reaction and Heck/cyanation domino sequence of 5-bromohomoadamant-4-ene carboxamides are a convenient synthetic pathway that provides access to polycyclic annulated homoadamanthene derivatives with 5,6-dihydropyridin-2(1<em>H</em>)-one and 1,5-dihydro-2<em>H</em>-pyrrol-2-one cores.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"155 ","pages":"Article 155431"},"PeriodicalIF":1.5,"publicationDate":"2025-01-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143159669","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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