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Total synthesis of the tetrasaccharide repeating units of Pseudomonas chlororaphis O-polysaccharide. 绿假单胞菌o型多糖四糖重复单元的全合成。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-08 DOI: 10.1039/d6ob01277a
Bhaswati Ghosh, Balasaheb K Ghotekar, Sourjya Mal, Suvarn S Kulkarni
{"title":"Total synthesis of the tetrasaccharide repeating units of <i>Pseudomonas chlororaphis O</i>-polysaccharide.","authors":"Bhaswati Ghosh, Balasaheb K Ghotekar, Sourjya Mal, Suvarn S Kulkarni","doi":"10.1039/d6ob01277a","DOIUrl":"https://doi.org/10.1039/d6ob01277a","url":null,"abstract":"<p><p>Herein we present the first total synthesis of the tetrasaccharide repeating units from <i>Pseudomonas chlororaphis</i> subsp. <i>aureofaciens</i> UCM B-111, achieved through a stepwise assembly of the core tetrasaccharide structure. The tetrasaccharide units consist of two D-glucosamine units at the terminals, with D-galactosamine and D-quinovosamine rare sugar unit linked by two α- and two β-glycosidic bonds. The total synthesis of 1 and 2 was accomplished <i>via</i> the longest linear sequences of 23 and 22 steps with an overall yield of 2.9% and 3.8%, respectively.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149134178","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
Photoinduced metal-free cascade silylation/cyclization of alkynes/alkynones with hydrosilanes to access 3-silylated benzothiophenes and thioflavones. 光诱导无金属级联硅基化/环化炔/炔酮与氢硅烷得到3-硅基化苯并噻吩和硫黄酮。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-08 DOI: 10.1039/d6ob01346e
Yunfei Tian, Weijun Fu, Zhiqiang Wang, Xi Li, Jinzhao Ren, Yukai Liu, Luping Zheng, Kai Sun, Zejiang Li
{"title":"Photoinduced metal-free cascade silylation/cyclization of alkynes/alkynones with hydrosilanes to access 3-silylated benzothiophenes and thioflavones.","authors":"Yunfei Tian, Weijun Fu, Zhiqiang Wang, Xi Li, Jinzhao Ren, Yukai Liu, Luping Zheng, Kai Sun, Zejiang Li","doi":"10.1039/d6ob01346e","DOIUrl":"https://doi.org/10.1039/d6ob01346e","url":null,"abstract":"<p><p>A metal-free photocatalytic method for the synthesis of silylated thioflavones and benzothiophenes has been established through cascade silylation/cyclization of alkynes/alkynones with hydrosilanes. This transformation features mild reaction conditions, excellent functional group compatibility, and broad substrate scope. Moreover, this method can be readily applied to the late-stage silylation of structurally complex bioactive molecules, thus offering potential applications for pharmaceutical research. Mechanistic investigations indicate that this reaction proceeds through a radical pathway.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149126106","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
The first thermal epimerization of 2-piperidinones and tetrahydropyridines in DMSO: synthesis, DFT calculations and NCI analysis. 2-哌啶酮和四氢吡啶在DMSO中的首次热外映：合成、DFT计算和NCI分析。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-08 DOI: 10.1039/d6ob00476h
Andrey D Vinokurov, Taygib M Iliyasov, Kirill A Karpenko, Nikolai V Krivoshchapov, Fedor M Ravcheev, Alexander S Goloveshkin, Michail N Elinson, Anatoly N Vereshchagin
{"title":"The first thermal epimerization of 2-piperidinones and tetrahydropyridines in DMSO: synthesis, DFT calculations and NCI analysis.","authors":"Andrey D Vinokurov, Taygib M Iliyasov, Kirill A Karpenko, Nikolai V Krivoshchapov, Fedor M Ravcheev, Alexander S Goloveshkin, Michail N Elinson, Anatoly N Vereshchagin","doi":"10.1039/d6ob00476h","DOIUrl":"https://doi.org/10.1039/d6ob00476h","url":null,"abstract":"<p><p>Research into the epimerization of piperidine-2-ones is exceedingly scarce. Blue light can induce epimerization of piperidine-2-ones, but this transformation necessitates the use of a blue LED and an iridium photocatalyst. We describe here the epimerization reactions of 2-piperidone-substituted pyridinium salts and 1,4,5,6-tetrahydropyridines in DMSO. The method is easy to perform and requires no catalysts or additional bases. An epimerization mechanism was proposed for each of these cases, and density functional theory (DFT) calculations were performed. With the aid of the noncovalent interaction (NCI) index, we were able to identify weak interactions within the molecule of a thermodynamically favorable epimer and compare them with those of a less thermodynamically favorable one.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.8,"publicationDate":"2026-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149126096","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
Brønsted acid-catalyzed (3 + 2) cycloaddition of 2-indolylmethanols with o-alkynylnaphthols toward the construction of cyclopenta[b]indoles. Brønsted酸催化2-吲哚甲醇与邻炔基萘酚（3 + 2）环加成合成环五[b]吲哚。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-07 DOI: 10.1039/d6ob01208f
Wen-Tao Zhang, Xi Zhou, Fa-Fu Zhou, Hong-Yi Zhu, Wei Tan, Feng Shi
{"title":"Brønsted acid-catalyzed (3 + 2) cycloaddition of 2-indolylmethanols with <i>o</i>-alkynylnaphthols toward the construction of cyclopenta[<i>b</i>]indoles.","authors":"Wen-Tao Zhang, Xi Zhou, Fa-Fu Zhou, Hong-Yi Zhu, Wei Tan, Feng Shi","doi":"10.1039/d6ob01208f","DOIUrl":"https://doi.org/10.1039/d6ob01208f","url":null,"abstract":"<p><p>A Brønsted acid-catalyzed (3 + 2) cycloaddition of 2-indolylmethanols with <i>o</i>-alkynylnaphthols has been developed, leading to the efficient synthesis of cyclopenta[<i>b</i>]indoles with structural diversity in generally high yields. This study presents the first application of alkynes as 2C reaction partners in cycloadditions of 2-indolylmethanols. Furthermore, a chiral resolution strategy was developed using (<i>R</i>)-(-)-<i>O</i>-formylmandeloyl chloride as a resolution reagent to obtain optically pure cyclopenta[<i>b</i>]indole atropisomers from racemic substrates. Additionally, a catalytic asymmetric version of this (3 + 2) cycloaddition has been preliminarily explored, which disclosed the potential of the reaction for the enantioselective synthesis of axially chiral cyclopenta[<i>b</i>]indoles. This work not only offers a practical approach for the synthesis of cyclopenta[<i>b</i>]indoles bearing indole-fused five-membered rings but also expands the scope of indolylmethanol chemistry.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"24 38","pages":"8009-8016"},"PeriodicalIF":2.8,"publicationDate":"2026-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149126144","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
Photocatalytic synthesis of sulfonamidylated chroman-4-ones: metal- and oxidant-free radical addition-cyclization. 磺酰胺化铬-4-酮的光催化合成：金属自由基和氧化剂自由基加成-环化。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-07 DOI: 10.1039/d6ob01143h
Qiwei Qiao, Hong Sun, Pirada Sudprasert, Jin Cheng
{"title":"Photocatalytic synthesis of sulfonamidylated chroman-4-ones: metal- and oxidant-free radical addition-cyclization.","authors":"Qiwei Qiao, Hong Sun, Pirada Sudprasert, Jin Cheng","doi":"10.1039/d6ob01143h","DOIUrl":"https://doi.org/10.1039/d6ob01143h","url":null,"abstract":"<p><p>A metal- and oxidant-free photocatalytic cascade reaction has been developed for the divergent synthesis of sulfonamidylated chroman-4-ones. This visible-light-driven protocol employs readily available <i>o</i>-(allyloxy)arylaldehydes and <i>N</i>-sulfonylaminopyridinium salts as feedstocks. A sulfonamidyl radical-triggered addition-cyclization sequence enables the one-step assembly of a new heterocyclic ring with the concomitant formation of C-N and C-C bonds. The mild conditions afford the desired products in moderate to good yields, obviating the need for noble-metal catalysts or external oxidants. This sustainable strategy not only enriches the structural diversity of chroman-4-one scaffolds but also paves the way for constructing bioactive compound libraries.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":"24 38","pages":"7908-7913"},"PeriodicalIF":2.8,"publicationDate":"2026-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149126167","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
One-pot construction of pyrazolo[5,1-a]isoindoles via t-butyl carbazate-mediated double Michael addition/cyclocondensation of diaroyl benzothiepine-1,1-dioxides. 邻苯并噻吩-1,1-二氧化物双Michael加成/环缩合一锅法合成吡唑[5,1-a]异吲哚。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-07 DOI: 10.1039/d6ob01229a
Meng-Yang Chang, Yu-Hsuan Liu
{"title":"One-pot construction of pyrazolo[5,1-<i>a</i>]isoindoles <i>via t</i>-butyl carbazate-mediated double Michael addition/cyclocondensation of diaroyl benzothiepine-1,1-dioxides.","authors":"Meng-Yang Chang, Yu-Hsuan Liu","doi":"10.1039/d6ob01229a","DOIUrl":"10.1039/d6ob01229a","url":null,"abstract":"<p><p>This article reports one-pot synthesis of aroylmethyl-conjugated pyrazolo[5,1-<i>a</i>]isoindoles <i>via t</i>-butyl carbazate-mediated double Michael addition/cyclocondensation of diaroyl benzothiepine-1,1-dioxides. In the reaction process, the seven-membered ring is converted into a bicyclo[5.5] core skeleton by the formation of two carbon-nitrogen single bonds and one carbon-nitrogen double bond under mild conditions. The related plausible mechanism is also discussed here.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"7933-7939"},"PeriodicalIF":2.8,"publicationDate":"2026-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149011682","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
Copper(II)-catalyzed C3-acylation of quinoxalin-2(1H)-ones with methyl ketones via the formal decarbonylation of 1,2-diketones. 铜（II）催化喹啉-2(1H)- 1通过1,2-二酮的形式脱羰化与甲基酮的c3酰化。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-07 DOI: 10.1039/d6ob01048b
Raju Lal Dhakar, Pundalik Baliram Polawad, Hritik Prakash Kaushal, Patel Kevin Bhanubhai, S Banuprakash Goud, Sampak Samanta
{"title":"Copper(II)-catalyzed C3-acylation of quinoxalin-2(1<i>H</i>)-ones with methyl ketones <i>via</i> the formal decarbonylation of 1,2-diketones.","authors":"Raju Lal Dhakar, Pundalik Baliram Polawad, Hritik Prakash Kaushal, Patel Kevin Bhanubhai, S Banuprakash Goud, Sampak Samanta","doi":"10.1039/d6ob01048b","DOIUrl":"10.1039/d6ob01048b","url":null,"abstract":"<p><p>The inexpensive copper(II) bromide-catalyzed cross-dehydrogenative coupling/Kornblum oxidation/formal decarbonylation of <i>N</i>-substituted/unsubstituted quinoxalinones in DMSO is reported. It has offered a new technique for the cleavage of C(CO)-C(CO) bonds under base- and ligand-free conditions, allowing for the direct synthesis of a diverse range of C3-acylated quinoxalinones. This persulfate-peroxide-free catalytic method provides good yields, a broad substrate scope, and good tolerance to various functionalities.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"7925-7932"},"PeriodicalIF":2.8,"publicationDate":"2026-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149011685","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
Spatiotemporally controlled degradation of CDK6 via light-triggered ROS generation: uncovering the proximity effect-mediated dual target depletion. 通过光触发ROS产生的CDK6的时空控制降解：揭示邻近效应介导的双靶标损耗。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-07 DOI: 10.1039/d6ob00828c
Wei Zhang, Longli Hu, Yan He, Yu Zhang, Huan He, Silong Zhang
{"title":"Spatiotemporally controlled degradation of CDK6 <i>via</i> light-triggered ROS generation: uncovering the proximity effect-mediated dual target depletion.","authors":"Wei Zhang, Longli Hu, Yan He, Yu Zhang, Huan He, Silong Zhang","doi":"10.1039/d6ob00828c","DOIUrl":"10.1039/d6ob00828c","url":null,"abstract":"<p><p>Cyclin-dependent kinase 6 (CDK6) is a key therapeutic target in breast cancer, and its abnormal activation, together with Cyclin D3, promotes uncontrolled cell proliferation. Traditional CDK4/6 inhibitors only inhibit kinase activity without degrading the target protein, which readily causes drug resistance. In this study, we designed and synthesized a series of photo-controlled CDK6 degraders (LL1-LL7) using palbociclib as the core pharmacophore and linking photosensitizers to generate reactive oxygen species (ROS) under light. Among them, LL5 showed the best CDK6 degradation and antiproliferative activity. LL5 produces ROS <i>via</i> a Type II mechanism under 450 ± 25 nm LED light and elevates intracellular ROS in T47D cells. Western blot revealed that LL5 barely affected CDK6 and Cyclin D3 in the dark but markedly degraded both proteins after 15 min of irradiation, owing to ROS-mediated structural damage and the proximity effect between the two proteins. Functional assays showed that light irradiation significantly enhanced the antiproliferative activity of LL5. It displayed good selectivity between cancer and normal breast epithelial cells and induced G0/G1 arrest and apoptosis in T47D cells under light. In conclusion, LL5 acts as a photo-controlled degrader that co-degrades CDK6 and Cyclin D3 through light-triggered ROS and proximity effects, offering a promising new strategy for breast cancer treatment.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"7957-7969"},"PeriodicalIF":2.8,"publicationDate":"2026-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149014883","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
Metal-free N-acylation of sulfoximines with carboxylic acids via N-chlorophthalimide/triphenylphosphine-mediated activation. 通过n -氯酞酰亚胺/三苯基膦介导活化的亚砜亚胺与羧酸的无金属n -酰化。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-07 DOI: 10.1039/d6ob01123c
Kishor R Thete, V Kumar, Devidas A More, M Muthukrishnan
{"title":"Metal-free <i>N</i>-acylation of sulfoximines with carboxylic acids <i>via N</i>-chlorophthalimide/triphenylphosphine-mediated activation.","authors":"Kishor R Thete, V Kumar, Devidas A More, M Muthukrishnan","doi":"10.1039/d6ob01123c","DOIUrl":"10.1039/d6ob01123c","url":null,"abstract":"<p><p>Herein, we describe a metal-free <i>N</i>-acylation of sulfoximines mediated by an <i>N</i>-chlorophthalimide/triphenylphosphine (NCP/PPh<sub>3</sub>) system. The transformation proceeds under mild reaction conditions and provides efficient access to structurally diverse <i>N</i>-acyl sulfoximines in good yields. The protocol exhibits a broad substrate scope, excellent functional-group tolerance, and is readily scalable. Notably, the protocol applies to aromatic, benzylic, and α-keto carboxylic acids, providing straightforward access to a wide range of <i>N</i>-acyl sulfoximines of potential biological relevance.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"7892-7897"},"PeriodicalIF":2.8,"publicationDate":"2026-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148987196","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
Total synthesis of kasichelins A and B. 卡西林蛋白A和B的全合成。
IF 2.8 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2026-10-07 DOI: 10.1039/d6ob01259k
Yu-Qin Tang, Xue-Hua Huang, Xin-Yi Tong, Ye Liang, Jia-Lei Yan, Ai-Jun Ma
{"title":"Total synthesis of kasichelins A and B.","authors":"Yu-Qin Tang, Xue-Hua Huang, Xin-Yi Tong, Ye Liang, Jia-Lei Yan, Ai-Jun Ma","doi":"10.1039/d6ob01259k","DOIUrl":"10.1039/d6ob01259k","url":null,"abstract":"<p><p>The first total synthesis of kasichelins A and B was accomplished in a concise manner <i>via</i> a longest linear sequence of seven steps with 25% and 18% overall yields, respectively. The synthetic route featured a judicious choice of protecting groups, a molybdenum-promoted dehydrative cyclization for construction of the dihydrooxazole core, and a convergent fragment assembly strategy to forge the complete molecular scaffold.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":"7914-7917"},"PeriodicalIF":2.8,"publicationDate":"2026-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"148987210","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
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