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Redox-neutral-photocatalyzed decarboxylative radical addition/acyl migration cascade process: modular access to functionalized α-(hetero)aryl-α-aminoketones.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-09 DOI: 10.1039/d5ob00290g
Haibo Huang, Yu Zhao, Li Zhang, Yan Li, Yewen Fang
{"title":"Redox-neutral-photocatalyzed decarboxylative radical addition/acyl migration cascade process: modular access to functionalized α-(hetero)aryl-α-aminoketones.","authors":"Haibo Huang, Yu Zhao, Li Zhang, Yan Li, Yewen Fang","doi":"10.1039/d5ob00290g","DOIUrl":"https://doi.org/10.1039/d5ob00290g","url":null,"abstract":"<p><p>Herein, using reductive radical-polar crossover as a key process, a robust and practical protocol for the N → C acyl migration reaction has been successfully developed. A variety of enamides could react with carboxylic acids for modular access to α-(hetero)aryl-α-aminoketones enabled by redox-neutral photocatalysis. This decarboxylative radical addition/acyl migration cascade process features a broad substrate scope, good functional compatibility, and mild reaction conditions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143810385","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
Semisynthesis of bersavine and berbamine derivatives that target the CaMKIIγ:cMyc axis for lymphoma therapy.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-09 DOI: 10.1039/d5ob00310e
Berkley Lujan, Mingfeng Zhang, Yujie Cao, Arnav Kacker, Lina Mai, Shunquan Wu, Taylor Alexander, Wendong Huang, Kevin G M Kou
{"title":"Semisynthesis of bersavine and berbamine derivatives that target the CaMKIIγ:cMyc axis for lymphoma therapy.","authors":"Berkley Lujan, Mingfeng Zhang, Yujie Cao, Arnav Kacker, Lina Mai, Shunquan Wu, Taylor Alexander, Wendong Huang, Kevin G M Kou","doi":"10.1039/d5ob00310e","DOIUrl":"https://doi.org/10.1039/d5ob00310e","url":null,"abstract":"<p><p>Berbamine, a bisbenzylisoquinoline alkaloid (bisBIA), is a promising lead for developing novel therapeutics to treat aggressive cancers such as lymphoma, by targeting the CaMKIIγ:cMyc axis. Herein, we report an aza-Friedel-Crafts method for <i>ortho</i>-aminoalkylation of berbamine's phenolic motif, enabling the semisynthesis of the natural product bersavine and analogs that complement current methods focusing on modifying the phenolic oxygen. Several new analogs synthesized by this method exhibit potent cytotoxicity against lymphoma-associated cell line H9 exceeding the naturally occurring berbamine (1) and bersavine (3a). A molecular docking analysis was used to devise a model that rationalizes the structure-activity relationship between the novel bisBIA analogs and CaMKIIγ inhibition.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143810388","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
Kinetic resolution of binols and biphenols via dehydrogenative coupling with hydrosilanes catalyzed by chiral FLPs.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-09 DOI: 10.1039/d5ob00347d
Zijia Zhang, Xiangqing Feng, Haifeng Du
{"title":"Kinetic resolution of binols and biphenols <i>via</i> dehydrogenative coupling with hydrosilanes catalyzed by chiral FLPs.","authors":"Zijia Zhang, Xiangqing Feng, Haifeng Du","doi":"10.1039/d5ob00347d","DOIUrl":"https://doi.org/10.1039/d5ob00347d","url":null,"abstract":"<p><p>A kinetic resolution of binols and biphenols has been realized <i>via</i> dehydrogenative coupling with hydrosilanes catalyzed by a frustrated Lewis pair of chiral borane and chiral phosphine. A variety of axially chiral siloxanes, along with the corresponding optically active binols and biphenols, were obtained in good yields with moderate to high enantioselectivities.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143810383","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
A versatile approach toward enantiospecific synthesis of sugar-linked oxapolyquinanes via IPKR.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-09 DOI: 10.1039/d4ob02016b
Kanchan Maurya, Krishna P Kaliappan
{"title":"A versatile approach toward enantiospecific synthesis of sugar-linked oxapolyquinanes <i>via</i> IPKR.","authors":"Kanchan Maurya, Krishna P Kaliappan","doi":"10.1039/d4ob02016b","DOIUrl":"https://doi.org/10.1039/d4ob02016b","url":null,"abstract":"<p><p>An efficient and enantiospecific synthetic strategy for the construction of [6/5/5/5] and [5/5/5/5] fused oxatetraquinanes using a D-glucose-derived enyne has been described. The approach integrates oxidative cleavage, organoaluminium-mediated propargylation, and IPKR (Intramolecular Pauson-Khand Reaction) to deliver the tetracyclic core with high stereoselectivity. These tetracyclic cores serve as versatile synthons for the synthesis of more complex [6/5/5/5/5] fused polyquinanes. This methodology not only highlights the strategic use of carbohydrate-derived enynes but also provides a robust platform for the asymmetric synthesis of structurally intricate polyquinanes, paving the way for the development of biologically relevant molecular frameworks.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143810339","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
Dual palladium-organophotoredox catalyzed C-H olefination-annulation of aryl carboxylic acids.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-09 DOI: 10.1039/d5ob00275c
A Anagha Varma, Purushothaman Gopinath
{"title":"Dual palladium-organophotoredox catalyzed C-H olefination-annulation of aryl carboxylic acids.","authors":"A Anagha Varma, Purushothaman Gopinath","doi":"10.1039/d5ob00275c","DOIUrl":"https://doi.org/10.1039/d5ob00275c","url":null,"abstract":"<p><p>Herein, we report a dual palladium-photoredox mediated tandem C-H olefination-cyclization of aryl carboxylic acids with both terminal and internal alkenes using molecular oxygen as a green oxidant. This method offers a mild and simple route for the synthesis of various isobenzofuranone derivatives. The synthetic utility of the method was demonstrated by late stage functionalization of various carboxylic acid containing drugs. Further derivatizations of the final isobenzofuranones were performed to access other important molecular scaffolds. Mechanistic studies indicated that the final cyclization step involves an oxopalladation-protodemetallation mechanism rather than a simple oxa-Michael addition commonly employed in other methodologies at elevated temperatures.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143810381","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
Photoswitchable agonists for visible-light activation of the Wnt signaling pathway.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-08 DOI: 10.1039/d4ob01827c
Shifa Ahmad, P K Hashim, Masamichi Imajo, Nusaiba Madappuram Cheruthu, Kiyonori Takahashi, Shinya Tanaka, Takayoshi Nakamura, Nobuyuki Tamaoki
{"title":"Photoswitchable agonists for visible-light activation of the Wnt signaling pathway.","authors":"Shifa Ahmad, P K Hashim, Masamichi Imajo, Nusaiba Madappuram Cheruthu, Kiyonori Takahashi, Shinya Tanaka, Takayoshi Nakamura, Nobuyuki Tamaoki","doi":"10.1039/d4ob01827c","DOIUrl":"https://doi.org/10.1039/d4ob01827c","url":null,"abstract":"<p><p>Based on the known Wnt agonist BML-284, we designed and synthesized photoswitchable azo derivative compounds that can act as agonists for the Wnt signaling pathway. These photoswitchable agonists were shown to undergo reversible <i>trans</i>-<i>cis</i> isomerization upon being irradiated with visible light, but only the <i>cis</i> isomer was observed to activate the Wnt signaling pathway, using a luminescense-based reporter assay in cultured cells. One of the compounds, denoted as compound 2, showed ∼88% agonist activity after being subjected to visible light irradiation in comparison to the non-photoswitchable BML-284. We also were able to selectively activate the Wnt signaling pathway using 2 and light irradiation at a specific region of interest in a model cell culture system, highlighting the ability to achieve spatiotemporal regulation.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143801956","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
Enantioselective construction of functionalized oxazoles via anionic stereogenic-at-cobalt(III) complex-catalyzed Ugi-4CR/Wittig reaction sequences.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-08 DOI: 10.1039/d5ob00293a
Qi-Ming Wang, Chang-Min Peng, Yong-En Sun, Chuan-Zhi Yao, Hua-Jie Jiang, Jie Yu
{"title":"Enantioselective construction of functionalized oxazoles <i>via</i> anionic stereogenic-at-cobalt(III) complex-catalyzed Ugi-4CR/Wittig reaction sequences.","authors":"Qi-Ming Wang, Chang-Min Peng, Yong-En Sun, Chuan-Zhi Yao, Hua-Jie Jiang, Jie Yu","doi":"10.1039/d5ob00293a","DOIUrl":"https://doi.org/10.1039/d5ob00293a","url":null,"abstract":"<p><p>A one-pot synthesis of chiral multifunctional oxazole frameworks is accomplished <i>via</i> a cascade reaction involving an anionic stereogenic cobalt(III) complex-catalyzed enantioselective Ugi four-component/Wittig process. This approach tolerates a complex reaction system that includes aldehydes, amines, carboxylic acids, and isocyano-(triphenylphosphoranylidene)acetates, yielding chiral 2,4,5-trisubstituted oxazoles with good enantioselectivities (up to 93 : 7 er).</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143801948","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
Iron-catalyzed peroxidation of fluorenes and 9-alkyl-9H-fluorenes and oxidative cleavage of the CC bond in 9-alkylidene-fluorenes.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-08 DOI: 10.1039/d5ob00102a
Ratnakar Saha, Bhairab Chand Hembram, Asutosh Panda, Bidraha Bagh
{"title":"Iron-catalyzed peroxidation of fluorenes and 9-alkyl-9<i>H</i>-fluorenes and oxidative cleavage of the CC bond in 9-alkylidene-fluorenes.","authors":"Ratnakar Saha, Bhairab Chand Hembram, Asutosh Panda, Bidraha Bagh","doi":"10.1039/d5ob00102a","DOIUrl":"https://doi.org/10.1039/d5ob00102a","url":null,"abstract":"<p><p>A newly developed (NNN)FeCl<sub>2</sub> complex was used as an efficient catalyst for the quaternary peroxidation of 9-alkyl-9<i>H</i>-fluorenes <i>via</i> selective C-H functionalization. This peroxidation involved a radical pathway. Peroxidation of 9<i>H</i>-fluorenes was also performed efficiently. The iron catalyst is also effective for the oxidative cleavage of the CC bond in 9-alkylidene fluorenes to yield 9-fluorenones.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143801953","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
Ionic liquids in C-H activation: synthesis and functionalization of heterocycles and carbocycles.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-08 DOI: 10.1039/d4ob02109f
Kamal Kant, Priyadarshini Naik, Jyoti, Nayyef Aljaar, Chandi C Malakar
{"title":"Ionic liquids in C-H activation: synthesis and functionalization of heterocycles and carbocycles.","authors":"Kamal Kant, Priyadarshini Naik, Jyoti, Nayyef Aljaar, Chandi C Malakar","doi":"10.1039/d4ob02109f","DOIUrl":"https://doi.org/10.1039/d4ob02109f","url":null,"abstract":"<p><p>This review illustrates various roles played by ionic liquids in organic transformations, such as solvents, additives, promoters, electrolytes and catalysts for the synthesis and functionalization of heterocycles and carbocycles through C-H activation reactions. Ionic liquids offer several advantages such as high stability, intrinsic conductivity, non-volatility, and recyclability, making them appealing alternatives to traditional organic solvents in sustainable organic synthesis. Their unique properties enhance reaction performance, as seen with recyclable [EMIM]BF<sub>4</sub> in quinazolinone synthesis and [TMG][CF<sub>3</sub>COO] in amide production, direct diarylation of 6,7-benzindoles, regioselective reactions with aryl iodides, catalytic cyclopropanation with tetrabutylammonium acetate (TBAA), and propargylamine synthesis <i>via</i> A<sup>3</sup> coupling reactions. The use of functionalized ionic liquids like [Bmim]PF<sub>6</sub> with phosphine-ligated Pd(II) enhances product isolation, facilitates reactions under mild conditions, and promotes reusability, contributing to environmentally friendly pathways. Thus, this review highlights various ionic liquids used in different reactions, emphasizing their benefits in improving yields, solubility, and product separation in catalytic processes.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143801951","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
EosinY and copper-catalyzed oxidative [2 + 3] annulation of glycine esters with oxiranes and thiiranes under light free conditions.
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-04-08 DOI: 10.1039/d5ob00148j
Raghunath Chowdhury
{"title":"EosinY and copper-catalyzed oxidative [2 + 3] annulation of glycine esters with oxiranes and thiiranes under light free conditions.","authors":"Raghunath Chowdhury","doi":"10.1039/d5ob00148j","DOIUrl":"https://doi.org/10.1039/d5ob00148j","url":null,"abstract":"<p><p>Herein, we report an oxidative formal [2 + 3] cycloaddition reaction of glycine esters with oxiranes/thiiranes under non-photoredox conditions using the catalytic system consisting of eosin-Y, Cu(OAc)<sub>2</sub> and HI. This one-pot protocol delivers an array of oxazolidine-2-carboxylic acids and thiaoxazolidine-2-carboxylic acid derivatives in moderate to good yields under mild reaction conditions. The value of this methodology is demonstrated in preparative scale reactions and downstream synthetic transformations. Based on a series of control experiments, a mechanistic pathway is also proposed.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143801949","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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