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Organic chemistry frontiers : an international journal of organic chemistry最新文献

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Phosphoric acid activation, reduction and transformation processes: efficient preparation of triarylphosphines† 磷酸活化、还原和转化工艺：高效制备三芳基膦
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-28 DOI: 10.1039/d5qo00278h
Yaling Tian , Tao Liu , Yao Chai , Zhibin Wang , Zhengyin Du , Xi-Cun Wang , Xiaofeng Wu , Zheng-Jun Quan
{"title":"Phosphoric acid activation, reduction and transformation processes: efficient preparation of triarylphosphines†","authors":"Yaling Tian ,&nbsp;Tao Liu ,&nbsp;Yao Chai ,&nbsp;Zhibin Wang ,&nbsp;Zhengyin Du ,&nbsp;Xi-Cun Wang ,&nbsp;Xiaofeng Wu ,&nbsp;Zheng-Jun Quan","doi":"10.1039/d5qo00278h","DOIUrl":"10.1039/d5qo00278h","url":null,"abstract":"<div><div>In this study, we developed a pre-activation reduction strategy to enable the efficient activation, reduction, and conversion of inert phosphate. Our method allows for the direct activation of [TBA][H<sub>2</sub>PO<sub>4</sub>] using oxalyl chloride at room temperature, followed by reduction with HSiCl<sub>3</sub>, enabling rapid synthesis of the low-valent bis(trichlorosilyl)phosphorylated anion [P(SiCl<sub>3</sub>)<sub>2</sub>]<sup>−</sup> in 24 h. Follow-up experiments demonstrated that the resulting anion could be successfully coupled with aryl halides by Pd-catalyst leading to the synthesis of a series of triarylphosphine compounds with good tolerance to a wide range of functionalized aryl halides. This represents a novel strategy for synthesizing organophosphorus compounds (OPCs) from phosphoric acid.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 13","pages":"Pages 3799-3806"},"PeriodicalIF":0.0,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143654068","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Deconstructive dicarbofunctionalization of cyclic amines enabled by C–H and C–N bond activation† C-H和C-N键激活环胺的解构双碳功能化
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-28 DOI: 10.1039/d5qo00270b
Qiming Zhu , Kaifang Wang , Yuyuan Fan , Tianze Zhang , Xianchen Song , Shuang Luo , Qiang Zhu , Hanmin Huang
{"title":"Deconstructive dicarbofunctionalization of cyclic amines enabled by C–H and C–N bond activation†","authors":"Qiming Zhu ,&nbsp;Kaifang Wang ,&nbsp;Yuyuan Fan ,&nbsp;Tianze Zhang ,&nbsp;Xianchen Song ,&nbsp;Shuang Luo ,&nbsp;Qiang Zhu ,&nbsp;Hanmin Huang","doi":"10.1039/d5qo00270b","DOIUrl":"10.1039/d5qo00270b","url":null,"abstract":"<div><div>The incorporation of nitrogen-containing heterocycles by the deconstruction of cycloamines with nucleophiles represents a powerful method in organic synthesis. However, this paradigm faces severe challenges in the simultaneous construction of C–N and C–C bonds that are typically encountered in pharmaceuticals. Herein, a metal- and catalyst-free C–N and C–H bond activation reaction mediated by a haloarene-derived aryne intermediate is identified that enables the deconstructive dicarbofunctionalization of cyclic amines. With this facile method, a variety of amines can undergo direct dicarbo-functionalization reactions with highly accessible aryl halides and hydrocarbons, yielding <em>N</em>-arylpiperazines and functionalized arylamines with great potential as drug candidates.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 13","pages":"Pages 3819-3825"},"PeriodicalIF":0.0,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143666407","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Stable sulfonate esters as C1-synthons for cyclopropanation reaction to access antimicrobial active 3,3′-spirocyclopropyloxindoles† 稳定的磺酸酯作为环丙化反应的c1合成物以获得具有抗菌活性的3,3 ' -螺环丙基氧吲哚
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-28 DOI: 10.1039/d5qo00153f
Yijie Long , Pinpin Feng , Hongyan Long , Yi Huang , Xingxing Wu
{"title":"Stable sulfonate esters as C1-synthons for cyclopropanation reaction to access antimicrobial active 3,3′-spirocyclopropyloxindoles†","authors":"Yijie Long ,&nbsp;Pinpin Feng ,&nbsp;Hongyan Long ,&nbsp;Yi Huang ,&nbsp;Xingxing Wu","doi":"10.1039/d5qo00153f","DOIUrl":"10.1039/d5qo00153f","url":null,"abstract":"<div><div>Alkyl sulfonyl chlorides widely serve as sulfene precursors to facilitate diverse transformations but suffer from poor hydrolytic stability under basic conditions, posing notable operational challenges. Consequently, the development of stable, easy-to-handle alternatives has garnered considerable interest for broad synthetic applications. Herein, we describe the efficient synthesis of spirocyclopropyloxindoles through a NaH-mediated formal [2 + 1] annulation using stable while reactive 4-nitrophenyl sulfonates as C1 synthons. Unexpectedly, the reaction proceeds through an unconventional [(2 + 2) − 1] pathway under basic conditions when using sulfonates and alkylidene oxindole substrates, deviating from conventional reaction modes. This approach affords spirocyclopropyloxindoles with high yields and good diastereoselectivity. Furthermore, these scaffolds demonstrate promising antibacterial activity against plant pathogens, highlighting their potential as novel agrochemical agents.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 13","pages":"Pages 3863-3869"},"PeriodicalIF":0.0,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143654069","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Direct Suzuki–Miyaura cross-coupling of C(sp2)–B(dan) bonds: designed in pursuit of usability† 为追求可用性而设计的C(sp2) -B （dan）键的直接Suzuki-Miyaura交叉耦合
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-28 DOI: 10.1039/d5qo00230c
Hiroki Andoh , Ryo Nakagawa , Tatsuya Akutagawa , Eiko Katata , Teruhisa Tsuchimoto
{"title":"Direct Suzuki–Miyaura cross-coupling of C(sp2)–B(dan) bonds: designed in pursuit of usability†","authors":"Hiroki Andoh ,&nbsp;Ryo Nakagawa ,&nbsp;Tatsuya Akutagawa ,&nbsp;Eiko Katata ,&nbsp;Teruhisa Tsuchimoto","doi":"10.1039/d5qo00230c","DOIUrl":"10.1039/d5qo00230c","url":null,"abstract":"<div><div>We developed practical reaction conditions and a procedure for the direct Suzuki–Miyaura cross-coupling (SMCC) of C(sp<sup>2</sup>)–B(dan) bonds. Below are important notes to successfully execute the direct SMCC: (1) dehydrated conditions that exclude as much H<sub>2</sub>O as possible are required, (2) LiOH is the base of choice, (3) dppf is the ligand of choice when using electron-deficient (hetero)aryl halides [(Het)ArX], (4) P(<em>t</em>-Bu)<sub>3</sub> is the ligand of choice when using electron-rich (Het)ArX, and (5) COD is the ligand of choice when using (Het)ArX with a protic functional group such as NH<sub>2</sub> and OH. Taking heed of these notes enables the direct SMCC of the C(sp<sup>2</sup>)–B(dan) bond by using a wide range of substrates with diverse functional groups, affording the following series of coupling products: Ar–Ar, Ar–HetAr, HetAr–HetAr, alkenyl–Ar, and alkenyl–alkenyl. Sequentially executing distinct types of palladium-catalyzed CCs, such as Buchwald–Hartwig CC + SMCC, Mizoroki–Heck reaction + SMCC, and Sonogashira–Hagihara CC + SMCC, allows access to complex π-conjugated molecules. The B(dan) moiety also exhibits outstanding compatibility with Wittig olefination and Sc(OTf)<sub>3</sub>-catalyzed acetal-forming reactions, enabling molecular transformations that are otherwise impracticable when using ArB(OH)<sub>2</sub>. Mechanistic studies suggest the involvement of both path A, wherein a boronate species reacts with an arylpalladium halide, and path B, wherein a boron compound reacts with an arylpalladium hydroxide, at the stage of the transmetalation.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 13","pages":"Pages 3759-3774"},"PeriodicalIF":0.0,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143813749","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
EDA complex photochemistry as a strategy for C–S bond formation EDA复合光化学作为C-S键形成的策略
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-28 DOI: 10.1039/d5qo00258c
Helena F. Piedra , Illán Tagarro , Manuel Plaza
{"title":"EDA complex photochemistry as a strategy for C–S bond formation","authors":"Helena F. Piedra ,&nbsp;Illán Tagarro ,&nbsp;Manuel Plaza","doi":"10.1039/d5qo00258c","DOIUrl":"10.1039/d5qo00258c","url":null,"abstract":"<div><div>This review highlights the use of photochemically excited electron donor–acceptor (EDA) complexes as a sustainable, modern approach to carbon–sulfur bond formation. C–S bonds are essential in various fields, including pharmaceuticals, materials science, and agrochemicals, yet traditional synthetic methods often face challenges such as harsh conditions and high costs. EDA complexes, formed through non-covalent interactions between electron-rich donors and electron-deficient acceptors, undergo visible-light-induced single-electron transfer (SET) to generate reactive radical intermediates. These intermediates enable efficient, selective, and environmentally friendly C–S bond formation under mild conditions. The article explores recent examples of practical applications of these reactions, including their mechanism, providing a comprehensive understanding of these cutting-edge methods and their potential to advance sustainable synthetic chemistry.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 13","pages":"Pages 3920-3941"},"PeriodicalIF":0.0,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143723998","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Electrochemical oxidative one-pot difunctionalization of diazo compounds with triazoles and nucleophiles† 重氮化合物与三唑和亲核试剂的电化学氧化一锅双官能化
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-28 DOI: 10.1039/d5qo00333d
Yaqi Deng , Jian Xue , Bajiba Bian , Shunying Liu
{"title":"Electrochemical oxidative one-pot difunctionalization of diazo compounds with triazoles and nucleophiles†","authors":"Yaqi Deng ,&nbsp;Jian Xue ,&nbsp;Bajiba Bian ,&nbsp;Shunying Liu","doi":"10.1039/d5qo00333d","DOIUrl":"10.1039/d5qo00333d","url":null,"abstract":"<div><div>Carbene radical coupling reactions are rarely developed due to their high reactivity. Here, we present a distinct electrochemical one-pot difunctionalization of diazo compounds with triazoles and nucleophiles. This method represents an effective strategy to access fully substituted triazole derivatives which can't be accessed using the known methods. This transformation exhibits synthetically useful yields and high regioselectivity, without the need for external chemical oxidants or metal catalysts. Furthermore, a variety of nucleophiles can be employed in this reaction to construct quaternary Csp<sup>3</sup>–N and Csp<sup>3</sup>–X (X = O/F) bonds. The reaction mechanism investigations show that this unprecedented pathway was promoted <em>via</em> a carbene radical coupling process followed by further oxidation and nucleophilic addition.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 13","pages":"Pages 3792-3798"},"PeriodicalIF":0.0,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143661084","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
meta-OTf-substituted diaryliodonium salts enabled aryne 1,2,2′-trifunctionalization via a cascade of thia-Fries and aza-Claisen rearrangements† 通过Thia-Fries级联和Aza-Claisen重排实现Aryne 1,2,2'-三官能化
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-28 DOI: 10.1039/d5qo00182j
Lifeng Chu , Huangguan Chen , Zhen-Jiang Xu , Limin Wang , Jianwei Han
{"title":"meta-OTf-substituted diaryliodonium salts enabled aryne 1,2,2′-trifunctionalization via a cascade of thia-Fries and aza-Claisen rearrangements†","authors":"Lifeng Chu ,&nbsp;Huangguan Chen ,&nbsp;Zhen-Jiang Xu ,&nbsp;Limin Wang ,&nbsp;Jianwei Han","doi":"10.1039/d5qo00182j","DOIUrl":"10.1039/d5qo00182j","url":null,"abstract":"<div><div>A novel cascade reaction involving thia-Fries and aza-Claisen rearrangements has been developed using <em>meta</em>-trifluoromethanesulfonate-substituted diaryliodonium salts, enabling the generation of aryne intermediates. In contrast to previously reported methods that achieve triple substitutions only on the aryne ring, our approach enables 1,2,2′-trisubstitution across two distinct aromatic rings of both the aryne and the aryl group of arylamines. The reaction efficiently forms C–N, C–S, and C–C bonds at adjacent positions of each aromatic ring in a sequential manner.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 13","pages":"Pages 3786-3791"},"PeriodicalIF":0.0,"publicationDate":"2025-03-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143635462","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Metal and photocatalyst-free alkylboration of [1.1.1]propellane enabled by red-light-induced electron transfer† 通过红光诱导的电子转移实现 [1.1.1]propellane 的无金属和无光催化剂烷基硼化
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00357a
Yuying Wang , Jianyang Dong , Yulin Xiao , Zhilin Wang , Weilin Wu , Dong Xue
{"title":"Metal and photocatalyst-free alkylboration of [1.1.1]propellane enabled by red-light-induced electron transfer†","authors":"Yuying Wang ,&nbsp;Jianyang Dong ,&nbsp;Yulin Xiao ,&nbsp;Zhilin Wang ,&nbsp;Weilin Wu ,&nbsp;Dong Xue","doi":"10.1039/d5qo00357a","DOIUrl":"10.1039/d5qo00357a","url":null,"abstract":"<div><div>Highly strained 1,3-disubstituted bicyclo[1.1.1]pentanes (BCPs) have emerged as bioisosteres of <em>para</em>-disubstituted benzene rings because of the ability of the former to impart valuable pharmacokinetic properties. However, challenges such as the lack of convenient and green access to useful BCP building blocks continue to hinder early-stage discovery research. Herein, we report a metal and photocatalyst-free method for deaminative borylation of [1.1.1]propellane for the synthesis of BCP boronates. This method involves the generation of alkyl or α-ester alkyl radicals <em>via</em> red-light-induced formation of a ternary electron donor–acceptor complex between a Katritzky salt, Cs<sub>2</sub>CO<sub>3</sub>, and B<sub>2</sub>pin<sub>2</sub>. Selective addition of the radicals to [1.1.1]propellane produces BCP radicals that undergo polarity-matched addition to B<sub>2</sub>pin<sub>2</sub>, leading to BCP difunctionalization. The method, which does not require metals or photocatalysts, allows for direct construction of alkyl species from readily available amines and α-amino acids and concurrent introduction of synthetically versatile pinacol boronate (Bpin) groups onto the BCP substructure. We demonstrate the synthetic utility of our method through several important transformations of the Bpin and hydroxyl functional groups of the products, including photoinduced cross-coupling reactions of BCP-BF<sub>3</sub>K derived from BCP-Bpin.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 4050-4057"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143775779","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Palladium-catalysed asymmetric regioselective hydroamination of dienoates† 钯催化的脂酸酯不对称区域选择性氢胺化反应
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00402k
Bao-Xin Liu , Xin-Ting Qin , Shi-Cun Li , Lei Zhu , Qin Ouyang , Wei Du , Ying-Chun Chen
{"title":"Palladium-catalysed asymmetric regioselective hydroamination of dienoates†","authors":"Bao-Xin Liu ,&nbsp;Xin-Ting Qin ,&nbsp;Shi-Cun Li ,&nbsp;Lei Zhu ,&nbsp;Qin Ouyang ,&nbsp;Wei Du ,&nbsp;Ying-Chun Chen","doi":"10.1039/d5qo00402k","DOIUrl":"10.1039/d5qo00402k","url":null,"abstract":"<div><div>Electron-deficient dienoates are occasionally utilised in hydrofunctionalisation reactions, and regioselectivity is a common concern. Here we report the palladium-catalysed enantioselective formal 1,4-Michael addition of pyrazoles to δ-aryl-substituted dienoates, proceeding through Pd<sup>0</sup> π-Lewis base-mediated protonation followed by regioselective asymmetric amination of the resultant π-allylpalladium species. Moreover, an intramolecular 1,5-addition-type reaction is realised under identical conditions by using δ-aryl-functionalised dienoates, affording indoline products enantioselectively.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 3998-4005"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143736333","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Thrysaxinones A–F: antibacterial phloroglucinol-terpenoid adducts from Thryptomene saxicola† 赤霉素A - F：从赤霉中提取的抗菌间苯三酚萜类加合物
Organic chemistry frontiers : an international journal of organic chemistry Pub Date : 2025-03-22 DOI: 10.1039/d5qo00172b
Wei-Fang Su , Ni-Ping Li , Rui-Qin Cui , Fen Liu , Mu Chen , Xin-Yue Wu , Min-Jing Cheng , Jia-Qing Cao , Wei Huang , Xiao-Qi Zhang , Wen-Cai Ye , Lei Wang
{"title":"Thrysaxinones A–F: antibacterial phloroglucinol-terpenoid adducts from Thryptomene saxicola†","authors":"Wei-Fang Su ,&nbsp;Ni-Ping Li ,&nbsp;Rui-Qin Cui ,&nbsp;Fen Liu ,&nbsp;Mu Chen ,&nbsp;Xin-Yue Wu ,&nbsp;Min-Jing Cheng ,&nbsp;Jia-Qing Cao ,&nbsp;Wei Huang ,&nbsp;Xiao-Qi Zhang ,&nbsp;Wen-Cai Ye ,&nbsp;Lei Wang","doi":"10.1039/d5qo00172b","DOIUrl":"10.1039/d5qo00172b","url":null,"abstract":"<div><div>Thrysaxinones A–F (), six new phloroglucinol-terpenoid adducts (PTAs), were isolated from <em>Thryptomene saxicola</em>. Their structures and absolute configurations were elucidated by extensive spectroscopic analysis, X-ray crystallography, and quantum chemical calculations. Compounds represent unprecedented PTAs with gorgonane- or oplopane-type sesquiterpenoid moieties. Notably, compound features an unusual 11-oxa-tricyclo[6.2.1.0<sup>4,9</sup>]undecane core. Compound is a unique PTA with a new carbon skeleton formed by an acylphloroglucinol unit coupled with a bicyclogermacrene-type sesquiterpenoid moiety. The plausible biogenetic pathways for compounds were proposed. Moreover, compounds , , , and exhibited significant antibacterial activities against clinical methicillin-resistant <em>Staphylococcus aureus</em> (MRSA) strains. Compound , the most potent one, could rapidly and effectively eradicate bacteria by inducing hyperpolarization and disrupting cell membrane integrity.</div></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"12 14","pages":"Pages 4037-4044"},"PeriodicalIF":0.0,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143767063","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","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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