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Indium-catalyzed formal [4 + 1 + 1]/[4 + 1] isocyanide-based annulation for construction of polyfunctionalized pyrano- and furoquinolines. 铟催化的[4 + 1 + 1]/[4 + 1]异氰酸酯环化反应用于多功能化吡喃和呋喃喹啉的合成。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-16 DOI: 10.1039/d5ob00512d
Issa Zarei, Hormoz Khosravi, Frank Rominger, Leila Rezaei Somee, Saeed Balalaie
{"title":"Indium-catalyzed formal [4 + 1 + 1]/[4 + 1] isocyanide-based annulation for construction of polyfunctionalized pyrano- and furoquinolines.","authors":"Issa Zarei, Hormoz Khosravi, Frank Rominger, Leila Rezaei Somee, Saeed Balalaie","doi":"10.1039/d5ob00512d","DOIUrl":"https://doi.org/10.1039/d5ob00512d","url":null,"abstract":"<p><p>A distinctive catalytic reaction involving multiple isocyanide insertions on ambiphilic quinolines has been introduced to synthesize intricate polyheterocyclic scaffolds (21 examples, up to 71% yield) through the formation of several C-C, C-O, and C-N bonds. Our findings indicate that these reactions can switch between two cycloadditions ([4 + 1 + 1] and [4 + 1]) depending on the isocyanide structure and the solvent used. Finally, furo[2,3-<i>b</i>]quinoline-2,3-diamine examples, as some of the novel products, exhibit strong solvatochromism in various solvents.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144075117","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
Triflic acid catalyzed intermolecular hydroamination of alkenes with Fmoc-NH2 as the amine source. 以Fmoc-NH2为胺源，三酸催化烯烃分子间氢胺化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-15 DOI: 10.1039/d5ob00519a
Aswathi C S, Chinraj Sivarajan, Raja Mitra
{"title":"Triflic acid catalyzed intermolecular hydroamination of alkenes with Fmoc-NH<sub>2</sub> as the amine source.","authors":"Aswathi C S, Chinraj Sivarajan, Raja Mitra","doi":"10.1039/d5ob00519a","DOIUrl":"https://doi.org/10.1039/d5ob00519a","url":null,"abstract":"<p><p>Intermolecular hydroamination of alkenes is recognized as one of the most challenging synthetic pathways for directly obtaining primary amine derivatives from alkenes. While metal-catalyzed hydroamination is well established, metal-free hydroamination for synthesizing primary amines remains an attractive yet infrequent approach. In this study, we report the hydroamination of vinyl arenes using triflic acid as the catalyst and Fmoc-NH<sub>2</sub> as the amine source. The optimized conditions proved effective for a range of vinyl arenes and some endocyclic alkenes, yielding moderate to excellent results (40-91%). Mechanistic investigations conducted through NMR, variable temperature NMR, kinetic studies, and control reactions indicated that the transient interaction between triflic acid and Fmoc-NH<sub>2</sub> inhibited styrene polymerization. Primary amines were obtained by deprotecting the Fmoc group using KOH/MeOH.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144075044","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
Competition and cooperation between steric hindrance and hydrogen bonding of supramolecular discs. 超分子圆盘的空间位阻与氢键的竞争与合作。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-14 DOI: 10.1039/d5ob00609k
Yuhei Yamada, Shunsuke Kakinuma, Hiroki Hanayama, Sougata Datta, Shiki Yagai
{"title":"Competition and cooperation between steric hindrance and hydrogen bonding of supramolecular discs.","authors":"Yuhei Yamada, Shunsuke Kakinuma, Hiroki Hanayama, Sougata Datta, Shiki Yagai","doi":"10.1039/d5ob00609k","DOIUrl":"https://doi.org/10.1039/d5ob00609k","url":null,"abstract":"<p><p>We previously reported supramolecular polymers formed by π-π stacking between disc-shaped hexamers (rosettes) of barbituric acid-functionalized π-conjugated molecules. Herein, we investigated the impact of amide-mediated hydrogen bonding along two types of polymer backbones formed by distinct stacking of rosettes. The stabilization of the hydrogen bonds strongly depends on the intrinsic stacking arrangement of rosettes, which competes with the amide hydrogen-bonding.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143953108","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
Recent advances in the synthesis of bicyclo[4.1.1]octanes. 双环[4.1.1]辛烷的合成研究进展。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-14 DOI: 10.1039/d5ob00533g
Jianyang Dong, Dejiang Yu, Ting Li, Dong Xue
{"title":"Recent advances in the synthesis of bicyclo[4.1.1]octanes.","authors":"Jianyang Dong, Dejiang Yu, Ting Li, Dong Xue","doi":"10.1039/d5ob00533g","DOIUrl":"https://doi.org/10.1039/d5ob00533g","url":null,"abstract":"<p><p>The exploration of bicyclo[<i>n</i>.1.1]alkanes, known for their intricate chemical diversity and potential as benzene bioisosteres, has garnered significant attention over the past two decades. In particular, the past year has seen the emergence of bicyclo[4.1.1]octanes and their structural analogues as promising bioisosteres for <i>meta</i>-substituted arenes and <i>cis</i>-1,3-disubstituted cyclohexanes. To meet the growing demand for bicyclo[4.1.1]octanes, chemists have recently developed innovative (4 + 3) cycloaddition strategies, leveraging bicyclobutanes (BCBs) and 1,4-dipoles for their synthesis. This review provides a comprehensive evaluation of recent advancements in the synthesis and functionalization of these compounds, emphasizing their scope and underlying mechanisms. Additionally, we highlight the challenges and future prospects of identifying novel reaction pathways to access new functionalized bicyclo[4.1.1]octanes.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143957345","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 natural products via conjugated ynone intermediates: a new millennium update. 通过共轭炔中间体的天然产物的全合成：一个新的千年更新。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-14 DOI: 10.1039/d5ob00524h
Sunita Bhagat, Nikita Goel, Poonam Kumari, Gunjan, Ananya Khullar
{"title":"Total synthesis of natural products <i>via</i> conjugated ynone intermediates: a new millennium update.","authors":"Sunita Bhagat, Nikita Goel, Poonam Kumari, Gunjan, Ananya Khullar","doi":"10.1039/d5ob00524h","DOIUrl":"https://doi.org/10.1039/d5ob00524h","url":null,"abstract":"<p><p>Natural products play a vital role in both medicinal chemistry and industrial chemistry due to their unique structural diversity, biological activity, and ability to serve as precursors for the development of therapeutic agents, materials, and chemicals. Drug discovery has always been influenced by natural compounds, which have served as the basis for many medicinal compounds. Ynones, or α,β-acetylenic ketones, are valuable intermediates in organic synthesis and have been used to prepare a variety of natural products and bioactive compounds due to their exceptional reactivity and adaptability. Ynones not only are integral to the biosynthesis of certain natural products but also serve as crucial building blocks in synthetic chemistry due to their ability to undergo various reactions, such as Michael addition and cycloaddition, which can lead to a wide array of structural motifs with diverse biological activities. These substances make it possible for atom-economical processes like cyclizations and rearrangements to produce intricate molecular structures with improved pharmacological characteristics. The synthetic methods developed using ynones from 2005 to 2024 are discussed in this review, with a focus on innovative and environmentally conscious methods of producing natural compounds. Their critical role in medicinal chemistry is highlighted through insights into developments and future directions.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143955461","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
Cytotoxic polyketides from the desert soil-derived fungus Preussia fleischhakii H231. 荒漠土壤真菌Preussia fleischhakii H231的细胞毒聚酮。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-14 DOI: 10.1039/d5ob00494b
Xiaomei Song, Yu Li, Weikang Li, Tianxiang Zhang, Yuexun Luo, Meng Ren, Duqiang Luo, Vuanghao Lim
{"title":"Cytotoxic polyketides from the desert soil-derived fungus <i>Preussia fleischhakii</i> H231.","authors":"Xiaomei Song, Yu Li, Weikang Li, Tianxiang Zhang, Yuexun Luo, Meng Ren, Duqiang Luo, Vuanghao Lim","doi":"10.1039/d5ob00494b","DOIUrl":"https://doi.org/10.1039/d5ob00494b","url":null,"abstract":"<p><p>Three new heterodimeric polyketides, fleisine A-C (1-3), were obtained from the fermentation product of the desert soil-derived fungus <i>Preussia fleischhakii</i> H231. The structures of 1-3 were elucidated through an integrated analysis of spectroscopic data, while the absolute configurations were established by chemical hydrolysis followed by calculated electronic circular dichroism (ECD). Biological evaluation revealed that compounds 1 and 2 exhibited potent cytotoxicity against multiple human tumor cell lines. The IC<sub>50</sub> values ranged between 2.3 and 25.2 μM. Further <i>in vitro</i> assays demonstrated that compounds 1 and 2 significantly suppressed the proliferation and migration of gastric adenocarcinoma cells (SGC-7901 and MGC-803) dose-dependently. These findings demonstrate the potential of 1 and 2 as favorable candidates for further anticancer drug development.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143953190","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
Synthesis of 3-indolyl all-carbon quaternary centers via Rh/Brønsted acid co-catalyzed three-component reactions of azoalkenes with indoles and diazoacetates. Rh/Brønsted酸催化偶氮烯烃与吲哚和重氮乙酸酯三组分反应合成3-吲哚基全碳季中心
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-14 DOI: 10.1039/d5ob00567a
Xiao-Jing Yue, Li-Ping Pei, Min-Can Wang, Shi-Kun Jia, Guang-Jian Mei
{"title":"Synthesis of 3-indolyl all-carbon quaternary centers <i>via</i> Rh/Brønsted acid co-catalyzed three-component reactions of azoalkenes with indoles and diazoacetates.","authors":"Xiao-Jing Yue, Li-Ping Pei, Min-Can Wang, Shi-Kun Jia, Guang-Jian Mei","doi":"10.1039/d5ob00567a","DOIUrl":"https://doi.org/10.1039/d5ob00567a","url":null,"abstract":"<p><p>Highly diastereoselective three-component reactions of azoalkenes with indoles and diazoacetates have been developed <i>via</i> a Rh/Brønsted acid co-catalyzed strategy. These transformations provide efficient construction of a range of 3-indolyl all-carbon quaternary centers in good yields and diastereoselectivities. This reaction is proposed to proceed through Michael-type trapping of zwitterionic intermediates generated from metal carbenes and indoles.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143956610","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
Rhodium-catalyzed isomerization of homoallylic alcohols with a tethered carbonyl group: pathway to 1,6-diketones. 铑催化的含拴链羰基的同丙烯醇异构化：1,6-二酮的途径。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-14 DOI: 10.1039/d5ob00473j
Shuang Peng, Tong Su, Xuan Yang, Jia-Jie Li, Jie Wan, Hai-Liang Ni, Peng Cao, Ping Hu, Bi-Qin Wang, Bin Chen
{"title":"Rhodium-catalyzed isomerization of homoallylic alcohols with a tethered carbonyl group: pathway to 1,6-diketones.","authors":"Shuang Peng, Tong Su, Xuan Yang, Jia-Jie Li, Jie Wan, Hai-Liang Ni, Peng Cao, Ping Hu, Bi-Qin Wang, Bin Chen","doi":"10.1039/d5ob00473j","DOIUrl":"https://doi.org/10.1039/d5ob00473j","url":null,"abstract":"<p><p>Herein, we report a rhodium-catalyzed isomerization of homoallylic alcohols with a tethered carbonyl group to synthesize structurally diverse unsymmetrical 1,6-diketones with atom, step, and redox economy. By introducing chiral ligands, good enantioselective isomerization products can be obtained. The utility of this reaction was also demonstrated with diverse transformations.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143953556","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 cross-coupling of sterically encumbered aryl Grignard reagents with allylic bromides: application to the synthesis of cannabigerol. 铁催化空间负载芳基格氏试剂与烯丙基溴的交叉偶联：在大麻酚合成中的应用。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-14 DOI: 10.1039/d5ob00442j
Mao-Qi Yang, Pan Ren, Jian-Guo Fu, Chen-Guo Feng
{"title":"Iron-catalyzed cross-coupling of sterically encumbered aryl Grignard reagents with allylic bromides: application to the synthesis of cannabigerol.","authors":"Mao-Qi Yang, Pan Ren, Jian-Guo Fu, Chen-Guo Feng","doi":"10.1039/d5ob00442j","DOIUrl":"https://doi.org/10.1039/d5ob00442j","url":null,"abstract":"<p><p>This study presents an iron-catalyzed cross-coupling platform that addresses the persistent challenge of coupling sterically hindered <i>ortho</i>,<i>ortho</i>-disubstituted aryl Grignard reagents with allyl bromides. Using TMU as a high performance, low loading ligand, the system achieves excellent yields on bulky substrates. The methodology demonstrates good functional group compatibility and preserves ester moieties for downstream derivatization. Scalability is confirmed by multigram-scale synthesis. Successful conversion to cannabigerol validates practical utility in natural product synthesis.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143951921","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
Pd(II)-catalyzed regioselective hydroarylation of allenyl-containing α-amino acid derivatives with aryl boronic acids. Pd（II）催化含烯丙基α-氨基酸衍生物与芳基硼酸的区域选择性氢芳基化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2025-05-13 DOI: 10.1039/d5ob00622h
Alexandra S Bubnova, Anna N Philippova, Pavel S Gribanov, Alexander F Smol'yakov, Sergey N Osipov, Daria V Vorobyeva
{"title":"Pd(II)-catalyzed regioselective hydroarylation of allenyl-containing α-amino acid derivatives with aryl boronic acids.","authors":"Alexandra S Bubnova, Anna N Philippova, Pavel S Gribanov, Alexander F Smol'yakov, Sergey N Osipov, Daria V Vorobyeva","doi":"10.1039/d5ob00622h","DOIUrl":"https://doi.org/10.1039/d5ob00622h","url":null,"abstract":"<p><p>A convenient pathway to a new family of α,α-disubstituted α-amino acid derivatives bearing an aryl alkene moiety at the side chain has been developed. This method is based on hydroarylation of functional allenes with aryl boronic acids under Pd(II)/dppf catalysis. The studied reactions represent the first example of the metal-catalyzed arylation of allenyl-containing α-amino acid derivatives and allow for the efficient assembly of biologically valuable molecules under mild conditions in good yields and high regio- and stereoselectivity.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.9,"publicationDate":"2025-05-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143956222","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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