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Redox-Controlled Site-Specific O-Sulfation Facilitated Diversity-Oriented Chemoenzymatic Synthesis of Chondroitin Sulfates A/C/E and Chimeric Chondroitin Sulfates 氧化还原控制位点特异性o -硫酸促进了多样性导向的化学酶合成软骨素- insulates A/C/E和嵌合软骨素硫酸盐
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-05 DOI: 10.1021/acs.orglett.6c03858
Yan Zhang, Zhilin Zhang, Mengru Niu, Yaqi Wang, Kan Zhong, Haiyang Wu, Jinfeng Ye, Zhifei Hu, Saddam M. Muthana, Hongzhi Cao
{"title":"Redox-Controlled Site-Specific O-Sulfation Facilitated Diversity-Oriented Chemoenzymatic Synthesis of Chondroitin Sulfates A/C/E and Chimeric Chondroitin Sulfates","authors":"Yan Zhang,&nbsp;Zhilin Zhang,&nbsp;Mengru Niu,&nbsp;Yaqi Wang,&nbsp;Kan Zhong,&nbsp;Haiyang Wu,&nbsp;Jinfeng Ye,&nbsp;Zhifei Hu,&nbsp;Saddam M. Muthana,&nbsp;Hongzhi Cao","doi":"10.1021/acs.orglett.6c03858","DOIUrl":"10.1021/acs.orglett.6c03858","url":null,"abstract":"<p>The biological functions of chondroitin sulfate (CS)are stronglyinfluenced by its sulfation pattern. However, the limited site selectivityof currently available sulfotransferases has made it challenging toaccess CS oligosaccharides with diverse sulfation patterns. Herein,we report a redox-controlled site-specific O-sulfation strategy forthe programmable installation of CS-A, CS-C, or CS-E sequences atdefined positions along chondroitin backbones, enabling the diversity-orientedsynthesis of 28 structurally well-defined CS oligosaccharides withdistinct sulfation sequences.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"13052–13057"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088671","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Electrooxidative Ring-Opening and Strain-Release-Driven Skeletal Rearrangement of Cyclopropenes 环丙烯的电氧化打开和菌株释放驱动的骨架重排
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-05 DOI: 10.1021/acs.orglett.6c04062
Subhadeep Ghosh, Sumit Biswas, Suman Sekh, Indrajit Das
{"title":"Electrooxidative Ring-Opening and Strain-Release-Driven Skeletal Rearrangement of Cyclopropenes","authors":"Subhadeep Ghosh,&nbsp;Sumit Biswas,&nbsp;Suman Sekh,&nbsp;Indrajit Das","doi":"10.1021/acs.orglett.6c04062","DOIUrl":"10.1021/acs.orglett.6c04062","url":null,"abstract":"<p>We develop two distinct electrooxidative strategies forthe ring-openingand strain-release-driven rearrangement of cyclopropenes when reactingwith alcohols and trimethylsilyl azide, yielding <em>gem</em>-dialkoxyallylated compounds and tetrasubstituted alkenyl nitriles.The synthesis of allylated derivatives starts with the direct anodicoxidation of the cyclopropene ring to form a cyclopropene radicalcation. This radical cation undergoes addition by an alkoxide (actingas a nucleophile) at the C2 position, followed by regioselective cleavageof the C1–C2 bond. For alkenyl nitriles, anodic oxidation ofthe radical precursor produces an azide radical that adds to the cyclopropenering at the less-substituted C3 position. This leads to regioselectivecleavage of the C1–C3 bond. Additionally, the postreactionmodifications and the ability to synthesize deuterated allyl compoundsfurther demonstrate the utility of these transformations.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"13110–13115"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088722","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Catalytic Asymmetric Cyclopropanation of 1,1-Disubstituted Electron-Deficient Alkenes with Dimethyl Diazomalonate 二甲基重氮丙酸催化1,1-二取代缺电子烯烃的不对称环丙烷化
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-07 DOI: 10.1021/acs.orglett.6c03955
Charlotte Noël, Thomas Poisson, André B. Charette, Philippe Jubault
{"title":"Catalytic Asymmetric Cyclopropanation of 1,1-Disubstituted Electron-Deficient Alkenes with Dimethyl Diazomalonate","authors":"Charlotte Noël,&nbsp;Thomas Poisson,&nbsp;André B. Charette,&nbsp;Philippe Jubault","doi":"10.1021/acs.orglett.6c03955","DOIUrl":"10.1021/acs.orglett.6c03955","url":null,"abstract":"<p>The catalytic asymmetric synthesis of enantioenriched1,1-cyclopropanediesters is reported. A reaction combining Rh<sub>2</sub>(<em>R</em>-<em>p</em>-BTPCP)<sub>4</sub> as the chiral catalyst,dimethyl diazomalonate, and 1,1-disubstituted electron-poor alkeneswas developed, providing access to a broad range of tetrasubstitutedenantioenriched cyclopropanes. The reaction proceeded smoothly, andthe products were isolated in moderate to good yields with good toexcellent enantioselectivities.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"13076–13081"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149088579","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Rh-Catalyzed Cascade C–H Functionalization/Annulation of Ketimine Directed Arenes with Vinylcyclopropanes: Access to Bridged Azaheterocycles 铑催化氯胺酮导向芳烃与乙烯基环丙烷的级联C-H功能化/环化：桥杂环的获得
IF 4.7 1区 化学
Organic Letters Pub Date : 2026-10-16 Epub Date: 2026-10-07 DOI: 10.1021/acs.orglett.6c03868
Swati Samantaray, Sajal Roy, Mahesh Samantaray, Tharmalingam Punniyamurthy
{"title":"Rh-Catalyzed Cascade C–H Functionalization/Annulation of Ketimine Directed Arenes with Vinylcyclopropanes: Access to Bridged Azaheterocycles","authors":"Swati Samantaray,&nbsp;Sajal Roy,&nbsp;Mahesh Samantaray,&nbsp;Tharmalingam Punniyamurthy","doi":"10.1021/acs.orglett.6c03868","DOIUrl":"10.1021/acs.orglett.6c03868","url":null,"abstract":"<p>Rh-catalyzed cascadeC–H functionalization/annulation ofketimine-directed arenes with vinylcyclopropanes has been accomplishedto access <em>N</em>-bridged cyclic frameworks. The procedurecan be extended to vinylaziridine, vinyloxirane, and vinyl ethylenecarbonate to furnish spirotetrahydroisoquinoline and spiroindane scaffolds.The versatile reactivity of the vinyl strained rings, functional grouptolerance, and photophysical/molecular docking studies of the representativeexamples are the important practical features.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 41","pages":"13011–13016"},"PeriodicalIF":4.7,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149151323","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
SynergisticConstruction of High-Energy and Low-SensitivityEnergetic Materials via Ortho-Nitroamino and a Hydrazine Bridge 基于邻硝基氨基和联氨桥的高能低敏能材料协同构建
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-16 DOI: 10.1021/acs.orglett.6c03865
Zhiyan Zhang,Teng Zhu,Huailong Zhang,Caijin Lei,Deqi Wang,Jie Tang,Guangbin Cheng,Shuiping Zhou,Hongwei Yang
{"title":"Synergistic\u0000Construction of High-Energy and Low-Sensitivity\u0000Energetic Materials via Ortho-Nitroamino and a Hydrazine Bridge","authors":"Zhiyan Zhang,Teng Zhu,Huailong Zhang,Caijin Lei,Deqi Wang,Jie Tang,Guangbin Cheng,Shuiping Zhou,Hongwei Yang","doi":"10.1021/acs.orglett.6c03865","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03865","url":null,"abstract":"Abstract To achieve a balance between detonation performance and thermal stability, a synergistic strategy based on ortho-nitroamino groups and a hydrazine bridge was adopted in this work. Using this approach, compound 2 (6,6′-(hydrazine-1,2-diyl)bis(3,5-dinitropyridine-2,4-diamine)) and its perchlorate (3) and nitrate (4) salts were successfully synthesized via a one-step method in high yield. Notably, compound 3 shows a high thermal decomposition temperature (Td = 316 °C) which is comparable to that of HNS (Td = 318 °C), and its energy performance (Dv = 9135 m·s–1, Pe = 37.9 GPa) approaches that of HMX (Dv = 9144 m·s–1, P = 39.2 GPa). These results demonstrate the potential of compound 3 as a heat-resistant and insensitive explosive for practical applications. Furthermore, they highlight that the synergistic effect of hydrazine bridging and ortho-nitroamino groups holds promise for achieving a balance between high energy and low sensitivity.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"38 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209518","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Dialkylationof Vinyl Arenes under Cobalt Catalysis 钴催化下乙烯基芳烃的二烷基化反应
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-15 DOI: 10.1021/acs.orglett.6c03848
Jiabin Zhang,Yixuan Zhao,Dian Peng,Xiaonuo Shi,Shulei Ge,Qian Zhang,Jie Li
{"title":"Dialkylation\u0000of Vinyl Arenes under Cobalt Catalysis","authors":"Jiabin Zhang,Yixuan Zhao,Dian Peng,Xiaonuo Shi,Shulei Ge,Qian Zhang,Jie Li","doi":"10.1021/acs.orglett.6c03848","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03848","url":null,"abstract":"Abstract Herein, a directing group and ligand-free cobalt-catalyzed alkene dialkylation with various alkyl halides and alkylzinc pivalates is reported. This method is distinguished by its broad scope, synthetic simplicity, and excellent regio- and chemoselectivities, thus providing a modular platform for the rapid synthesis of C(sp3)-rich carbogenic skeletons via 2-fold C(sp3)–C(sp3)/C(sp3)–C(sp3) bond formation. Moreover, the controllable transformations with those polyhaloalkanes, such as simple C1 synthons of CF2Br2, CCl4, or CBr4, as well as their derivatives are of special interest, which should find potential applications in both synthetic and medicinal chemistry.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"22 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209557","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Palladium-CatalyzedEnantioselective Synthesis ofChiral Vinylallenes via γ-Selective Coupling of Vinylboronateswith Propargylic Carbonates 钯催化硼酸乙烯酯与碳酸丙酯γ-选择性偶联手性乙烯烯的对映选择性合成
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-15 DOI: 10.1021/acs.orglett.6c04246
Changwen Yan,Zixuan Liu,Chenyang Lu,Zheng Liu,Hui Zhang,Xiaoyu Wu
{"title":"Palladium-Catalyzed\u0000Enantioselective Synthesis of\u0000Chiral Vinylallenes via γ-Selective Coupling of Vinylboronates\u0000with Propargylic Carbonates","authors":"Changwen Yan,Zixuan Liu,Chenyang Lu,Zheng Liu,Hui Zhang,Xiaoyu Wu","doi":"10.1021/acs.orglett.6c04246","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04246","url":null,"abstract":"Abstract We report a palladium/phosphoramidite-catalyzed asymmetric γ-selective cross-coupling of racemic propargylic carbonates with alkenyl boronates for the synthesis of axially chiral vinylallenes. This transformation provides a direct and modular entry to densely substituted vinylallenes under mild conditions, furnishing the desired products in good to excellent yields and high enantioselectivities (up to 91% yield and 95% ee). A broad range of propargylic carbonates and cyclic, styrenyl, and functionalized alkenyl boronates are well tolerated. The synthetic utility of the method is demonstrated by a mmol-scale reaction and downstream transformations of the vinylallene products.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"14 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209520","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
EuphabeonesA–D, Rearranged Jatrophane Diterpenoidsfrom Euphorbia hylonoma : Isolation, Structural Elucidation,and Anti-Senescence Evaluation euphhabeonesa - d，重排麻风碱二萜：分离、结构解析和抗衰老评价
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-15 DOI: 10.1021/acs.orglett.6c04166
Shu-Qi Wu,Xian-Yuan Yang,Peng-Cheng Huang,Fang-Yu Yuan,Ming-Ju Wen,Wei-Ye Wu,Yun-yun Chen,Jia-Luo Huang,Gui-Hua Tang,Sheng Yin
{"title":"Euphabeones\u0000A–D, Rearranged Jatrophane Diterpenoids\u0000from\u0000 Euphorbia hylonoma\u0000 : Isolation, Structural Elucidation,\u0000and Anti-Senescence Evaluation","authors":"Shu-Qi Wu,Xian-Yuan Yang,Peng-Cheng Huang,Fang-Yu Yuan,Ming-Ju Wen,Wei-Ye Wu,Yun-yun Chen,Jia-Luo Huang,Gui-Hua Tang,Sheng Yin","doi":"10.1021/acs.orglett.6c04166","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04166","url":null,"abstract":"Abstract Euphabeones A–D (1–4), four rearranged jatrophane diterpenoids, were isolated from Euphorbia hylonoma. 1 and 2 possess a new 1(15→14),13(14→15)-diabeo-jatrophane skeleton featuring a 16-oxatricyclo[11.2.1.01,11]hexadecane core, while 3 and 4 are rare 1(15→14)-abeo-jatrophanes. Their structures were established by spectroscopic analysis, ECD calculation, and single-crystal X-ray diffraction. A plausible biosynthetic pathway for 1–4 was proposed and supported by biomimetic skeletal conversion. Compound 2 exhibited potent antisenescence activity, effectively ameliorating senescence phenotypes both in vitro and in vivo.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"11 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209525","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Convergent Approachfor the Asymmetric Synthesis ofVinyl Sulfoximines via Ruthenium-Catalyzed Enantioselective Alkylationof Sulfenamides with (Diazomethyl)phosphonates 钌催化亚砜胺与（重氮甲基）膦酸盐对映选择性烷基化合成乙烯基亚砜胺的会聚法
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-15 DOI: 10.1021/acs.orglett.6c04031
Zachary W. Boyer,Christopher W. Smith,Jonathan A. Ellman
{"title":"Convergent Approach\u0000for the Asymmetric Synthesis of\u0000Vinyl Sulfoximines via Ruthenium-Catalyzed Enantioselective Alkylation\u0000of Sulfenamides with (Diazomethyl)phosphonates","authors":"Zachary W. Boyer,Christopher W. Smith,Jonathan A. Ellman","doi":"10.1021/acs.orglett.6c04031","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c04031","url":null,"abstract":"Abstract The Ru(II)-(S)-tBu-Pheox-catalyzed enantioselective alkylation of sulfenamides with (diazomethyl)phosphonates proceeds in high yields typically with &amp;gt;90:10 er and at ≤1 mol % catalyst loading. A broad sulfenamide scope was observed, including (hetero)aryl S substituents with different steric and electronic characteristics as well as S-alkyl groups with different steric properties. Oxidation followed by the Horner–Wadsworth–Emmons reaction under mild conditions provides vinyl sulfoximines as exemplified by the asymmetric syntheses of sulfoximine analogues of two vinyl sulfone clinical candidates, K777 and recilisib.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"17 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209519","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 Chiral PhosphoricAcid Structure Leads to StrongInteractions That Affected Selectivity of the N-HydroxyalkylationReactions: A Density Functional Theory Study 手性磷酸结构导致影响n -羟基烷基化反应选择性的强相互作用：密度泛函理论研究
IF 5.2 1区 化学
Organic Letters Pub Date : 2026-10-15 DOI: 10.1021/acs.orglett.6c03162
Ran Zhang,ZiHao Li,ShuYu Zhang,Abing Duan
{"title":"A Chiral Phosphoric\u0000Acid Structure Leads to Strong\u0000Interactions That Affected Selectivity of the N-Hydroxyalkylation\u0000Reactions: A Density Functional Theory Study","authors":"Ran Zhang,ZiHao Li,ShuYu Zhang,Abing Duan","doi":"10.1021/acs.orglett.6c03162","DOIUrl":"https://doi.org/10.1021/acs.orglett.6c03162","url":null,"abstract":"Abstract Chiral phosphoric acids (CPAs) can regulate reaction selectivity via catalyst–substrate noncovalent interactions (NCIs). Most studies remain macroscopic and have not addressed how CPA structures modulate the interaction strength and thereby selectivity. This study reveals that, in CPA-catalyzed N-hydroxyalkylation reactions, the CPA backbone rigidity and substituent structure promote stronger interactions, thereby enhancing enantioselectivity. An ordered π system facilitates the formation of more pronounced π–π stacking.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"64 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2026-10-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"149209526","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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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