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Recent advances in electrochemical deoxygenative functionalization of alcohols and their derivatives 醇及其衍生物电化学脱氧官能化的最新进展
Tetrahedron chem Pub Date : 2025-06-01 Epub Date: 2025-03-12 DOI: 10.1016/j.tchem.2025.100126
Yong Yuan, Lili Liu, Feng Zhang, Ya-Nan Zhang, Congde Huo
{"title":"Recent advances in electrochemical deoxygenative functionalization of alcohols and their derivatives","authors":"Yong Yuan,&nbsp;Lili Liu,&nbsp;Feng Zhang,&nbsp;Ya-Nan Zhang,&nbsp;Congde Huo","doi":"10.1016/j.tchem.2025.100126","DOIUrl":"10.1016/j.tchem.2025.100126","url":null,"abstract":"<div><div>This mini-review discusses the recent breakthroughs for electrochemical deoxygenative functionalization of alcohols and their derivatives. A diverse range of deoxygenative transformations is described, including the deoxygenative arylation, heteroarylation, alkylation, allylation, hydrogenation, cyanation, amination, borylation, and carboxylation. We hope that this mini-review can promote the rapid development in the field of electrochemical deoxygenative functionalization of alcohols and their derivatives.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100126"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143620354","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Total synthesis of the assigned structure of (+)-Maneolactenol （+）-马油酸醇配位结构的全合成
Tetrahedron chem Pub Date : 2025-06-01 Epub Date: 2025-03-13 DOI: 10.1016/j.tchem.2025.100127
Yidong Huang , Weiwu Ren
{"title":"Total synthesis of the assigned structure of (+)-Maneolactenol","authors":"Yidong Huang ,&nbsp;Weiwu Ren","doi":"10.1016/j.tchem.2025.100127","DOIUrl":"10.1016/j.tchem.2025.100127","url":null,"abstract":"<div><div>The first total synthesis of the assigned structure of (+)-maneolactenol, a marine natural product, has been completed in 7 steps. The pivotal transformations involve an asymmetric Diels-Alder reaction which serves as a key step in establishing stereochemistry, and the formation of core skeleton through iodolactonization. Particularly noteworthy are the selective reduction of acid to aldehyde and subsequent chelation-controlled stereoselective nucleophilic addition, facilitating the rapid and efficient assembly of side-chain motifs, as well as the selective reduction of the triple bond to <em>Z</em>-olefin moiety for the side chain construction. This strategy enabled the scalable synthesis of over 100 mg of the target compound, highlighting its practicality for larger-scale production.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100127"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143628787","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Efficient workflow for structural elucidation applied to solidagenone derivative: Combining the speed of ML-J-DP4 screening with the precision of DP4+ 高效的solidagenone衍生物结构解析工作流程：结合ML-J-DP4筛选的速度和DP4+的精度
Tetrahedron chem Pub Date : 2025-06-01 Epub Date: 2025-03-06 DOI: 10.1016/j.tchem.2025.100125
Iván Cortés , María Luz Tibaldi-Bollati , Viviana E. Nicotra , Manuela E. García , Ariel M. Sarotti
{"title":"Efficient workflow for structural elucidation applied to solidagenone derivative: Combining the speed of ML-J-DP4 screening with the precision of DP4+","authors":"Iván Cortés ,&nbsp;María Luz Tibaldi-Bollati ,&nbsp;Viviana E. Nicotra ,&nbsp;Manuela E. García ,&nbsp;Ariel M. Sarotti","doi":"10.1016/j.tchem.2025.100125","DOIUrl":"10.1016/j.tchem.2025.100125","url":null,"abstract":"<div><div>The derivatization of solidagenone through ring expansion, using the \"Complexity to Diversity\" synthetic strategy to obtain polyketones, yielded two products upon reaction of an intermediate with <em>in situ-</em>generated ruthenium tetroxide. As might happen, the spectroscopic and spectrometric data were inconclusive for the structural determination of one of these products. To address the issue, a ML-<em>J</em>-DP4//DP4+ workflow was studied, which allowed simultaneous determination of connectivity and relative configuration with high accuracy, while saving computational resources. Furthermore, during the calculation of NMR data at the DP4+ level, abnormally large errors were observed for the beta carbon of a polyhydroxylated conjugated enone. A literature analysis revealed that this behavior could be generalized, and after careful examination, it was determined to be the result of small geometric distortions caused by an overestimated network of intramolecular hydrogen bonds. To mitigate this common source of discrepancy, a heuristic solution was introduced as a proof of concept by <em>in silico</em> blocking of hydroxyl groups.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100125"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143644003","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Organocatalyzed asymmetric [2+2] cycloaddition of saccharin-derived endocyclic ketimines and allenoates for the synthesis of fused azetidines 糖精衍生的内环酮胺和烯丙酸酯的有机催化不对称[2+2]环加成合成融合氮杂啶
Tetrahedron chem Pub Date : 2025-06-01 Epub Date: 2025-05-10 DOI: 10.1016/j.tchem.2025.100133
Xinyu Liu , Yunfeng Zhang , Luning Zhou , Dehai Li , De Wang
{"title":"Organocatalyzed asymmetric [2+2] cycloaddition of saccharin-derived endocyclic ketimines and allenoates for the synthesis of fused azetidines","authors":"Xinyu Liu ,&nbsp;Yunfeng Zhang ,&nbsp;Luning Zhou ,&nbsp;Dehai Li ,&nbsp;De Wang","doi":"10.1016/j.tchem.2025.100133","DOIUrl":"10.1016/j.tchem.2025.100133","url":null,"abstract":"<div><div>We report a novel enantioselective [2 + 2] cycloaddition of allenoate and endocyclic ketimine derived from saccharin, catalyzed by a chiral tertiary amine. The methodology enables the synthesis of fused tricyclic azetidines with a quaternary stereogenic center, exhibiting high enantioselectivity and efficiency. The broad range of substrates demonstrate the generality of the protocol, and the resulting functional products can be easily converted into a variety of valuable synthons such as thiazepine derivatives.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100133"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143943551","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
Radical SAM cyclophane synthase catalyzes uniform cyclophane formation at multiple Trp-motifs 自由基SAM环烷合成酶催化在多个trp基序上形成均匀的环烷
Tetrahedron chem Pub Date : 2025-06-01 Epub Date: 2025-03-27 DOI: 10.1016/j.tchem.2025.100128
Abujunaid Habib Khan , Jabal Rahmat Haedar , Anitra Zīle , Chin-Soon Phan
{"title":"Radical SAM cyclophane synthase catalyzes uniform cyclophane formation at multiple Trp-motifs","authors":"Abujunaid Habib Khan ,&nbsp;Jabal Rahmat Haedar ,&nbsp;Anitra Zīle ,&nbsp;Chin-Soon Phan","doi":"10.1016/j.tchem.2025.100128","DOIUrl":"10.1016/j.tchem.2025.100128","url":null,"abstract":"<div><div>Cyclophane-containing products from ribosomally synthesized and post-translationally modified peptides (RiPPs) are generated by radical SAM cyclophane synthases (rSAM). In the past few years, rSAM enzymes that catalyze uniform cyclophanes at multiple Trp-motifs on the precursor peptides have been discovered more frequently. These enzymes install C–C or C–O cross-links at the three-residue motifs between Trp-C5/C6/C7 and an <em>sp</em><sup>3</sup> carbon side chain to generate strained macrocycles. This mini-review will focus on the rSAM enzymes, WprB, OscB, XncB, FwwB and RscB to summarize the biosynthesis and NMR characterization of Trp-containing cyclophane products, and promiscuity of these enzymes.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100128"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143738802","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Photoinduced enantioselective transformations via o-quinodimethane intermediates 通过邻喹诺二甲烷中间体的光诱导对映选择性转化
Tetrahedron chem Pub Date : 2025-06-01 Epub Date: 2025-04-16 DOI: 10.1016/j.tchem.2025.100131
Liwen Xia , Qingqin Huang , Zhao-Fei Zhang , Lei Dai
{"title":"Photoinduced enantioselective transformations via o-quinodimethane intermediates","authors":"Liwen Xia ,&nbsp;Qingqin Huang ,&nbsp;Zhao-Fei Zhang ,&nbsp;Lei Dai","doi":"10.1016/j.tchem.2025.100131","DOIUrl":"10.1016/j.tchem.2025.100131","url":null,"abstract":"<div><div>The effective stereoselective control of transient intermediates remains a formidable challenge in synthetic chemistry. <em>o</em>-Quinodimethane generated by photo-irradation has been extensively investigated and widely utilized as a nucleophilic surrogate. Nevertheless, enantioselective transformations involving <em>o</em>-quinodimethane are still underdeveloped, due to the persistent challenges in intercepting these intermediates and achieving effective stereoselective control with chiral catalysts. In this review, we summarize recent advances in photoinduced enantioselective reactions of <em>o</em>-quinodimethane, highlighting catalytic strategies, mechanistic insights, and current limitations in the field.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100131"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143847937","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
Fujiwara-Moritani reaction: challenges and new opportunities 藤原-森谷反应：挑战与新机遇
Tetrahedron chem Pub Date : 2025-06-01 Epub Date: 2025-04-18 DOI: 10.1016/j.tchem.2025.100130
Xiaojian Chen , Jun Zhang , Yang Gao, Qian Chen, Yanping Huo, Xianwei Li
{"title":"Fujiwara-Moritani reaction: challenges and new opportunities","authors":"Xiaojian Chen ,&nbsp;Jun Zhang ,&nbsp;Yang Gao,&nbsp;Qian Chen,&nbsp;Yanping Huo,&nbsp;Xianwei Li","doi":"10.1016/j.tchem.2025.100130","DOIUrl":"10.1016/j.tchem.2025.100130","url":null,"abstract":"<div><div>Fujiwara-Moritani reaction has proven to be robust for the efficient construction of polyfunctionalized olefins and cyclic skeletons. Recent advances toward greener systems, compatibility with strongly coordinating heterocycle substrates and sterically hindered internal olefins, and achieving asymmetric catalysis have collectively opened new frontiers for Fujiwara-Moritani reaction.2009 Elsevier Ltd. All rights reserved.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100130"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143860532","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
Synthetic nanographenes for cancer therapy 用于癌症治疗的合成纳米石墨烯
Tetrahedron chem Pub Date : 2025-06-01 Epub Date: 2025-04-22 DOI: 10.1016/j.tchem.2025.100132
Ranran Li, Chong-dao Lu, Peng An
{"title":"Synthetic nanographenes for cancer therapy","authors":"Ranran Li,&nbsp;Chong-dao Lu,&nbsp;Peng An","doi":"10.1016/j.tchem.2025.100132","DOIUrl":"10.1016/j.tchem.2025.100132","url":null,"abstract":"<div><div>Noninvasive cancer therapy, such as photodynamic therapy (PDT), photothermal therapy (PTT), and sonodynamic therapy (SDT) is becoming a promising option for cancer therapy. Being the most important factor, photosensitizer/sonosensitizer plays a pivotal role in the PDT, PTT, or SDT. Nanographenes (NGs), the large polycyclic aromatic hydrocarbons with nanoscale graphene structures, have received great attention. The significant efforts have been made by bottom-up synthesis strategy to prepare nanographenes with diverse structures and tunable properties. Notably, recent reports have suggested the NGs exhibit great potential as sensitizers for cancer therapy, which open up an avenue for the applications of NGs. In this review, we summarized these results by highlighting the synthesis of NG sensitizers and their efficiency in cancer therapy.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100132"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143864651","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
Catalytic asymmetric desymmetrization of diesters: advances and perspectives 二酯催化不对称脱对称：进展与展望
Tetrahedron chem Pub Date : 2025-06-01 Epub Date: 2025-05-14 DOI: 10.1016/j.tchem.2025.100134
Yu Huang, Jia-Yu Liao
{"title":"Catalytic asymmetric desymmetrization of diesters: advances and perspectives","authors":"Yu Huang,&nbsp;Jia-Yu Liao","doi":"10.1016/j.tchem.2025.100134","DOIUrl":"10.1016/j.tchem.2025.100134","url":null,"abstract":"<div><div>Catalytic asymmetric desymmetrization of prochiral and <em>meso</em>-diesters has emerged as a powerful strategy for the synthesis of chiral compounds featuring tertiary or quaternary stereogenic carbon centers. This mini-review summarizes the recent progress in this rapidly growing field. The reported fruitful examples have been organized and presented according to their reaction types. In the end, a perspective on the current limitations and future opportunities is provided to inspire further developments in this area.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"14 ","pages":"Article 100134"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144068276","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-free sulfenylation of pyrrolo[1,2-a]quinoxaline with diaryl disulfide facilitated by TBATB TBATB催化吡咯[1,2-a]喹啉与二硫酰基的无金属磺化反应
Tetrahedron chem Pub Date : 2025-03-01 Epub Date: 2025-01-24 DOI: 10.1016/j.tchem.2025.100123
Yingqian Li, Yali Liu, Yan Liu, Xiaowei Ma, Liang Xu, Ping Liu
{"title":"Metal-free sulfenylation of pyrrolo[1,2-a]quinoxaline with diaryl disulfide facilitated by TBATB","authors":"Yingqian Li,&nbsp;Yali Liu,&nbsp;Yan Liu,&nbsp;Xiaowei Ma,&nbsp;Liang Xu,&nbsp;Ping Liu","doi":"10.1016/j.tchem.2025.100123","DOIUrl":"10.1016/j.tchem.2025.100123","url":null,"abstract":"<div><div>A direct metal-free C1–H sulfenylation reaction of pyrrolo[1,2-<em>a</em>]quinoxaline with diaryl disulfides was developed at 50 °C using tetrabutylammonium tribromide (TBATB) as a promoter. Notably, raising the reaction temperature to 100 °C, TBATB played the dual role of both promoter and reactant, resulting in the simultaneous formation of C1–S bond and C3–Br bonds. The protocol has mild reaction conditions, broad substrate scope and good chemical and regioselectivity. In addition, the bifunctionalized reaction can be carried out smoothly at a gram-scale level, enabling the synthesis of structurally diverse pyrrolo[1,2-<em>a</em>]quinoxaline compounds.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"13 ","pages":"Article 100123"},"PeriodicalIF":0.0,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143182683","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
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