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Tamaru reaction-based approach towards the synthesis of muscone and analogues using renewable sources
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-18 DOI: 10.1016/j.tetlet.2025.155593
Santosh J. Gharpure, Saidurga Prasad Kommyreddy
{"title":"Tamaru reaction-based approach towards the synthesis of muscone and analogues using renewable sources","authors":"Santosh J. Gharpure,&nbsp;Saidurga Prasad Kommyreddy","doi":"10.1016/j.tetlet.2025.155593","DOIUrl":"10.1016/j.tetlet.2025.155593","url":null,"abstract":"<div><div>Muscone is considered as the king of fragrances, due to its rare occurrence and exotic nature, many attempts have been made to synthesise musk analogues. The presence of methyl group at the C-3 position from ketone imparts the musk character to the molecule. The Tamaru reaction (Ni-catalysed reductive coupling of aldehyde and 1,3-dienes) is used as the key step for the installation of the methyl group in an efficient manner to afford the RCM precursor diene. A short three step sequence involving oxidation, RCM and reduction gave a highly efficient access to muscone and analogues. Both the precursors, namely, the aldehyde and isoprene are derived from renewable resource.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"163 ","pages":"Article 155593"},"PeriodicalIF":1.5,"publicationDate":"2025-04-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143844459","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Improved synthesis of bioactive L-penicillamine via an economical and environment-friendly route
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-11 DOI: 10.1016/j.tetlet.2025.155573
Zhenxiang Liu , Lingli Shao , Shuping Cai , Chaoqun Bian , Haojie Zhu , Xuanang Shen , Hangcheng Ni , Ling Wang , Kaichuan Yang , Hui Mao
{"title":"Improved synthesis of bioactive L-penicillamine via an economical and environment-friendly route","authors":"Zhenxiang Liu ,&nbsp;Lingli Shao ,&nbsp;Shuping Cai ,&nbsp;Chaoqun Bian ,&nbsp;Haojie Zhu ,&nbsp;Xuanang Shen ,&nbsp;Hangcheng Ni ,&nbsp;Ling Wang ,&nbsp;Kaichuan Yang ,&nbsp;Hui Mao","doi":"10.1016/j.tetlet.2025.155573","DOIUrl":"10.1016/j.tetlet.2025.155573","url":null,"abstract":"<div><div>An economical and environment-friendly synthetic route was developed toward L-penicillamine (L-H<sub>2</sub>pen) in concise 8-step from commercially available and inexpensive Penicillin G potassium salt. Ordinary reagents such as acetone, ethanol, triethylamine, L(+)-Tartaric acid etc. are used and no special catalysts applied in whole process. Acetone used in step 2 and D-penicillamine (D-H<sub>2</sub>pen) produced from resolving process could be recycled after appropriate working up. The total yield of L-H<sub>2</sub>pen reached around 20 % based on the starting materials. No chromatographic separations were utilized in the new protocol which seems amenable to scale-up.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"163 ","pages":"Article 155573"},"PeriodicalIF":1.5,"publicationDate":"2025-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143828361","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Visible light-induced perfluoroalkylation reaction of indoles in the presence of Na2-eosin Y
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-11 DOI: 10.1016/j.tetlet.2025.155571
Xiang-Wu He , Chen Du , Zhen-Jiang Liu , Min Jiang , Jin-Tao Liu
{"title":"Visible light-induced perfluoroalkylation reaction of indoles in the presence of Na2-eosin Y","authors":"Xiang-Wu He ,&nbsp;Chen Du ,&nbsp;Zhen-Jiang Liu ,&nbsp;Min Jiang ,&nbsp;Jin-Tao Liu","doi":"10.1016/j.tetlet.2025.155571","DOIUrl":"10.1016/j.tetlet.2025.155571","url":null,"abstract":"<div><div>Visible light-induced perfluoroalkylation reaction of 3-substituted indoles using Na<sub>2</sub>-Eosin Y as photoredox catalysis was achieved under mild conditions to give a series of C2-perfluoroalkylated indoles in moderate to good yields. Under similar conditions, both C3 and C4 perfluoroalkylation reactions of 2-substituted indoles occurred to produce two regioisomers. The reaction of unsubstituted indole gave the C2 and C3 perfluoroalkylation products. A possible pathway was proposed based on the experimental results.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"162 ","pages":"Article 155571"},"PeriodicalIF":1.5,"publicationDate":"2025-04-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143817381","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Brønsted-acid-mediated cyclocondensation towards dihydro-1-benzazepines
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-10 DOI: 10.1016/j.tetlet.2025.155572
Letian Xu, Alena M. Vasquez, Jose M. Medina, Juntao Sun, Keary M. Engle
{"title":"Brønsted-acid-mediated cyclocondensation towards dihydro-1-benzazepines","authors":"Letian Xu,&nbsp;Alena M. Vasquez,&nbsp;Jose M. Medina,&nbsp;Juntao Sun,&nbsp;Keary M. Engle","doi":"10.1016/j.tetlet.2025.155572","DOIUrl":"10.1016/j.tetlet.2025.155572","url":null,"abstract":"<div><div>A Brønsted-acid-mediated cyclocondensation of 2-alkenylanilines and (hetero)arylethanones to access dihydro-1-benzazepines is reported. Various 2-alkenylanilines and electron-deficient (hetero)arylethanones are tolerated and afford moderate to good yields. Coordination of 2-pyridinyl-substituted dihydro-1-benzazepines to palladium(II) demonstrates their ability to serve as novel N,N-bidentate ligand scaffolds. Isotope labeling and reactivity trends are consistent with an aza-8π-electrocyclization mechanism for this medium-sized ring-forming reaction.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"162 ","pages":"Article 155572"},"PeriodicalIF":1.5,"publicationDate":"2025-04-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143817382","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Metal-free regioselective ring expansion reaction of acenaphthenequinone with diazomethanes: A facile one-pot synthesis of phenalenones
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-08 DOI: 10.1016/j.tetlet.2025.155559
Xiaohan Jin , Na Gao , Bingwei Hu , Mei Chen , Yan Zheng , Bingfei Shi , Wenhui Ma , Yiren Xu , Jianqiang Zhang
{"title":"Metal-free regioselective ring expansion reaction of acenaphthenequinone with diazomethanes: A facile one-pot synthesis of phenalenones","authors":"Xiaohan Jin ,&nbsp;Na Gao ,&nbsp;Bingwei Hu ,&nbsp;Mei Chen ,&nbsp;Yan Zheng ,&nbsp;Bingfei Shi ,&nbsp;Wenhui Ma ,&nbsp;Yiren Xu ,&nbsp;Jianqiang Zhang","doi":"10.1016/j.tetlet.2025.155559","DOIUrl":"10.1016/j.tetlet.2025.155559","url":null,"abstract":"<div><div>Herein, we describe a regioselective ring-expansion reaction of acenaphthenequinone using N-tosylhydrazone as diazo 1,3-dipolar precursor, which can highly efficiently prepare functionalized 3-phenylphenalenones in ethanol solvent. These reactions feature readily available starting materials, transition metal- and oxidant-free, Ecofriendly operations, one-pot syntheses and wide functional group tolerance. Specifically, in the synthesized phenalenones, C-2 and C-3 are substituted by hydroxyl and phenyl has not been reported so far, and the potential biological and physical value of these newly synthesized corresponding products has good application foreground.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"162 ","pages":"Article 155559"},"PeriodicalIF":1.5,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143791444","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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 and PEGylation of a novel, per-6-substituted propargyl sulfonamide β-cyclodextrin
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-08 DOI: 10.1016/j.tetlet.2025.155592
Thomas K. Green
{"title":"Synthesis and PEGylation of a novel, per-6-substituted propargyl sulfonamide β-cyclodextrin","authors":"Thomas K. Green","doi":"10.1016/j.tetlet.2025.155592","DOIUrl":"10.1016/j.tetlet.2025.155592","url":null,"abstract":"<div><div>A novel single isomer, per-6-substituted alkyne-terminated sulfonamide β-cyclodextrin (β-CD) was synthesized, in two steps, from heptakis-2,3-<em>O</em>-dimethyl-6-O-sulfobutyl-β-CD, sodium salt. The intermediate sulfonamide β-CD was then per-6-PEGylated in a third step with azide-terminated polyethylene glycols (N<sub>3</sub>-PEG<sub>5</sub>-OH and N<sub>3</sub>-PEG<sub>47</sub>-OCH<sub>3</sub>) by copper-catalyzed azide-alkyne cycloaddition (CuAAC) The described derivatization strategy is the first to exploit the reactivity of sulfonate functions of sulfobutylether (SBE) anionic cyclodextrins, and results in a water-soluble, single isomer PEG-triazole-sulfonamide β-CD with an extended hydrophobic cavity.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"162 ","pages":"Article 155592"},"PeriodicalIF":1.5,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143821008","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Microwave-assisted one-pot synthesis of fused isoxazolo[4′,5′:3,4]pyrrolo[1,2-c]pyrimidines as potent anticancer agents: In vitro and in silico study
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-08 DOI: 10.1016/j.tetlet.2025.155570
Raveendar Reddy Thatikonda, Karuna Sree Merugu
{"title":"Microwave-assisted one-pot synthesis of fused isoxazolo[4′,5′:3,4]pyrrolo[1,2-c]pyrimidines as potent anticancer agents: In vitro and in silico study","authors":"Raveendar Reddy Thatikonda,&nbsp;Karuna Sree Merugu","doi":"10.1016/j.tetlet.2025.155570","DOIUrl":"10.1016/j.tetlet.2025.155570","url":null,"abstract":"<div><div>Microwave-aided one-pot synthesis of certain fused isoxazolo[4′,5′:3,4]pyrrolo[1,2-<em>c</em>] pyrimidine derivatives are synthesized using one-pot Cu(I)-catalyzed [3+2]cycloaddition, followed by Pd-catalyzed C<img>C bond coupling between iodoalkyne and freshly prepared nitrile oxides in a recyclable ionic liquid [Emim]BF<sub>4</sub>. The anticancer efficacy of the synthesized isoxazoles was then tested <em>in vitro</em> against A-459 and NCI-H460 cancer cell lines, and some compounds (<strong>5k</strong>–<strong>5n</strong>) demonstrated more activity than the others, with <strong>5k</strong> and <strong>5l</strong> acting more potently than the standard drugs, 5-FU and erlotinib. We also detected EGFR inhibitory activity in the potent compounds <strong>5k</strong>, <strong>5l</strong>, <strong>5m</strong>, and <strong>5n</strong>, and the results revealed that compound <strong>5m</strong> had the highest inhibitory action compared to the other compounds and was comparable to erlotinib. We also performed <em>in silico</em> tests to assess the molecular interactions of more powerful compounds with EGFR protein (PDB: <span><span>4HJO</span><svg><path></path></svg></span>). Our findings indicated that all potent compounds had stronger binding interactions than standard erlotinib (−7.69 kcal/mol), with binding energies ranging from −8.41 to −9.26 kcal/mol.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"162 ","pages":"Article 155570"},"PeriodicalIF":1.5,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143791403","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Syntheses of C22–C29 and C20–C29 sections of amphidinol 3
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-08 DOI: 10.1016/j.tetlet.2025.155586
Yuki Yamashita, Yuma Wakamiya, Yusuke Mita, Yoko Yasuno, Tohru Oishi
{"title":"Syntheses of C22–C29 and C20–C29 sections of amphidinol 3","authors":"Yuki Yamashita,&nbsp;Yuma Wakamiya,&nbsp;Yusuke Mita,&nbsp;Yoko Yasuno,&nbsp;Tohru Oishi","doi":"10.1016/j.tetlet.2025.155586","DOIUrl":"10.1016/j.tetlet.2025.155586","url":null,"abstract":"<div><div>Polyol segments corresponding to C22–C29 and C20–C29 sections of amphidinol 3 (AM3) were synthesized as building blocks of artificial analogues of AM3 for structure–activity relationship studies. The C22–C29 section was synthesized from (<em>S</em>)-Roche ester through continuous half-reduction of an ester and a Grignard reaction under flow and batch conditions, followed by iterative ozonolysis and Grignard reactions. The C20–C29 section was derived from the common intermediate of AM3 and the artificial analogue corresponding to the C21–C67 section via olefination and Sharpless asymmetric dihydroxylation.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"162 ","pages":"Article 155586"},"PeriodicalIF":1.5,"publicationDate":"2025-04-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143826258","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Bis-dispiro-indolinone-pyrrolidine-imidazolones with polymethylene linkers between imidazolone fragments
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-05 DOI: 10.1016/j.tetlet.2025.155589
V.S. Polyakov, E.V. Pervakova, Yu.K. Grishin, E.K. Beloglazkina
{"title":"Bis-dispiro-indolinone-pyrrolidine-imidazolones with polymethylene linkers between imidazolone fragments","authors":"V.S. Polyakov,&nbsp;E.V. Pervakova,&nbsp;Yu.K. Grishin,&nbsp;E.K. Beloglazkina","doi":"10.1016/j.tetlet.2025.155589","DOIUrl":"10.1016/j.tetlet.2025.155589","url":null,"abstract":"<div><div>A method for the synthesis of bis-(dispiro-imidazolone-pyrrolidine-indolinones) in which spirocyclic fragments are linked by C4, C6 and C8 alkyl linkers between the N(3) nitrogen atoms of the imidazolone ring has been proposed. A two-step synthetic sequence was used for the synthesis, consisting of the interaction of α,ω-dialkylamines with ethyl isothiocyanatoacetate, followed by the reaction of the intermediate bis-thioureas with substituted benzaldehydes to produce bis-arylidenetiohydantoins and the final 1,3-dipolar cycloaddition of azomethine ylides generated in situ from isatins and <em>N</em>-methylglycine.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"162 ","pages":"Article 155589"},"PeriodicalIF":1.5,"publicationDate":"2025-04-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143807141","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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
Alkylidene transfer reactions from nitrones to iminoiodanes
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-04 DOI: 10.1016/j.tetlet.2025.155558
Noriko Okamoto, Haruto Ogino, Takuya Sueda
{"title":"Alkylidene transfer reactions from nitrones to iminoiodanes","authors":"Noriko Okamoto,&nbsp;Haruto Ogino,&nbsp;Takuya Sueda","doi":"10.1016/j.tetlet.2025.155558","DOIUrl":"10.1016/j.tetlet.2025.155558","url":null,"abstract":"<div><div>Herein, we report a reaction involving alkylidene transfer from nitrones to iminoiodanes. The alkylidene moiety is transferred from the nitrone to the imido group of the iminoiodane accompanied by cleavage of the nitrone C<img>N bond to deliver a nitroso compound and an imine. When an excess of the iminoiodane is used at higher temperature, the iminoiodane reacts with the nitroso compound to form an azoxy sulfone. We also found that an azomethine imine can be used as an alkylidene transfer agent.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"161 ","pages":"Article 155558"},"PeriodicalIF":1.5,"publicationDate":"2025-04-04","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143768829","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"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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