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Photoinduced radical CH alkylation by sulfoxonium, sulfonium, selenium and pyridinium ylides as new HAT organocatalysts 亚砜、磺、硒和吡啶类化合物作为新型HAT有机催化剂的光诱导自由基CH烷基化反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-06 DOI: 10.1016/j.tetlet.2025.155590
Shuwen Chen , Hui Qiu , JingWen Jia , Akira Matsumoto , Terumasa Kato , Zhe Wang , Yan Liu , Keiji Maruoka
{"title":"Photoinduced radical CH alkylation by sulfoxonium, sulfonium, selenium and pyridinium ylides as new HAT organocatalysts","authors":"Shuwen Chen ,&nbsp;Hui Qiu ,&nbsp;JingWen Jia ,&nbsp;Akira Matsumoto ,&nbsp;Terumasa Kato ,&nbsp;Zhe Wang ,&nbsp;Yan Liu ,&nbsp;Keiji Maruoka","doi":"10.1016/j.tetlet.2025.155590","DOIUrl":"10.1016/j.tetlet.2025.155590","url":null,"abstract":"<div><div>A photoinduced radical C<img>H alkylation reaction using sulfoxonium and sulfonium ylides as hydrogen atom transfer (HAT) catalysts has been developed. The reaction of tetrahydrofuran derivatives or aldehydes with phenyl vinyl sulfone in the presence of photoredox catalyst and HAT catalysts with base under blue light irradiation afforded C<img>C coupling products in moderate-to-good yields. This approach was successfully applied using similar selenium and pyridinium ylides as HAT catalysts.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"164 ","pages":"Article 155590"},"PeriodicalIF":1.5,"publicationDate":"2025-05-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143942045","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
Synthetic studies on fusicoccin A: Alternative synthetic approach to the C-ring fragment 丝梭霉素A的合成研究：c环片段的替代合成方法
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-05 DOI: 10.1016/j.tetlet.2025.155631
Rikuto Oshima, Masahisa Nakada
{"title":"Synthetic studies on fusicoccin A: Alternative synthetic approach to the C-ring fragment","authors":"Rikuto Oshima,&nbsp;Masahisa Nakada","doi":"10.1016/j.tetlet.2025.155631","DOIUrl":"10.1016/j.tetlet.2025.155631","url":null,"abstract":"<div><div>An enantioselective synthetic method for the C-ring fragment of fusicoccin A, starting from the CBS reduction, is described. The key steps in this synthesis involve the regioselective formation of <em>p</em>-methoxybenzylidene acetal, the construction of the C15 asymmetric carbon of fusicoccin A by a highly stereoselective Michael reaction, and the regioselective reduction of <em>p</em>-methoxybenzylidene acetal. This synthesis of the C-ring fragment was performed in 16 steps. In contrast, the synthesis starting from the baker's yeast reduction, which was developed simultaneously, involved 11 steps. While the baker's yeast-mediated approach is shorter, the baker's yeast reduction suffers from variable conversion efficiency. Therefore, the synthesis via CBS reduction could be an efficient alternative synthetic method for the C-ring fragment.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"164 ","pages":"Article 155631"},"PeriodicalIF":1.5,"publicationDate":"2025-05-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143942043","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 cycloisomerization of O-tethered 1,6-enynes to phosphinylated 3,6-dihydropyrans 可见光诱导的o系1,6-炔环异构化成膦化3,6-二氢吡喃
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-03 DOI: 10.1016/j.tetlet.2025.155628
Yifan Hu, Silong Chen, Nan Huang, Qian Chen
{"title":"Visible-light-induced cycloisomerization of O-tethered 1,6-enynes to phosphinylated 3,6-dihydropyrans","authors":"Yifan Hu,&nbsp;Silong Chen,&nbsp;Nan Huang,&nbsp;Qian Chen","doi":"10.1016/j.tetlet.2025.155628","DOIUrl":"10.1016/j.tetlet.2025.155628","url":null,"abstract":"<div><div>Phosphorus-substituted heterocycles are core motifs in a large amount of biologically active compounds. In this research, a photocatalytic cycloisomerization of <em>O</em>-tethered 1,6-enynes with diarylphosphine oxides under a visible-light irradiation has been achieved. This method provides rapid and efficient access to phosphinylated heterocycles (27 examples) with good functional group compatibility under mild conditions. Spectroscopic studies suggest that a reductive quenching of the excited photocatalyst Ir(III)* with diarylphosphine oxides generates phosphinyl radicals, which undergo a tandem radical cyclization of <em>O</em>-tethered 1,6-enynes to afford the desired phosphinylated 3,6-dihydropyrans.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"163 ","pages":"Article 155628"},"PeriodicalIF":1.5,"publicationDate":"2025-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143917581","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
Mn(OAc)3 promoted radical cyclization of vinyl isocyanides: Synthesis of isoquinoline-1-sulfonates and derivatives
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-03 DOI: 10.1016/j.tetlet.2025.155629
Xin Gu , Yan Zhang , Ruiming Zhang , Yijie Wang , Shuai Liang , Yongmei Xie
{"title":"Mn(OAc)3 promoted radical cyclization of vinyl isocyanides: Synthesis of isoquinoline-1-sulfonates and derivatives","authors":"Xin Gu ,&nbsp;Yan Zhang ,&nbsp;Ruiming Zhang ,&nbsp;Yijie Wang ,&nbsp;Shuai Liang ,&nbsp;Yongmei Xie","doi":"10.1016/j.tetlet.2025.155629","DOIUrl":"10.1016/j.tetlet.2025.155629","url":null,"abstract":"<div><div>This study presents a Mn(OAc)<sub>3</sub>-promoted radical cyclization of vinyl isocyanides to efficiently synthesize 1-functionalized isoquinolines. Using the Mn(OAc)<sub>3</sub>-K<sub>2</sub>S<sub>2</sub>O<sub>5</sub>-HFIP system, 13 isoquinoline-1-sulfonates were prepared in good yields under mild conditions. These sulfonates were further converted into 1-chloro, 1-methoxy, 1-phenoxy, and 1-amino isoquinolines, demonstrating their potential as versatile intermediates.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"164 ","pages":"Article 155629"},"PeriodicalIF":1.5,"publicationDate":"2025-05-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143942042","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
Erratum to “Investigation and optimization of metal- and organocatalyzed decarboxylative radical addition of carboxylic acids to Seebach-Beckwith dehydroalanine towards optically pure unnatural amino acids” [Tetrahedron Lett. 159 (2025) 155507] 对“对Seebach-Beckwith脱氢丙氨酸的金属和有机催化脱羧自由基加成对光学纯非天然氨基酸的研究和优化”的更正[Tetrahedron Lett] . 159 (2025) 155507]
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-02 DOI: 10.1016/j.tetlet.2025.155616
Ilia Perov, Karizza F. Catenza, Jose Jr Abucay, Yu-Ting Hsiao, John C. Vederas
{"title":"Erratum to “Investigation and optimization of metal- and organocatalyzed decarboxylative radical addition of carboxylic acids to Seebach-Beckwith dehydroalanine towards optically pure unnatural amino acids” [Tetrahedron Lett. 159 (2025) 155507]","authors":"Ilia Perov,&nbsp;Karizza F. Catenza,&nbsp;Jose Jr Abucay,&nbsp;Yu-Ting Hsiao,&nbsp;John C. Vederas","doi":"10.1016/j.tetlet.2025.155616","DOIUrl":"10.1016/j.tetlet.2025.155616","url":null,"abstract":"","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"163 ","pages":"Article 155616"},"PeriodicalIF":1.5,"publicationDate":"2025-05-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143917685","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
An undescribed chromene glucoside from the endophytic Paracylindrocarpon sp. KMU22201 associated with Delphinium yunnanense 从云南飞凤属内生植物Paracylindrocarpon sp. KMU22201中提取的一种未描述的铬糖苷
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-01 DOI: 10.1016/j.tetlet.2025.155632
Wen-Yu Huang , Hong-Tao Li , Wang-Cui Xu, Ya-Ting Shao, Han-Wei Ruan, Jie Guo, Wei Li
{"title":"An undescribed chromene glucoside from the endophytic Paracylindrocarpon sp. KMU22201 associated with Delphinium yunnanense","authors":"Wen-Yu Huang ,&nbsp;Hong-Tao Li ,&nbsp;Wang-Cui Xu,&nbsp;Ya-Ting Shao,&nbsp;Han-Wei Ruan,&nbsp;Jie Guo,&nbsp;Wei Li","doi":"10.1016/j.tetlet.2025.155632","DOIUrl":"10.1016/j.tetlet.2025.155632","url":null,"abstract":"<div><div>In our continuous work on the isolation of endophytes, the fungal strain KMU22201 was obtained from the roots of <em>Delphinium yunnanense</em>. Based on phylogenetic analysis, it was identified as <em>Paracylindrocarpon</em> sp. Despite the potential of this endophytic fungus, to our knowledge, its genetic and metabolic diversity, functional activity, and regulatory interactions with <em>D. yunnanense</em> remain to be explored. Investigation of the secondary metabolites of the endophytic <em>Paracylindrocarpon</em> sp. KMU22201 led to the isolation of one undescribed chromene glucoside, dehydromene (<strong>1</strong>), along with the reported compounds, 2,2-dimethyl-2<em>H</em>-1-benzopyran-6-ol (<strong>2</strong>) and methyl-p-hydroquinone (<strong>3</strong>). The structures were established unambiguously via extensive spectroscopic analysis. According to structural characteristic, a plausible biosynthetic pathway for compounds <strong>1</strong>–<strong>3</strong> was proposed. Bio-evaluations indicated that compound <strong>1</strong> exhibited weak anti-acetylcholinesterase and anti-inflammatory activities.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"165 ","pages":"Article 155632"},"PeriodicalIF":1.5,"publicationDate":"2025-05-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144168533","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
Corrigendum to “A convenient one-pot synthesis of novel benzo[g]benzo[4,5]imidazo[2,1-b]quinazolines through Knoevenagel/Michael/cyclization cascade reaction” [Tetrahedron Letters 137 (2024) 154933] “通过Knoevenagel/Michael/环化级联反应一锅合成新型苯并[g]苯并[4,5]咪唑[2,1-b]喹唑啉”的更正[Tetrahedron Letters] 137 (2024) 154933]
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-30 DOI: 10.1016/j.tetlet.2025.155625
Mohaddeseh Ahmadusefi-Sarhadi, Hossein Mehrabi, Farzaneh Alizadeh-Bami
{"title":"Corrigendum to “A convenient one-pot synthesis of novel benzo[g]benzo[4,5]imidazo[2,1-b]quinazolines through Knoevenagel/Michael/cyclization cascade reaction” [Tetrahedron Letters 137 (2024) 154933]","authors":"Mohaddeseh Ahmadusefi-Sarhadi,&nbsp;Hossein Mehrabi,&nbsp;Farzaneh Alizadeh-Bami","doi":"10.1016/j.tetlet.2025.155625","DOIUrl":"10.1016/j.tetlet.2025.155625","url":null,"abstract":"","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"164 ","pages":"Article 155625"},"PeriodicalIF":1.5,"publicationDate":"2025-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143942046","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
Photocatalytic asymmetric cross-dehydrogenative coupling of tetrahydroisoquinoline scaffolds 四氢异喹啉支架的光催化不对称交叉脱氢偶联
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-30 DOI: 10.1016/j.tetlet.2025.155630
Biplob Borah , L. Raju Chowhan
{"title":"Photocatalytic asymmetric cross-dehydrogenative coupling of tetrahydroisoquinoline scaffolds","authors":"Biplob Borah ,&nbsp;L. Raju Chowhan","doi":"10.1016/j.tetlet.2025.155630","DOIUrl":"10.1016/j.tetlet.2025.155630","url":null,"abstract":"<div><div>Tetrahydroisoquinoline (THIQ) scaffolds represent a significant family of nitrogen-containing heterocyclic compounds encountered in numerous natural alkaloids and drug molecules. Consequently, the development of elegant synthetic strategies for their synthesis and functionalization into value-added compounds, providing dual reactivity and activity, is highly desired but challenging. Recently, the synergistic combination of asymmetric catalysis and visible-light-induced photoredox catalysis for accessing complex molecules of potential therapeutic interest has emerged as a fascinating key area in organic chemistry. In this context, and considering the importance of THIQ derivatives, herein, we aim to demonstrate a summary of the recent progress achieved in the direct cross-dehydrogenative coupling of THIQ scaffolds by employing combined photoredox and asymmetric catalysis. Besides disclosing the advantages, limitations, and challenges associated with the presented works, their drawbacks and mechanistic rationalizations are also discussed.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"164 ","pages":"Article 155630"},"PeriodicalIF":1.5,"publicationDate":"2025-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143942148","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
Concise synthesis of (±)-gomadalactone A （±）-戈马达拉内酯A的简明合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-29 DOI: 10.1016/j.tetlet.2025.155623
Ryosuke Ashizaki, Ryo Katsuta, Shinnosuke Wakamori, Tomoo Nukada, Ken Ishigami
{"title":"Concise synthesis of (±)-gomadalactone A","authors":"Ryosuke Ashizaki,&nbsp;Ryo Katsuta,&nbsp;Shinnosuke Wakamori,&nbsp;Tomoo Nukada,&nbsp;Ken Ishigami","doi":"10.1016/j.tetlet.2025.155623","DOIUrl":"10.1016/j.tetlet.2025.155623","url":null,"abstract":"<div><div>We report the synthesis of (±)-gomadalactone A, a contact sex pheromone of the white-spotted longicorn beetle (<em>Anoplophora malasiaca</em>). The synthesis employs Vassilikogiannakis' one-pot, photo-driven cyclopentenone synthesis from a furan derivative, followed by lactonization, to efficiently construct a distinctive 3-oxabicyclo[3.3.0]octane framework. This eleven-step process starts from methyl 2-furylacetate, produced (±)-gomadalactone A in an overall yield of 1 %.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"163 ","pages":"Article 155623"},"PeriodicalIF":1.5,"publicationDate":"2025-04-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143917580","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
A concise formal synthesis of bufogargarizin B bufogargarizin B的简洁形式化合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-04-28 DOI: 10.1016/j.tetlet.2025.155627
Yuxin Xie, Huiling Yang, Yuxuan Tang, Jie Zhao, Hailian Li, Liang Xu
{"title":"A concise formal synthesis of bufogargarizin B","authors":"Yuxin Xie,&nbsp;Huiling Yang,&nbsp;Yuxuan Tang,&nbsp;Jie Zhao,&nbsp;Hailian Li,&nbsp;Liang Xu","doi":"10.1016/j.tetlet.2025.155627","DOIUrl":"10.1016/j.tetlet.2025.155627","url":null,"abstract":"<div><div>A concise and scalable formal synthesis of bufogargarizin B has been achieved by completing the synthesis of the advanced [5–7–6–5] tetracyclic intermediate <strong>II</strong> in 8 steps with 36 % overall yield from commercially available estrone <strong>8</strong>. Key features of the synthesis include stereoselective reduction of the carbonyl group and an oxidative cleavage/transannular aldol cascade reaction to rapidly construct the rearranged A/B ring system and three stereogenic centers. This study presents a new synthetic approach to the unique rearranged framework of bufogargarizin B and related steroids.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"164 ","pages":"Article 155627"},"PeriodicalIF":1.5,"publicationDate":"2025-04-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143942041","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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