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Petasis reaction: An expeditious generation of multiple stereogenic centres Petasis反应：快速生成多个立体中心
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-22 DOI: 10.1016/j.tetlet.2025.155548
Ayon Sengupta , Chhanda Mukhopadhyay
{"title":"Petasis reaction: An expeditious generation of multiple stereogenic centres","authors":"Ayon Sengupta ,&nbsp;Chhanda Mukhopadhyay","doi":"10.1016/j.tetlet.2025.155548","DOIUrl":"10.1016/j.tetlet.2025.155548","url":null,"abstract":"<div><div>In view of the versatility of the Petasis reaction (PR) for the synthesis of different organic compounds with enormous applications in biology and pharmaceutics, this short review is intended to focus on the Petasis and associated reactions that produces multiple (more than one) stereogenic centres. The reactions were organised and categorized on the basis of the number of stereocenters centres generated in the overall process. The multicomponent reactions with dual PR sequences, asymmetric PRs, and build/couple/pair (B/C/P) strategies involving PR/IMDA(intramolecular Diels–Alder)/RCM(ring-closing metathesis)/ROM(ring-opening metathesis) cascades were captured in this review.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155548"},"PeriodicalIF":1.5,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143714902","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
Toddamarin A, a rare atropisomeric biscoumarin with multi-axis from Toddalia asiatica 苦豆素A是一种罕见的多轴双香豆素
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-22 DOI: 10.1016/j.tetlet.2025.155556
Shan-Shan Chen , Li Wang , Yi-Nong Wang , Bang-Yin Tan , Chang-Bin Wang , Yu Duan , Yun-Li Zhao , Xiao-Dong Luo
{"title":"Toddamarin A, a rare atropisomeric biscoumarin with multi-axis from Toddalia asiatica","authors":"Shan-Shan Chen ,&nbsp;Li Wang ,&nbsp;Yi-Nong Wang ,&nbsp;Bang-Yin Tan ,&nbsp;Chang-Bin Wang ,&nbsp;Yu Duan ,&nbsp;Yun-Li Zhao ,&nbsp;Xiao-Dong Luo","doi":"10.1016/j.tetlet.2025.155556","DOIUrl":"10.1016/j.tetlet.2025.155556","url":null,"abstract":"<div><div>Toddamarin A, a new prenylated coumarin dimer with a new type of 1,3,4,4,5-pentasubstituted cyclohexene ring was isolated from the roots of <em>Toddalia asiatica</em>. Notably, it possessed both chiral centers and stereogenic axes, exhibiting atropisomeric property as evidenced by ROESY and variable temperature NMR experiment. Additionally, a plausible biosynthetic pathway was proposed. The finding enriched the chemical diversity of coumarins<em>,</em> and provided promising molecular template for stereoselective synthesis.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155556"},"PeriodicalIF":1.5,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143714898","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
Diversification of acridinium photocatalysts: Property tuning and reactivity in model reactions 吖啶光催化剂的多样化：性质调整和模型反应的反应性
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-22 DOI: 10.1016/j.tetlet.2025.155546
Jason Y. Wang , Flora Fan , Madeline E. Ruos , Leticia Adao Gomes , Mimi Lavin , Thomas J. O'Connor , Steven A. Lopez , Abigail G. Doyle
{"title":"Diversification of acridinium photocatalysts: Property tuning and reactivity in model reactions","authors":"Jason Y. Wang ,&nbsp;Flora Fan ,&nbsp;Madeline E. Ruos ,&nbsp;Leticia Adao Gomes ,&nbsp;Mimi Lavin ,&nbsp;Thomas J. O'Connor ,&nbsp;Steven A. Lopez ,&nbsp;Abigail G. Doyle","doi":"10.1016/j.tetlet.2025.155546","DOIUrl":"10.1016/j.tetlet.2025.155546","url":null,"abstract":"<div><div>Herein, we describe the discovery and characterization of multiple <em>N</em>-(hetero)aryl, <em>N</em>-benzyl and <em>N</em>-alkyl derivatives of 9-mesityl-3,6-di-<em>tert</em>-butyl-10-phenyl acridinium photocatalyst. The catalytic performances of these catalysts as photo-oxidant or photo-reductant (via <em>in situ</em> generated acridine radical) were compared in three model reactions. We also identified improved catalytic conditions for a previous cyanoarene-catalyzed nucleophilic amination reaction using a synthesized <em>N</em>-cycloheptyl acridinium catalyst (up to 98 % yield).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155546"},"PeriodicalIF":1.5,"publicationDate":"2025-03-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143682059","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
An organic small molecule fluorescent probe for nondestructive detection of Zn2+ in plants 一种无损检测植物中Zn2+的有机小分子荧光探针
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-21 DOI: 10.1016/j.tetlet.2025.155553
Junyi Zheng , Siyi Li , Shunpeng Bai , Xiao Liu , Ruitao Sun , Shengzhen Xu , Wei Qu
{"title":"An organic small molecule fluorescent probe for nondestructive detection of Zn2+ in plants","authors":"Junyi Zheng ,&nbsp;Siyi Li ,&nbsp;Shunpeng Bai ,&nbsp;Xiao Liu ,&nbsp;Ruitao Sun ,&nbsp;Shengzhen Xu ,&nbsp;Wei Qu","doi":"10.1016/j.tetlet.2025.155553","DOIUrl":"10.1016/j.tetlet.2025.155553","url":null,"abstract":"<div><div>In this study, a novel two-photon fluorescent probe, <strong>ZT1</strong>, leveraging the photoinduced electron transfer (PET) effect was designed and synthesized. The probe employs 4-trifluoromethyl coumarin as the fluorophore and 2,2′-dipicolylamine (DPA) as the Zn<sup>2+</sup> recognition group, enabling non-destructive detection of Zn<sup>2+</sup> in <em>Arabidopsis thaliana</em>. <strong>ZT1</strong> demonstrated exceptional selectivity for Zn<sup>2+</sup> in both <em>in vitro</em> and <em>in vivo</em> assays, maintained stability across a pH range of 6–8, featured a detection limit as low as 13.96 nM, and exhibited a large Stokes shift (177 nm). The probe facilitated high-resolution visualization of Zn<sup>2+</sup> in the root tips and leaf tissues of <em>Arabidopsis thaliana</em> and demonstrated remarkable reversibility in cyclic experiments. This work establishes a robust toolkit that overcomes longstanding limitations in plant metal ion imaging, offering mechanistic insights into zinc-regulated physiological processes.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"161 ","pages":"Article 155553"},"PeriodicalIF":1.5,"publicationDate":"2025-03-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143776698","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 approach to the enantioselective synthesis of (+)-neovibsanins A and B 对映选择性合成(+)-neovibsanins A和B的改进方法
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-21 DOI: 10.1016/j.tetlet.2025.155552
Tomoyuki Esumi , Emi Matsuo , Mitsuki Tanahara , Tadashi Hyodo , Kentaro Yamaguchi , Hirofumi Yamamoto , Yoshinori Asakawa
{"title":"Improved approach to the enantioselective synthesis of (+)-neovibsanins A and B","authors":"Tomoyuki Esumi ,&nbsp;Emi Matsuo ,&nbsp;Mitsuki Tanahara ,&nbsp;Tadashi Hyodo ,&nbsp;Kentaro Yamaguchi ,&nbsp;Hirofumi Yamamoto ,&nbsp;Yoshinori Asakawa","doi":"10.1016/j.tetlet.2025.155552","DOIUrl":"10.1016/j.tetlet.2025.155552","url":null,"abstract":"<div><div>A key intermediate in the enantioselective synthesis of (+)-neovibsanins A and B was synthesized from (<em>E</em>)-geranic acid in only six steps. Strategic asymmetric 1,4-addition and asymmetric aldol reactions were used to construct successive chiral centers adjacent to a chiral tetraalkylated (all‑carbon) quaternary center and ring closing metathesis using Grubbs catalyst, forming the A-ring moiety was effective in reducing the number of steps leading to the key intermediate.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"161 ","pages":"Article 155552"},"PeriodicalIF":1.5,"publicationDate":"2025-03-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143785060","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 convenient ammonium chloride facilitated mild and efficient synthesis of Benzazepinoindole derivatives through a Pictet-Spengler reaction* 简便的氯化铵通过Pictet-Spengler反应温和高效地合成了苯并氮平吲哚衍生物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-19 DOI: 10.1016/j.tetlet.2025.155529
Chibisree Elanchezhian , Diksha Bansal , Pooja Sivaganesan , Gokulprasanth Nataraj , Mrinal Kanti Das , Saikat Chaudhuri
{"title":"A convenient ammonium chloride facilitated mild and efficient synthesis of Benzazepinoindole derivatives through a Pictet-Spengler reaction*","authors":"Chibisree Elanchezhian ,&nbsp;Diksha Bansal ,&nbsp;Pooja Sivaganesan ,&nbsp;Gokulprasanth Nataraj ,&nbsp;Mrinal Kanti Das ,&nbsp;Saikat Chaudhuri","doi":"10.1016/j.tetlet.2025.155529","DOIUrl":"10.1016/j.tetlet.2025.155529","url":null,"abstract":"<div><div>Benzazepinoindoles are a promising class of compounds in the growing field of heterocyclic chemistry due to their intriguing pharmacological properties. The tetrahydro-benzazepinoindole scaffold, in particular, holds great promise as a versatile framework for drug discovery, especially in the development of antiproliferative and anti-inflammatory agents. In present work, we proposed the synthesis of tetrahydro-benzazepinoindoles starting from alkylated indole and benzaldehyde derivatives using NH<sub>4</sub>Cl, and methanol as solvent. This approach is designed to achieve high efficiency and good to excellent yields, while accommodating diverse functional groups to enhance structural diversity. The scalability of this method was demonstrated through successful gram-scale reactions, highlighting its utility in practical applications. The synthesized compounds were characterized using advanced techniques, including <sup>1</sup>H NMR, <sup>13</sup>C NMR, <sup>19</sup>F NMR, DEPT-135, IR and mass spectrometry, confirming their structural integrity. This work provides a streamlined and reliable strategy for the synthesis of tetrahydro-benzazepinoindoles, contributing to advancements in synthetic methodology and paving the way for the development of novel bioactive molecules with significant therapeutic potential.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155529"},"PeriodicalIF":1.5,"publicationDate":"2025-03-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143654773","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 aerobic C-3 thiocyanation of indoles using carbon dots as photoredox catalyst 利用碳点作为光氧化催化剂，在可见光诱导下进行吲哚的有氧 C-3 硫氰化反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-15 DOI: 10.1016/j.tetlet.2025.155545
Pritesh Khobrekar , Sandesh Bugde
{"title":"Visible-light-induced aerobic C-3 thiocyanation of indoles using carbon dots as photoredox catalyst","authors":"Pritesh Khobrekar ,&nbsp;Sandesh Bugde","doi":"10.1016/j.tetlet.2025.155545","DOIUrl":"10.1016/j.tetlet.2025.155545","url":null,"abstract":"<div><div>In this work, we demonstrate the use of rose-bengal derived carbon dots for C-3 thiocyanation of indoles. These carbon dots serve as an non-toxic, biocompatible and environmentally friendly catalysts for the C-3 thiocyanation reaction. To our best knowledge, this is the first report to use rose-bengal derived carbon dots for C-3 thiocyanation of indoles. The yield of the synthesized derivatives of indoles were found to be good to excellent in the range of 33 % to 84 %.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155545"},"PeriodicalIF":1.5,"publicationDate":"2025-03-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143628573","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
AgNO3 catalysed oxidation of aromatic amines in the presence of hydrogen peroxide AgNO3在过氧化氢的存在下催化芳香胺的氧化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-14 DOI: 10.1016/j.tetlet.2025.155511
Vincenzo Marsicano , Antonio Arcadi , Marco Chiarini
{"title":"AgNO3 catalysed oxidation of aromatic amines in the presence of hydrogen peroxide","authors":"Vincenzo Marsicano ,&nbsp;Antonio Arcadi ,&nbsp;Marco Chiarini","doi":"10.1016/j.tetlet.2025.155511","DOIUrl":"10.1016/j.tetlet.2025.155511","url":null,"abstract":"<div><div>An operationally simple complementary oxidative dimerization of anilines to the corresponding azoxy derivatives by means of AgNO<sub>3</sub> catalysis in the presence of H<sub>2</sub>O<sub>2</sub> as the oxidant is described. Unusual activation of C<img>C triple bonds in the presence of AgNO<sub>3</sub>-H<sub>2</sub>O<sub>2</sub> and amines is expected to facilitate advancements in the applications for silver catalysis in organic synthesis.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155511"},"PeriodicalIF":1.5,"publicationDate":"2025-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143682058","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Synthesis and Structural Confirmation of PyHOPO and its Applicability in Racemization Reduction in Solid-Phase Peptide Synthesis PyHOPO的合成、结构证实及其在固相肽合成中外消旋化还原中的应用
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-10 DOI: 10.1016/j.tetlet.2025.155520
Kwazi Masuku , Anamika Sharma , Sikabwe Noki , Sizwe Zamisa , Ayman El-Faham , Beatriz G. de la Torre , Fernando Albericio
{"title":"Synthesis and Structural Confirmation of PyHOPO and its Applicability in Racemization Reduction in Solid-Phase Peptide Synthesis","authors":"Kwazi Masuku ,&nbsp;Anamika Sharma ,&nbsp;Sikabwe Noki ,&nbsp;Sizwe Zamisa ,&nbsp;Ayman El-Faham ,&nbsp;Beatriz G. de la Torre ,&nbsp;Fernando Albericio","doi":"10.1016/j.tetlet.2025.155520","DOIUrl":"10.1016/j.tetlet.2025.155520","url":null,"abstract":"<div><div>In the current work, PyHOPO was synthesized and well characterized by single ray XRD. The crystal structure unambiguously confirmed the presence of a P-O-N bond rather than a P-O-C bond. The conversion of HOPO to PyHOPO elongates the N<img>O bond length thereby changing the electron density distribution, as evidenced by electrostatic mapping. This highlights the phosphorus atom's electron-donating nature toward the HOPO moiety. PyHOPO was used to prepare pentapeptide H-Tyr-Ser-Ser-Phe-Leu-NH<sub>2</sub>. PyHOPO was then evaluated for racemization study. Racemization was studied in the case of Ser, His and Cys upon incorporation in a tripeptide (Gly-X-Phe-NH<sub>2</sub>; where X = Ser, His, Cys). For the study, it was found that there was no racemization in all the three cases when PyHOPO was used as coupling reagent.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155520"},"PeriodicalIF":1.5,"publicationDate":"2025-03-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143576774","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
引用次数: 0
Construction of Amidines via palladium-catalyzed three-component reaction of Arylacetylenes, t-Butylisonitrile and O-benzoyl Hydroxylamines 钯催化芳基乙炔、t-丁基异腈和邻苯甲酰羟胺三组分反应构建酰胺类化合物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-03-06 DOI: 10.1016/j.tetlet.2025.155534
Jianquan Hong, Feng Zheng, Xiaoyu Wang, Mingyu Ma, Yupeng Yang, Lianguang Huo, Shuai Huang, Changge Zheng
{"title":"Construction of Amidines via palladium-catalyzed three-component reaction of Arylacetylenes, t-Butylisonitrile and O-benzoyl Hydroxylamines","authors":"Jianquan Hong,&nbsp;Feng Zheng,&nbsp;Xiaoyu Wang,&nbsp;Mingyu Ma,&nbsp;Yupeng Yang,&nbsp;Lianguang Huo,&nbsp;Shuai Huang,&nbsp;Changge Zheng","doi":"10.1016/j.tetlet.2025.155534","DOIUrl":"10.1016/j.tetlet.2025.155534","url":null,"abstract":"<div><div>A palladium-catalyzed three-component reaction between arylacetylenes, <em>t</em>-butylisonitrile and <em>O</em>-benzoyl hydroxylamines has been developed. This transformation provides an efficient approach to access various alkynylamidine derivatives <em>via</em> tandem C<img>H activation/insertion/amidination procedure.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"160 ","pages":"Article 155534"},"PeriodicalIF":1.5,"publicationDate":"2025-03-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143594025","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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