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A recyclable helical l-Valine-polymer catalyst for highly enantioselective Aldol and oxa-Michael-Aldol cascade reactions 用于高对映选择性Aldol和oxa-Michael-Aldol级联反应的可回收螺旋l-缬氨酸聚合物催化剂
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-10 DOI: 10.1016/j.tet.2025.134775
Zixuan Wang , Chaoxing Chen , Shuyi Wang , Chonglong Li
{"title":"A recyclable helical l-Valine-polymer catalyst for highly enantioselective Aldol and oxa-Michael-Aldol cascade reactions","authors":"Zixuan Wang ,&nbsp;Chaoxing Chen ,&nbsp;Shuyi Wang ,&nbsp;Chonglong Li","doi":"10.1016/j.tet.2025.134775","DOIUrl":"10.1016/j.tet.2025.134775","url":null,"abstract":"<div><div>A novel helical polymer (poly-<strong>1</strong><sub>m</sub>) bearing <span>l</span>-Valine pendant was designed and synthesized. The chiral <span>l</span>-Valine polymer catalyst demonstrated excellent catalytic activity and stereoselectivity in the Aldol reaction. The polymer poly-<strong>1</strong><sub>200</sub> catalyzed the Aldol reaction of cyclopentanone and 4-nitrobenzaldehyde in water, achieving an enantiomeric excess (<em>ee</em>) value of up to 97 % and a diastereomeric ratio (<em>dr</em>) of 42/58. Furthermore, the chiral polymer catalyst can be recycled three times in asymmetric Aldol addition reactions without significant loss of catalytic activity. The same catalyst was applied in the asymmetric oxa-Michael-Aldol cascade reaction of cinnamaldehyde and salicylaldehyde, achieving an enantiomeric excess of 87 %.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134775"},"PeriodicalIF":2.1,"publicationDate":"2025-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144291432","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Macrocyclic musks: Trends in development and synthetic strategies 大环麝香：发展趋势及合成策略
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-10 DOI: 10.1016/j.tet.2025.134767
Vijay R. Gadgil , Abhinandan Chopada , Gauri R. Chavarkar , Revati A. Kulkarni , Shreerang V. Joshi
{"title":"Macrocyclic musks: Trends in development and synthetic strategies","authors":"Vijay R. Gadgil ,&nbsp;Abhinandan Chopada ,&nbsp;Gauri R. Chavarkar ,&nbsp;Revati A. Kulkarni ,&nbsp;Shreerang V. Joshi","doi":"10.1016/j.tet.2025.134767","DOIUrl":"10.1016/j.tet.2025.134767","url":null,"abstract":"<div><div>Macrocyclic musks are popular amongst perfumers for their captivating, long-lasting, and mesmerizing aroma. Renowned for their ability to harmonize with almost every olfactory group, these compounds play a crucial role in enhancing fragrance compositions. Over the last 100 years, numerous approaches have been developed to synthesize these precious compounds. This review aims to consolidate these diverse approaches in a single comprehensive manner. It is structured into four parts for clarity and coherence. The first part is a compilation of structures of macrocyclic compounds that have a musk or musk-like odor and are classified according to the ascending ring size. In the second part, we have attempted to cover as many approaches as possible to synthesize macrocyclic musks. These are based on the key reaction used for constructing the macrocyclic ring and do not follow any specific order. However, we have maintained an ascending order for the ring size in each approach so readers can compare the strategies and starting materials used for different ring sizes. The third part is dedicated to other approaches that are difficult to classify and accommodate in any other previous approach. Finally, the fourth section highlights biocatalytic and enzymatic approaches, reflecting the growing interest in sustainable and biologically inspired synthesis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134767"},"PeriodicalIF":2.1,"publicationDate":"2025-06-10","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144312659","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Towards total synthesis of lophotoxin and congeners: Recent progress and transannulation strategy lophotoxin及其同系物的全合成：最新进展和跨环策略
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-09 DOI: 10.1016/j.tet.2025.134776
Xi Wang, Yu Peng, Wei-Dong Z. Li
{"title":"Towards total synthesis of lophotoxin and congeners: Recent progress and transannulation strategy","authors":"Xi Wang,&nbsp;Yu Peng,&nbsp;Wei-Dong Z. Li","doi":"10.1016/j.tet.2025.134776","DOIUrl":"10.1016/j.tet.2025.134776","url":null,"abstract":"<div><div>Lophotoxin is a structurally unique and prominent marine furanocembranolide natural product. Despite numerous attempts since its discovery in 1981, the total synthesis of lophotoxin has not yet been achieved to date. This review summarized synthetic efforts and recent progress since 1984 in the synthesis of the lophotoxin skeleton and its analogues. Moreover, strategic perspectives on a range of transannulation approaches for furanocembranoid synthesis were also highlighted herein.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134776"},"PeriodicalIF":2.1,"publicationDate":"2025-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144263944","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Ureas and their derivatives as ligands in transition metal catalysis 脲及其衍生物在过渡金属催化中的配体作用
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-09 DOI: 10.1016/j.tet.2025.134781
Shauna M. Paradine
{"title":"Ureas and their derivatives as ligands in transition metal catalysis","authors":"Shauna M. Paradine","doi":"10.1016/j.tet.2025.134781","DOIUrl":"10.1016/j.tet.2025.134781","url":null,"abstract":"<div><div>Ureas and related compounds represent a popular class of organocatalysts, exploiting their dual hydrogen bond donor capacity to promote reactions and enable asymmetric catalysis. The use of these compounds as ligands in transition metal catalysis has been considerably less developed, despite their ease of synthesis and versatility as ligands. However, there have been notable developments over the last 15–20 years that demonstrate the viability of ureas and closely related compounds as an attractive ligand platform for transition metal catalysis. This perspective will highlight seminal work using (thio)ureas as ancillary ligands, where they engage in non-covalent interactions with substrates in the secondary coordination sphere of transition metals, and as primary ligands, where they coordinate directly to the metal to promote catalytic reactions.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134781"},"PeriodicalIF":2.1,"publicationDate":"2025-06-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144298004","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Efficient kinetic resolution of racemic α-quaternary carboxylic acids via bromolactonization catalyzed by a BINOL-derived bifunctional sulfide 二醇衍生双官能团硫化物催化溴内酯化反应外消旋α-季羧酸的高效动力学拆分
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-08 DOI: 10.1016/j.tet.2025.134780
Sao Sumida, Ken Okuno, Mina Yamakawa, Seiji Shirakawa
{"title":"Efficient kinetic resolution of racemic α-quaternary carboxylic acids via bromolactonization catalyzed by a BINOL-derived bifunctional sulfide","authors":"Sao Sumida,&nbsp;Ken Okuno,&nbsp;Mina Yamakawa,&nbsp;Seiji Shirakawa","doi":"10.1016/j.tet.2025.134780","DOIUrl":"10.1016/j.tet.2025.134780","url":null,"abstract":"<div><div>The catalytic kinetic resolution of racemic α-chiral carboxylic acids is an effective strategy for accessing optically active α-chiral carboxylic acid derivatives. While efficient catalytic kinetic resolutions of α-tertiary carboxylic acids have been well-established, the development of effective methods for the catalytic kinetic resolution of α-quaternary carboxylic acids bearing an all-carbon quaternary α-stereocenter remains a significant challenge. To accomplish this challenging project, we herein report an efficient kinetic resolution of α-quaternary carboxylic acids via a BINOL-derived chiral bifunctional sulfide-catalyzed bromolactonization, which produces α,γ-bis-quaternary γ-butyrolactones in high stereoselectivity.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134780"},"PeriodicalIF":2.1,"publicationDate":"2025-06-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144255076","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Chemical constituents of a marine-derived fungus Aspergillus sp. HL24 and their cytotoxic activity 海源真菌曲霉HL24的化学成分及其细胞毒活性
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-07 DOI: 10.1016/j.tet.2025.134778
Ninh Thi Ngoc, Le Thi Vien, Tran Thi Hong Hanh, Nguyen Xuan Cuong, Nguyen Hoai Nam, Chau Van Minh
{"title":"Chemical constituents of a marine-derived fungus Aspergillus sp. HL24 and their cytotoxic activity","authors":"Ninh Thi Ngoc,&nbsp;Le Thi Vien,&nbsp;Tran Thi Hong Hanh,&nbsp;Nguyen Xuan Cuong,&nbsp;Nguyen Hoai Nam,&nbsp;Chau Van Minh","doi":"10.1016/j.tet.2025.134778","DOIUrl":"10.1016/j.tet.2025.134778","url":null,"abstract":"<div><div>Three new compounds, aspergienone (<strong>1</strong>), carbonarone A<sub>1</sub> (<strong>2</strong>) and pestalamide B<sub>1</sub> (<strong>3</strong>), along with five known compounds, were obtained from a marine-derived fungus <em>Aspergillus</em> sp. HL24, isolated from an unidentified coral collected in Halong Bay, Vietnam. Their structures were elucidated by extensive analysis of their 1D, 2D NMR and HRMS data as well as quantum chemical calculations. The absolute configurations of <strong>1</strong> and <strong>3</strong> were determined by comparing experimental and calculated ECD spectra and specific optical rotation values. All compounds were tested for cytotoxic activity against human lung (A549), liver (HepG2), and colorectal (HT-29) cancer cell lines. Among the tested compounds, only <strong>8</strong> exhibited cytotoxicity against HT-29 cells, with an IC<sub>50</sub> value of 90.26 ± 7.67 μM. In addition, docking methods were used to study ligand interactions with the two target proteins 4ASD and 2OH4, which belong to VEGFR2. Results aligned with the experimental cytotoxicity data.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134778"},"PeriodicalIF":2.1,"publicationDate":"2025-06-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144243086","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Direct cross-coupling of phosphonium salts with aryl iodides 磷盐与芳基碘化物的直接交叉偶联
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-06 DOI: 10.1016/j.tet.2025.134772
Meiqi Zhu, Jingdi Wang, Guangcai Qu, Benqiang Cui, Changsheng Cao, Yanhui Shi
{"title":"Direct cross-coupling of phosphonium salts with aryl iodides","authors":"Meiqi Zhu,&nbsp;Jingdi Wang,&nbsp;Guangcai Qu,&nbsp;Benqiang Cui,&nbsp;Changsheng Cao,&nbsp;Yanhui Shi","doi":"10.1016/j.tet.2025.134772","DOIUrl":"10.1016/j.tet.2025.134772","url":null,"abstract":"<div><div>The direct cross-coupling reaction of two electrophiles, triphenylmethyl phosphonium triflates and aryl iodides under mild conditions was developed. The reaction was catalyzed by Pd(PPh<sub>3</sub>)<sub>4</sub> in the presence of Ag<sub>2</sub>O, using Cs<sub>2</sub>CO<sub>3</sub> as the base at 45 °C for 8 h, and various biphenyls were synthesized in medium to excellent yields. The method is scalable and tolerance of many functional groups was observed. The direct arylation of commercially available triarylphosphine can be achieved by a two-step one-pot process. The regioselective arylation of differently substituted aryl phosphonium triflates was observed at the side of sterically hindered and electron-deficient aryl group.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134772"},"PeriodicalIF":2.1,"publicationDate":"2025-06-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144243085","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 oxindoles: A versatile building block towards formation of diverse organic frameworks 烷基二烯氧吲哚：形成多种有机框架的通用构建块
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-06-02 DOI: 10.1016/j.tet.2025.134757
Sayan Pramanik , Rajiv Karmakar , Chhanda Mukhopadhyay
{"title":"Alkylidene oxindoles: A versatile building block towards formation of diverse organic frameworks","authors":"Sayan Pramanik ,&nbsp;Rajiv Karmakar ,&nbsp;Chhanda Mukhopadhyay","doi":"10.1016/j.tet.2025.134757","DOIUrl":"10.1016/j.tet.2025.134757","url":null,"abstract":"<div><div>3-Alkylidene-2-oxindoles are highly reactive intermediates in several key organic reactions. In Michael addition, they readily react with nucleophiles to form carbon-carbon bonds. In multicomponent reactions, they enable the efficient assembly of complex polycyclic structures. Their involvement in cycloaddition reactions facilitates the formation of biologically active, fused ring systems. Enantioselective reactions with 3-alkylidene-2-oxindoles provide chiral molecules with high stereochemical control, crucial for drug development. Additionally, they participate in metal- and radical-mediated C–H functionalization, enabling direct modification of C–H bonds for efficient functionalization in complex molecule synthesis. In this review, we discuss about diverse reactions of 3-alkylidene-2-oxindoles (Mainly Michael addition, multicomponent domino reaction, cycloaddition reaction, enantioselective transformations, C–H functionalization reaction drived by transition metal and radical) that may provide as a section of consistent literature for further research.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134757"},"PeriodicalIF":2.1,"publicationDate":"2025-06-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144203282","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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 of optically active indane building blocks using an enzymatic resolution approach 利用酶解方法合成旋光性吲哚基块
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-05-31 DOI: 10.1016/j.tet.2025.134759
Anna L. Banasevych , Olexandr V. Kucher , Bohdan S. Sosunovych , Nadiya K. Nazarenko , Dina V. Shevchenko , Oleg B. Smolii , Bohdan V. Vashchenko
{"title":"Synthesis of optically active indane building blocks using an enzymatic resolution approach","authors":"Anna L. Banasevych ,&nbsp;Olexandr V. Kucher ,&nbsp;Bohdan S. Sosunovych ,&nbsp;Nadiya K. Nazarenko ,&nbsp;Dina V. Shevchenko ,&nbsp;Oleg B. Smolii ,&nbsp;Bohdan V. Vashchenko","doi":"10.1016/j.tet.2025.134759","DOIUrl":"10.1016/j.tet.2025.134759","url":null,"abstract":"<div><div>A highly efficient synthesis of indane building blocks is described. First, enantioenriched diastereomerically pure 2- and 3-substituted methyl indane alcohols were synthesized using an enzymatic resolution reaction with <em>Amano PS</em> (<em>Burkholderia cepacia lipase</em>) and <em>Novozym 435</em> (<em>Candida antarctica lipase B</em>). Then, obtained <em>cis</em>-alcohols were converted into <em>trans</em>-alcohols using the Mitsunobu reaction with <em>para</em>-nitrobenzoic acid. The Mitsunobu reaction with DPPA was used to obtain azides that were reduced to the corresponding target amines without decreasing <em>ee</em> values. This work expands known approaches to synthesizing indane building blocks and provides an efficient protocol for obtaining optically active alcohols and amines.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134759"},"PeriodicalIF":2.1,"publicationDate":"2025-05-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144221538","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Structures of neo-RA-VII and cyclorubipeptide A, new cyclic hexapeptides from Rubia cordifolia 芦花新环六肽新ra - vii和环二肽A的结构
IF 2.1 3区 化学
Tetrahedron Pub Date : 2025-05-29 DOI: 10.1016/j.tet.2025.134747
Asami Mikura, Koki Tani, Erina Sasahira, Shunsuke Nakano, Jun-ichi Kusano, Hiroto Sato, Tomoyo Hasuda, Koichi Takeya, Yukio Hitotsuyanagi
{"title":"Structures of neo-RA-VII and cyclorubipeptide A, new cyclic hexapeptides from Rubia cordifolia","authors":"Asami Mikura,&nbsp;Koki Tani,&nbsp;Erina Sasahira,&nbsp;Shunsuke Nakano,&nbsp;Jun-ichi Kusano,&nbsp;Hiroto Sato,&nbsp;Tomoyo Hasuda,&nbsp;Koichi Takeya,&nbsp;Yukio Hitotsuyanagi","doi":"10.1016/j.tet.2025.134747","DOIUrl":"10.1016/j.tet.2025.134747","url":null,"abstract":"<div><div>A new bicyclic hexapeptide, neo-RA-VII (<strong>3</strong>), incorporating a 12-membered cyclodityrosine structure, and a new cyclic hexapeptide, cyclorubipeptide A (<strong>4</strong>), were isolated from the roots of <em>Rubia cordifolia</em> L. Their structures were elucidated through the interpretation of spectroscopic data. The structure of <strong>3</strong> was confirmed through total synthesis and that of <strong>4</strong> through chemical correlation with <em>O</em>-seco-RA-V (<strong>14</strong>). The cyclodityrosine unit in compound <strong>3</strong> was synthesized via an intramolecular Suzuki–Miyaura cross-coupling reaction of a dipeptide bearing an iodine atom and a boronic acid group on each aryl ring. Peptides <strong>3</strong> and <strong>4</strong> exhibited cytotoxic activity, with IC<sub>50</sub> values of 5.1 and 4.3 μM against HL-60 cells and 17 and 15 μM against HCT-116 cells, respectively.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"184 ","pages":"Article 134747"},"PeriodicalIF":2.1,"publicationDate":"2025-05-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144230595","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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