Tetrahedron最新文献_第3页

Asymmetric synthesis of an optically active 1-benzylindane derivative as a selective agonist for estrogen receptor beta

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-02-01 DOI: 10.1016/j.tet.2024.134409

Shigeru Yonekubo, Motoyasu Ozawa, Chiaki Handa

{"title":"Asymmetric synthesis of an optically active 1-benzylindane derivative as a selective agonist for estrogen receptor beta","authors":"Shigeru Yonekubo, Motoyasu Ozawa, Chiaki Handa","doi":"10.1016/j.tet.2024.134409","DOIUrl":"10.1016/j.tet.2024.134409","url":null,"abstract":"<div><div>1-(3-Fluoro-4-hydroxybenzyl)-5-hydroxy-2,3-dihydro-1H-indene-1-carbonitrile rac-1a is a potent and highly selective agonist for estrogen receptor β that shows potential as a therapeutic agent for obesity and depression in postmenopausal women. To assess the more precise pharmacological actions of rac-1a, a stable and large-scale supply of optically active (R)-1a is required. In this study, our objective was to synthesize (R)-1a by developing a rapid and more efficient asymmetric synthetic pathway. The rapid supply of (R)-1a was accomplished by diastereomeric resolution of the easily obtainable racemic precursor 1-(3-fluoro-4-methoxybenzyl)-5-methoxy-2,3-dihydro-1H-indene-1-carboxylic acid rac-3a using a chiral oxazolidinone auxiliary. Despite the need to discard the unwanted enantiomer, this approach enabled stable gram-scale supply of (R)-1a by a short process that minimized purification by column chromatography. Furthermore, by exploring more efficient synthetic methods, we synthesized chiral precursor (R)-3a by asymmetric desymmetrization of 1,3-diol 5, which is an important reaction in asymmetric synthesis.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"171 ","pages":"Article 134409"},"PeriodicalIF":2.1,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143181145","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 novel peptide-based tetracarboxylate ligands for metal organic framework (MOF) systems and applications

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-02-01 DOI: 10.1016/j.tet.2024.134387

Moustafa Hamaad, Rudolf J. Wehmschulte

引用次数: 0

Cyclohexane-1,3-dione derivatives: Versatile precursors for total synthesis of natural products 环己烷-1,3-二酮衍生物：天然产品全合成的多功能前体

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-02-01 DOI: 10.1016/j.tet.2024.134395

Dharminder Sharma , Manish Kumar , Sandeep Kumar , Megha Mehta , Pralay Das

引用次数: 0

Total synthesis of four natural trans-stilbene O-glucosides

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-02-01 DOI: 10.1016/j.tet.2024.134417

Haiping Qiu, Zongjun Tang, Wenjin Ma, Jiayao Yuan, Wenling Li

引用次数: 0

Diastereodivergent strategy to cis or trans-2-phenyl-3-amino/hydroxypiperidine for the total syntheses of (−)-epi-CP-99,994, (+)-CP-99,994 and (+)-L-733,060

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-02-01 DOI: 10.1016/j.tet.2024.134401

Rodrigo Chico-Merino , Hugo Pilotzi , Vladimir Carranza , María L. Orea , Alan Carrasco-Carballo , Sylvain Bernès , David M. Aparicio , Joel L. Terán

引用次数: 0

Emerging Trends in Manganese Catalyst for C–H Activation

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-02-01 DOI: 10.1016/j.tet.2024.134416

Ritika Sharma, Shiva Pandey, Mohit Mohit, Diwan S. Rawat

引用次数: 0

Synthesis of N-Aroyl methylsulfonyl-substituted phenylalanine esters via enzyme-catalyzed dynamic kinetic resolution of azlactones

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-02-01 DOI: 10.1016/j.tet.2024.134413

Peng Wang, Chunzhi Ju, Lingkai Kong, Jisheng Cai, Guangliang Zhang, Suoqin Zhang

引用次数: 0

Efficient synthesis and properties of bis-benzothiophene[b]-fused BODIPY dyes via Pd(PPh3)2Cl2-catalyzed regioselective cyclization

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-02-01 DOI: 10.1016/j.tet.2024.134427

Jie Li , Yongli Zhang , Juan Xu , Wen Jiang , Zhehui Weng , Xiangguang Li , Yanhua Yang , Shulin Gao

{"title":"Efficient synthesis and properties of bis-benzothiophene[b]-fused BODIPY dyes via Pd(PPh3)2Cl2-catalyzed regioselective cyclization","authors":"Jie Li , Yongli Zhang , Juan Xu , Wen Jiang , Zhehui Weng , Xiangguang Li , Yanhua Yang , Shulin Gao","doi":"10.1016/j.tet.2024.134427","DOIUrl":"10.1016/j.tet.2024.134427","url":null,"abstract":"<div><div>A new method for synthesizing bis-benzothiophene[b]-fused BODIPYs has been developed, enabling the regioselective catalytic cyclization of tetrahalogenated BODIPY, yielding three new near-infrared (NIR) fluorescent dyes, BBTB-1, BBTB-2 and BBTB-3, with high yields (70–77 %) using Pd(PPh3)2Cl2 as a catalyst. This advancement not only enhances synthesis efficiency but also opens new possibilities for designing BODIPY dyes with finely tuned optoelectronic properties. X-ray crystal structure exhibited their excellent planar π-conjugation. Compared to BBTB-3 with electron-donating groups, photophysical and electrochemical analyses of these bis-benzothiophene[b]-fused BODIPYs with electron-withdrawing groups at the meso-position (BBTB-1 and BBTB-2) demonstrated red-shift in both absorption and fluorescence spectra, and a reduction in LUMO energy level and a narrowed HOMO-LUMO gap. Notably, the LUMO energy level of BBTB-1, BBTB-2 were reduced to −3.81 and −3.83 eV, respectively. The exceptional properties of these bis-benzothiophene[b]-fused BODIPYs are expected to broaden their potential application, particularly in organic semiconductor materials, where such optoelectronic characteristics are crucial for enhancing performance.</div></div>","PeriodicalId":437,"journal":{"name":"Tetrahedron","volume":"171 ","pages":"Article 134427"},"PeriodicalIF":2.1,"publicationDate":"2025-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143181115","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

Transition metal-free approach to the direct C–H selenocyanation of 2-iminothiazolines via in situ generated triselenodicyanide

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-02-01 DOI: 10.1016/j.tet.2024.134434

Umang Pithadiya , Jignesh Mehariya , Vaibhav D. Prajapati , Ronak V. Prajapati , Vishal B. Purohit , Vicky Jain , Sharad C. Karad

引用次数: 0

TBAT-catalyzed dioxasilinane formation from beta-hydroxy ketones tbat催化β -羟基酮生成二恶硅烷。

IF 2.1 3区化学

Tetrahedron Pub Date : 2025-02-01 DOI: 10.1016/j.tet.2024.134418

H.J. Peterson, G.W. O'Neil

引用次数: 0