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Studies toward the synthesis of strasseriolide A & B via a ring-closing metathesis strategy 闭环复合策略合成strasseriolide A和B的研究
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-29 DOI: 10.1016/j.tetlet.2025.155669
Bashweshawar S. Dhulshette , Shikha Mittal , Subhash Ghosh
{"title":"Studies toward the synthesis of strasseriolide A & B via a ring-closing metathesis strategy","authors":"Bashweshawar S. Dhulshette ,&nbsp;Shikha Mittal ,&nbsp;Subhash Ghosh","doi":"10.1016/j.tetlet.2025.155669","DOIUrl":"10.1016/j.tetlet.2025.155669","url":null,"abstract":"<div><div>This communication describes a synthetic approach for strasseriolide A &amp; B via ring-closing metathesis reaction. The stereoselective synthesis of key olefin fragments, followed by their assembly, yielded the crucial bis-olefinic intermediate. However, despite our best efforts, the critical ring-closing metathesis reaction was unsuccessful.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155669"},"PeriodicalIF":1.5,"publicationDate":"2025-05-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144184984","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
Iron-catalyzed Glycal cis-Aminoacyloxylation for 2-amino saccharide synthesis 铁催化糖基顺式氨基酰基化合成2-氨基糖
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-28 DOI: 10.1016/j.tetlet.2025.155678
Le Yin , Dakang Zhang , Zixiang Jiang, Pinzhi Wang, Joseph C. Levine, Dylan L. Labbe, Hao Xu
{"title":"Iron-catalyzed Glycal cis-Aminoacyloxylation for 2-amino saccharide synthesis","authors":"Le Yin ,&nbsp;Dakang Zhang ,&nbsp;Zixiang Jiang,&nbsp;Pinzhi Wang,&nbsp;Joseph C. Levine,&nbsp;Dylan L. Labbe,&nbsp;Hao Xu","doi":"10.1016/j.tetlet.2025.155678","DOIUrl":"10.1016/j.tetlet.2025.155678","url":null,"abstract":"<div><div>We report here a new catalytic and exclusively 1,2-<em>cis</em>-selective glycal aminoacyloxylation method for 2-amino saccharide synthesis. This iron-catalyzed glycosylation is effective for a wide variety of glycosyl donors with consistently high stereoselectivity and excellent functional-group compatibility, which facilitates late-stage amino group incorporation for complex-carbohydrate synthesis.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155678"},"PeriodicalIF":1.5,"publicationDate":"2025-05-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144190299","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
Photoredox catalysis enabled selective CN bond cleavage in ring-strained tertiary amines 光氧化还原催化使环应变叔胺的CN键选择性裂解
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-23 DOI: 10.1016/j.tetlet.2025.155666
Yu Zhou, Pu-Sheng Wang
{"title":"Photoredox catalysis enabled selective CN bond cleavage in ring-strained tertiary amines","authors":"Yu Zhou,&nbsp;Pu-Sheng Wang","doi":"10.1016/j.tetlet.2025.155666","DOIUrl":"10.1016/j.tetlet.2025.155666","url":null,"abstract":"<div><div>The selective cleavage of C<img>N bonds in tertiary amines to form secondary amines is a promising strategy for constructing diverse nitrogen-containing compounds. Herein, we introduce a simple method for the selective <em>N</em>-dealkylation of ring-strained tertiary amines under blue LED light irradiation using 4CzIPN as photocatalyst and CCl<sub>4</sub> as oxidant with up to 99% yield.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155666"},"PeriodicalIF":1.5,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144154496","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
Lipase-catalyzed allyloxycarbonylation of alcohols using allyl phenyl carbonate 脂肪酶催化碳酸烯丙基苯醇烯丙氧羰基化反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-23 DOI: 10.1016/j.tetlet.2025.155665
Yuto Yamamoto , Yuki Hatayama , Hideo Kojima
{"title":"Lipase-catalyzed allyloxycarbonylation of alcohols using allyl phenyl carbonate","authors":"Yuto Yamamoto ,&nbsp;Yuki Hatayama ,&nbsp;Hideo Kojima","doi":"10.1016/j.tetlet.2025.155665","DOIUrl":"10.1016/j.tetlet.2025.155665","url":null,"abstract":"<div><div>Lipase-catalyzed allyloxycarbonylation of alcohols using allyl phenyl carbonate was investigated for various primary alcohols. Lipases from <em>Burkholderia cepacia</em>, <em>Pseudomonas fluorescens</em>, and <em>Candida rugosa</em> were found to be effective catalysts. Moderate to good isolated yields (54 %–89 %) were obtained by reaction with allyl phenyl carbonate (0.5–2 equiv.) at 40 °C for 24 h in hexane when a ratio of five times the weight of <em>Candida rugosa</em> lipase to alcohols (0.1 mmol) was used. For the secondary alcohol, 1-phenylethanol, high stereoselectivity was observed when employing <em>Burkholderia cepacia</em> lipase and <em>Pseudomonas fluorescens</em> lipase. This study developed a green, facile methodology for performing allyloxycarbonylation of alcohols using allyl phenyl carbonate as an alternative to allyl chloroformate, which requires cautious handling.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155665"},"PeriodicalIF":1.5,"publicationDate":"2025-05-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144169396","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
Cu(OTf)2 and a novel axially chiral quinoline-arylphenol ligand partner enabled an enantioselective CH functionalization of indoles with vinylogous migratory carbene insertion of α-arylidene diazosuccinimides for stout preparation of chiral maleimides Cu(OTf)2和一种新的轴向手性喹啉-芳基酚配体伙伴使吲哚的对映选择性CH功能化与α-芳基重氮琥珀酰亚胺的vinyous迁移碳插入，以制备手性马来酰亚胺
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-22 DOI: 10.1016/j.tetlet.2025.155662
Chun-Jun Zhu , Qian-Mao Zhang , Hao Fan , Xiao Fu , Chun-Chun Tang , Wen-Juan Wan , Fang Tian , Li-Xin Wang
{"title":"Cu(OTf)2 and a novel axially chiral quinoline-arylphenol ligand partner enabled an enantioselective CH functionalization of indoles with vinylogous migratory carbene insertion of α-arylidene diazosuccinimides for stout preparation of chiral maleimides","authors":"Chun-Jun Zhu ,&nbsp;Qian-Mao Zhang ,&nbsp;Hao Fan ,&nbsp;Xiao Fu ,&nbsp;Chun-Chun Tang ,&nbsp;Wen-Juan Wan ,&nbsp;Fang Tian ,&nbsp;Li-Xin Wang","doi":"10.1016/j.tetlet.2025.155662","DOIUrl":"10.1016/j.tetlet.2025.155662","url":null,"abstract":"<div><div>An enantioselective vinylogous migratory carbene insertion for C<img>H functionalization of indoles with α-arylidene diazo-succinimides has been disclosed in the presence of catalytic novel axially chiral quinoline-naphthanol ligand <strong>L1</strong> and Cu(OTf)₂ partner. A wide range of chiral maleimides integrated with an indole scaffold were successfully obtained in moderate to good enantioselectivities (up to 91:9 er) with good to excellent yields (up to 91 %) after vinylogous isomerization, which represents a rare example of copper catalyzed enantioselective carbene migratory insertion reaction. Our protocol enables the effective construction of multifunctional chiral indole framework combined with a maleimide moiety, which are widely used as privileged pharmaceutical scaffolds while difficultly available by general synthetic means.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155662"},"PeriodicalIF":1.5,"publicationDate":"2025-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144169395","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
Hydroamination of terminal alkynes to imines catalyzed by a phosphorus-nitrogen PN3-pincer Cu(I) complex 磷氮pn3钳形Cu(I)配合物催化末端炔氢胺化制亚胺
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-22 DOI: 10.1016/j.tetlet.2025.155664
Shatha Bin Dawood , Priyanka Chakraborty , Li Yang , Kuo-Wei Huang
{"title":"Hydroamination of terminal alkynes to imines catalyzed by a phosphorus-nitrogen PN3-pincer Cu(I) complex","authors":"Shatha Bin Dawood ,&nbsp;Priyanka Chakraborty ,&nbsp;Li Yang ,&nbsp;Kuo-Wei Huang","doi":"10.1016/j.tetlet.2025.155664","DOIUrl":"10.1016/j.tetlet.2025.155664","url":null,"abstract":"<div><div>Developing catalytic methods that utilize abundant and cost-effective metal complexes to synthesize valuable compounds is a significant focus in organic synthesis. Herein, we describe the synthesis, characterization, and catalytic performance of the bipyridine-based PN<sup>3</sup> pincer Cu(I) complex toward hydroamination of terminal alkynes to prepare imines. This methodology was successfully applied to a variety of alkyne and amine substrates bearing different functional groups to achieve up to 99 % yield of the corresponding imines. A plausible mechanism was derived based on experimental results and literature.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155664"},"PeriodicalIF":1.5,"publicationDate":"2025-05-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144169394","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 β-C(sp2)-H alkylsulfonylation of enamides with phenyliodine(III) dicarboxylates and DABCO-(SO2)2 可见光诱导β-C(sp2)- h烷基磺酰化与苯碘二羧酸和DABCO-(SO2)2
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-21 DOI: 10.1016/j.tetlet.2025.155663
Tiehan Xu , Xi Chen , Xia Zhao , Kui Lu
{"title":"Visible light induced β-C(sp2)-H alkylsulfonylation of enamides with phenyliodine(III) dicarboxylates and DABCO-(SO2)2","authors":"Tiehan Xu ,&nbsp;Xi Chen ,&nbsp;Xia Zhao ,&nbsp;Kui Lu","doi":"10.1016/j.tetlet.2025.155663","DOIUrl":"10.1016/j.tetlet.2025.155663","url":null,"abstract":"<div><div>A convenient and green method for the straightforward synthesis of β-amidovinyl sulfones has been described from enamides, high-valent iodine (III) dicarboxylates and DABCO-(SO<sub>2</sub>)<sub>2</sub> under the irradiation of blue LEDs in the catalysis of 4CzIPN. The mild and metal-free reaction conditions make this protocol as an alternative strategy for the synthesis of β-amidovinyl sulfones.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"167 ","pages":"Article 155663"},"PeriodicalIF":1.5,"publicationDate":"2025-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144154495","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
Electrochemically facilitated synthesis of chlorotoluene 电化学催化合成氯甲苯
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-20 DOI: 10.1016/j.tetlet.2025.155643
Bowen Liu , Yumei Zhu , Xue Qin , Fang Li
{"title":"Electrochemically facilitated synthesis of chlorotoluene","authors":"Bowen Liu ,&nbsp;Yumei Zhu ,&nbsp;Xue Qin ,&nbsp;Fang Li","doi":"10.1016/j.tetlet.2025.155643","DOIUrl":"10.1016/j.tetlet.2025.155643","url":null,"abstract":"<div><div>This research introduces a green and efficient electrochemical method for toluene chlorination using a saturated NaCl solution as the chlorine source and electrolyte. Through systematic optimization of parameters, including electrode materials, electrolysis duration, current intensity, and chlorine sources, a 97.4 % conversion rate was achieved at a current of 500 mA for 6 h. The combination of FeCl₃ and allyl mercaptan significantly enhanced <em>ortho</em>-selectivity (96.4 %). The method is applicable to multiple aromatic hydrocarbons. Compared with traditional methods, it offers notable advantages including efficient, environmentally friendly characteristics and adjustable conditions, which provides useful references for organic synthesis research and potential applications.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"165 ","pages":"Article 155643"},"PeriodicalIF":1.5,"publicationDate":"2025-05-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144106571","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
Asymmetric approach to aromatic bisabolanes via allylic diazene rearrangement (ADR): Total syntheses of (−)-curcumene, (−)-dihydrocurcumene, (−)-nuciferol, and (−)-nuciferal 烯丙基重氮重排（ADR）合成芳香双abolanes的不对称方法：(−)-姜黄烯、(−)-二氢姜黄烯、(−)-nuciferol和(−)- nucifernal的全合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-19 DOI: 10.1016/j.tetlet.2025.155656
Debabrata Mondal , Spoorti B. Patil , Achal Yeola , Vishnumaya Bisai
{"title":"Asymmetric approach to aromatic bisabolanes via allylic diazene rearrangement (ADR): Total syntheses of (−)-curcumene, (−)-dihydrocurcumene, (−)-nuciferol, and (−)-nuciferal","authors":"Debabrata Mondal ,&nbsp;Spoorti B. Patil ,&nbsp;Achal Yeola ,&nbsp;Vishnumaya Bisai","doi":"10.1016/j.tetlet.2025.155656","DOIUrl":"10.1016/j.tetlet.2025.155656","url":null,"abstract":"<div><div>Concise asymmetric approach to the total synthesis of naturally occurring sesquiterpenes have been achieved via a key allylic diazene arrangement (ADR) from a naturally occurring bisabolane sesquiterpenoid, 6-hydroxy-2-methyl-5-(5’-hydroxy-1’(R),5’-dimethyl-hex-3’-enyl)-phenol (<strong>4</strong>) isolated from the resins of <em>Commiphora kuaa</em> (Burseraceae). The ADR goes through a Mitsunobu reaction with <em>o</em>-nitro benzene sulfonyl hydrazide followed by the decomposition of sulfonyl hydrazide adduct following a [3,3]-sigmatropic rearrangement via the extrusion of <em>o</em>-nitro benzene sulfinic acid and nitrogen gas. This strategy has been utilized for an efficient colelctive total synthesis of naturally occurring sesquiterpenoids, (−)-curcumene (<strong>1a</strong>), (−)-dihydrocurcumene (<strong>1b</strong>), (−)-nuciferol (<strong>1c</strong>) and (−)-nuciferal (<strong>1d</strong>).</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"165 ","pages":"Article 155656"},"PeriodicalIF":1.5,"publicationDate":"2025-05-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144090636","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 of tetra-substituted Furfuryl alcohols by Cu/Rh relay catalysis Cu/Rh接力催化合成四取代糠醇
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-05-17 DOI: 10.1016/j.tetlet.2025.155661
Qinglong Liu , Chen Qu , Yubin Zheng , Wangze Song
{"title":"Synthesis of tetra-substituted Furfuryl alcohols by Cu/Rh relay catalysis","authors":"Qinglong Liu ,&nbsp;Chen Qu ,&nbsp;Yubin Zheng ,&nbsp;Wangze Song","doi":"10.1016/j.tetlet.2025.155661","DOIUrl":"10.1016/j.tetlet.2025.155661","url":null,"abstract":"<div><div>It is a challenge to achieve the direct synthesis of tetra-substituted furfuryl alcohols. Herein, we disclosed a one-pot method for the preparation of tetra-substituted furfuryl alcohols with 1,3-dicarbonyl compounds and propargyl esters by Cu/Rh relay catalysis using pyridine-N-oxide as the oxygen source. One C<img>C bond and two C<img>O bonds could be efficiently formed by this approach with mild reaction conditions, which provides a practical approach to access tetra-substituted furfuryl alcohols.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"165 ","pages":"Article 155661"},"PeriodicalIF":1.5,"publicationDate":"2025-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144090637","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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