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Diversity-Oriented Synthesis of Spirocyclopentadiene Oxindoles and 2-Acyl Cyclopenta[b]indoles via Intramolecular Wittig Reaction. 分子内Wittig反应合成螺旋环戊二烯吲哚和2-酰基环戊[b]吲哚
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-10-03 DOI: 10.1021/acs.orglett.5c03242
Yu-Hsuan Chen,Ru-Yin Yu,Wey-Chyng Jeng,Chen-Ling Chang,Jhih-Syuan Wu,Digambar Abasaheb Nevrekar,Raghunath Maruti Walunj,Yi-Ru Chen,Gangababu Marri,Wenwei Lin
{"title":"Diversity-Oriented Synthesis of Spirocyclopentadiene Oxindoles and 2-Acyl Cyclopenta[b]indoles via Intramolecular Wittig Reaction.","authors":"Yu-Hsuan Chen,Ru-Yin Yu,Wey-Chyng Jeng,Chen-Ling Chang,Jhih-Syuan Wu,Digambar Abasaheb Nevrekar,Raghunath Maruti Walunj,Yi-Ru Chen,Gangababu Marri,Wenwei Lin","doi":"10.1021/acs.orglett.5c03242","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03242","url":null,"abstract":"Herein, we report an efficient strategy for the diversity-oriented synthesis of spirocyclopentadiene oxindoles and 2-acyl cyclopenta[b]indoles. A phospha-1,6-addition of PBu3 to α,β,γ,δ-unsaturated oxindoles provides phosphorus zwitterions as key intermediates and a branching point for the synthesis of these diverse cyclic products. Notably, spiro compounds are formed via a unique δ-C-acylation/Wittig reaction sequence, while the proton transfer/Wittig/β-acylation reactions afforded 2-acyl cyclopenta[b]indoles. Significantly, this study discloses the first report of a direct β-acylation reaction of an α,β-unsaturated ester bearing an endocyclic double bond.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"28 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145209346","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Indopexines A and B: Two Prenylated Isoindoline Alkaloids from the Fungus Aspergillus sp. TJ507. 吲哚内酯A和B：两种来自真菌曲霉sp. TJ507的异吲哚生物碱。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-10-03 DOI: 10.1021/acs.orglett.5c03829
Yeting Zhang,Qing Li,Zhengyi Shi,Xueqi Lan,Jinlong Zhang,Ming Chen,Xinye Huang,Kuansong Wang,Changxing Qi,Yonghui Zhang
{"title":"Indopexines A and B: Two Prenylated Isoindoline Alkaloids from the Fungus Aspergillus sp. TJ507.","authors":"Yeting Zhang,Qing Li,Zhengyi Shi,Xueqi Lan,Jinlong Zhang,Ming Chen,Xinye Huang,Kuansong Wang,Changxing Qi,Yonghui Zhang","doi":"10.1021/acs.orglett.5c03829","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03829","url":null,"abstract":"Indopexines A (1) and B (2), two prenylated isoindoline alkaloids, were isolated from Aspergillus sp. TJ507. Their structures were determined by extensive spectroscopic analysis, CASE algorithms, quantum 1H and 13C NMR DP4+, and electronic circular dichroism calculations. Structurally, 1 was the first examples of isoindoline alkaloids bearing a 6/5/5/6 ring based on the 2-oxa-10-azatetracyclo-[7.7.0.01,12.03,8]cetane core, while 2 featured an 5,20-bioxa-1-azapencyclo-[10.7.1.01,12.06,11.013,18]lcosane moiety. Furthermore, 1 displayed an inhibitory effect toward triple-negative breast cancer cells through the Rap1/PI3K/AKT signaling pathway.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"44 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145209348","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 Dibenzo[a,c]phenazines through Brønsted Acid-Catalyzed Skeletal Editing of 2-Arylindoles with 1,2-Diaminoarenes. Brønsted酸催化1,2-二氨基芳烃骨架编辑合成二苯并[a，c]非那嗪类化合物。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-10-03 DOI: 10.1021/acs.orglett.5c03703
Kun Li,Hai-Fang Lin,Hong-Yan Bi,Wei-Min Shi,Xiao-Pan Ma,Dong-Liang Mo
{"title":"Synthesis of Dibenzo[a,c]phenazines through Brønsted Acid-Catalyzed Skeletal Editing of 2-Arylindoles with 1,2-Diaminoarenes.","authors":"Kun Li,Hai-Fang Lin,Hong-Yan Bi,Wei-Min Shi,Xiao-Pan Ma,Dong-Liang Mo","doi":"10.1021/acs.orglett.5c03703","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03703","url":null,"abstract":"Herein, Brønsted acid-catalyzed skeletal editing of 2-arylindoles with 1,2-diaminoarenes in the presence of tert-butyl nitrite (TBN) has been developed to prepare various dibenzo[a,c]phenazines in moderate to good yields. Mechanistic studies revealed that this skeletal editing of indoles involved a sequence of nitrosation, condensation, cyclization, diazotization, and intramolecular electrophilic substitution over five steps in one pot. More importantly, the dibenzo[a,c]phenazine could be easily obtained on a gram scale and novel π-extended polyaromatic dibenzo[a,c]phenazine derivatives were obtained by further transformations that show the fluorescence emission wavelength in near-infrared region I (NIR-I). This example represents the first skeletal editing of indoles through a ring-opening and denitrogenation strategy.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"10 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-10-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145209042","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Harnessing gem-Diboron Radicals: A Ni-Catalyzed Reductive Coupling Platform for Diverse sp3-Rich Molecular Architectures. 利用宝石-二硼自由基：ni催化的多种sp3-富分子结构的还原偶联平台。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-10-02 DOI: 10.1021/acs.orglett.5c03291
Zhen-Qi Wang,Yan-Jie Yang,Xing-Bang Liu,Siyu Wan,Pin Gao,Yuan Huang
{"title":"Harnessing gem-Diboron Radicals: A Ni-Catalyzed Reductive Coupling Platform for Diverse sp3-Rich Molecular Architectures.","authors":"Zhen-Qi Wang,Yan-Jie Yang,Xing-Bang Liu,Siyu Wan,Pin Gao,Yuan Huang","doi":"10.1021/acs.orglett.5c03291","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03291","url":null,"abstract":"Herein, we report a practical nickel-catalyzed reductive cross-coupling of α-chloro-gem-diboron compounds with carbon electrophiles, providing efficient access to a broad range of gem-diboron structures, including previously underdeveloped α-arylated derivatives. This transformation proceeds via an underdeveloped gem-diboron radical intermediate pathway and features mild conditions, operational simplicity, excellent regioselectivity, and broad functional group tolerance. Notably, this method overcomes the long-standing challenge of Csp3-Csp3 bond formation using simple alkyl halide electrophiles, thereby expanding access to traditionally elusive molecular scaffolds.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"98 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145209048","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Sulfinyl-Imine-Assisted Asymmetric [3,3]-Sigmatropic Rearrangement: Generation of Tertiary and Quaternary Stereocenters. 亚胺辅助不对称[3,3]-异位重排：叔、季立体中心的生成。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-10-02 DOI: 10.1021/acs.orglett.5c03577
Ganesh Karan,Susanta Bhunia,Shubham Snehil,Modhu Sudan Maji
{"title":"Sulfinyl-Imine-Assisted Asymmetric [3,3]-Sigmatropic Rearrangement: Generation of Tertiary and Quaternary Stereocenters.","authors":"Ganesh Karan,Susanta Bhunia,Shubham Snehil,Modhu Sudan Maji","doi":"10.1021/acs.orglett.5c03577","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03577","url":null,"abstract":"An asymmetric chemoselective allylation followed by an oxy-Cope rearrangement sequence is developed to efficiently synthesize chiral β-allylated ketoimines bearing quaternary stereocenters in excellent yields and diastereoselectivities. Besides acting as a nucleophile, allylboronic acid also plays the vital role of a Lewis acid promoter, eliminating the need for adding any external catalyst. Applicability of this method was demonstrated by the total syntheses of flustramine alkaloids.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"76 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145203799","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Palladium-Catalyzed Glycosylation for the Highly Stereoselective de Novo Construction of Trideoxy Glycan Motifs from Pyridapeptides B-E. 钯催化糖基化以高立体选择性地从吡啶肽B-E中重新构建三脱氧聚糖基序。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-10-02 DOI: 10.1021/acs.orglett.5c03679
Rui Su,Guozhi Xiao
{"title":"Palladium-Catalyzed Glycosylation for the Highly Stereoselective de Novo Construction of Trideoxy Glycan Motifs from Pyridapeptides B-E.","authors":"Rui Su,Guozhi Xiao","doi":"10.1021/acs.orglett.5c03679","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03679","url":null,"abstract":"Highly stereocontrolled synthesis of tetrasaccharides with 2,3,6-trideoxy rhodinose and amicetose motifs from pyridapeptides D and E has been achieved for the first time. A trideoxy monosaccharide in pyridapeptide B and trideoxy disaccharide in pyridapeptide C were also prepared for structure-activity relationship studies. Synthetic routes feature the following steps: 1) de novo synthesis of glycosyl ester through RhIII-catalyzed asymmetric transfer hydrogenation, Achmatowicz rearrangement, and (S)-BTM-catalyzed acylation; 2) palladium-catalyzed glycosylation for construction of all trideoxyglycosidic linkages; 3) chiral catalyst-controlled tandem reductions of enones.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"120 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145209046","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 Sulfondiimidoates by Desoxychlorination of Sulfonimidamides. 磺胺酰亚胺脱氧氯化法合成磺酰二酰亚胺酯。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-10-02 DOI: 10.1021/acs.orglett.5c03831
Erik Friedrich,Philip Freund,Christian Lorenz,Timo Heinrich,Dorian Didier,Michael Reggelin
{"title":"Synthesis of Sulfondiimidoates by Desoxychlorination of Sulfonimidamides.","authors":"Erik Friedrich,Philip Freund,Christian Lorenz,Timo Heinrich,Dorian Didier,Michael Reggelin","doi":"10.1021/acs.orglett.5c03831","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03831","url":null,"abstract":"A synthetic procedure toward sulfondiimidoates, the aza-oxo inverse sulfonamides, was developed. The sulfondiimidoates reported here were synthesized by desoxychlorination of sulfonimidamides. The in situ generated sulfondiimidoyl chlorides were transformed into the desired sulfondiimidoates by alcoholysis. The method presented allows for redox-neutral access to sulfondiimidoates.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"19 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145209349","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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 Ring-Opening/1,3-Peroxyesterification of Arylcyclopropanes with Carboxylic Acids and tert-Butyl Hydroperoxide. 芳基环丙烷与羧酸和过氧化叔丁基的开环/1,3-过氧酯化反应。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-10-02 DOI: 10.1021/acs.orglett.5c03747
Jun Pan,Shujun Chen,Leiyang Lv,Zhiping Li
{"title":"Photocatalytic Ring-Opening/1,3-Peroxyesterification of Arylcyclopropanes with Carboxylic Acids and tert-Butyl Hydroperoxide.","authors":"Jun Pan,Shujun Chen,Leiyang Lv,Zhiping Li","doi":"10.1021/acs.orglett.5c03747","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03747","url":null,"abstract":"Organic peroxides constitute a privileged family of O-O-containing compounds that serve as indispensable reagents or synthetic intermediates in industrial processes, pharmaceutical manufacturing, and polymer sciences. Herein, we disclose a photocatalytic ring-opening transformation of arylcyclopropanes with carboxylic acids and tert-butyl hydroperoxide, which enables the facile construction of structurally diverse 1,3-peroxyesterification products. This protocol proceeds under exceptionally mild, metal-free conditions with exquisite site-selectivity and broad functional-group tolerance. Besides, late-stage functionalization of bioactive molecules and downstream transformations are also performed.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"25 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145203858","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
Energy-Transfer Excitation of Dibenzothiophene S-Oxide Induces Oxomethylation of Styrenes. 二苯并噻吩s -氧化物的能量转移激发诱导苯乙烯的氧甲基化。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-10-02 DOI: 10.1021/acs.orglett.5c03852
Saki Maejima,Ban Kinoshita,Ryota Wakabayashi,Manabu Abe,Hideki Yorimitsu
{"title":"Energy-Transfer Excitation of Dibenzothiophene S-Oxide Induces Oxomethylation of Styrenes.","authors":"Saki Maejima,Ban Kinoshita,Ryota Wakabayashi,Manabu Abe,Hideki Yorimitsu","doi":"10.1021/acs.orglett.5c03852","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03852","url":null,"abstract":"The photoexcitation of sulfoxides has traditionally required intense UV light irradiation, thereby limiting their applicability in organic synthesis. Here we report that photosensitization under fac-Ir(ppy)3 catalysis and blue-light irradiation effectively excites dibenzothiophene S-oxide under much milder conditions. The excited sulfoxide reacts with DMSO solvent to promote the oxomethylation of styrenes. Mechanistic investigations disclosed that the excited dibenzothiophene S-oxide undergoes rapid fragmentation in DMSO to generate a methyl radical, a methylsulfonyl radical, and dibenzothiophene. This process provides a new photocatalytic method to generate a methyl radical without recourse to peroxides or metal oxidants.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"53 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145209043","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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
cis and trans Forms of Near-Infrared Diazaborepin Frameworks with Two Tetracoordinate Boron Atoms. 含两个四配位硼原子的近红外重氮大麻素骨架的顺式和反式。
IF 5.2 1区 化学
Organic Letters Pub Date : 2025-10-02 DOI: 10.1021/acs.orglett.5c03578
Lingjuan Chen,Jiaqi Dong,Xueguang Liu,Cheng Tao,Deng-Tao Yang
{"title":"cis and trans Forms of Near-Infrared Diazaborepin Frameworks with Two Tetracoordinate Boron Atoms.","authors":"Lingjuan Chen,Jiaqi Dong,Xueguang Liu,Cheng Tao,Deng-Tao Yang","doi":"10.1021/acs.orglett.5c03578","DOIUrl":"https://doi.org/10.1021/acs.orglett.5c03578","url":null,"abstract":"π-Conjugated frameworks cis-BN2h with two diazaborepin moieties and trans-BN2h1 with only one diazaborepin moiety were synthesized via borylation followed by the Scholl reaction. The cis and trans configurations of the substituent on two tetracoordinate boron atoms were controlled by adjusting the reaction solvent, temperature, and concentration. Both molecules exhibit broad absorption across the visible-near-infrared region up to 722 nm. The diazaborepin core is found to enhance electron delocalization and σ-π hyperconjugation, which increase the HOMO energy with a smaller optical bandgap.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"10 1","pages":""},"PeriodicalIF":5.2,"publicationDate":"2025-10-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145209051","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":1,"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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