Pub Date : 2026-01-16DOI: 10.1016/j.tetlet.2026.155973
Tongming Niu , Zhimin Sun , Huijie Zhang , Dexin Fu , Qingbin Liu
A metal-free protocol using methanesulfonic acid as an efficient mediator was successfully developed for the synthesis of N-aryl-substituted pyrrolidines from amides and tetrahydrofuran. Notably, the cyclic ethers were employed in a dual role as both reactants and reaction medium, which enhances their practicality. Systematic optimization revealed remarkable versatility, demonstrating broad substrate scope encompassing both aliphatic and aromatic amide derivatives.
{"title":"Methanesulfonic acid-mediated direct synthesis of N-aryl-substituted pyrrolidines from amides","authors":"Tongming Niu , Zhimin Sun , Huijie Zhang , Dexin Fu , Qingbin Liu","doi":"10.1016/j.tetlet.2026.155973","DOIUrl":"10.1016/j.tetlet.2026.155973","url":null,"abstract":"<div><div>A metal-free protocol using methanesulfonic acid as an efficient mediator was successfully developed for the synthesis of <em>N</em>-aryl-substituted pyrrolidines from amides and tetrahydrofuran. Notably, the cyclic ethers were employed in a dual role as both reactants and reaction medium, which enhances their practicality. Systematic optimization revealed remarkable versatility, demonstrating broad substrate scope encompassing both aliphatic and aromatic amide derivatives.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"177 ","pages":"Article 155973"},"PeriodicalIF":1.5,"publicationDate":"2026-01-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146025487","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}
Pub Date : 2026-01-15DOI: 10.1016/j.tetlet.2026.155960
Surabhi Upadhyay , Smriti Suryavanshi , Ambika Asati , Manorama Singh , Ankita Rai , Vijai K. Rai
Recent advances in the ring-opening and ring-closing transformations of the three-membered aza-heterocycle aziridine have garnered significant attention in heterocyclic chemistry. Due to their highly strained structure, aziridines readily undergo nucleophilic ring-opening reactions, typically involving cleavage of the C–N bond, followed by cyclization or cycloaddition processes. These transformations enable access to a diverse array of four- to seven-membered heterocycles (often containing one to three heteroatoms), many of which possess structural features of biological and medicinal importance. In this context, the past decade (2015–2025) has seen the emergence of numerous simple, efficient, and sustainable strategies for the synthesis, reactivity, and synthetic utility of aziridines. These developments are comprehensively summarized in this review.
{"title":"Ring-opening ring-closing strategy towards construction of aza-heterocycles from aziridines","authors":"Surabhi Upadhyay , Smriti Suryavanshi , Ambika Asati , Manorama Singh , Ankita Rai , Vijai K. Rai","doi":"10.1016/j.tetlet.2026.155960","DOIUrl":"10.1016/j.tetlet.2026.155960","url":null,"abstract":"<div><div>Recent advances in the ring-opening and ring-closing transformations of the three-membered aza-heterocycle aziridine have garnered significant attention in heterocyclic chemistry. Due to their highly strained structure, aziridines readily undergo nucleophilic ring-opening reactions, typically involving cleavage of the C–N bond, followed by cyclization or cycloaddition processes. These transformations enable access to a diverse array of four- to seven-membered heterocycles (often containing one to three heteroatoms), many of which possess structural features of biological and medicinal importance. In this context, the past decade (2015–2025) has seen the emergence of numerous simple, efficient, and sustainable strategies for the synthesis, reactivity, and synthetic utility of aziridines. These developments are comprehensively summarized in this review.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"177 ","pages":"Article 155960"},"PeriodicalIF":1.5,"publicationDate":"2026-01-15","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"146025486","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}
Pub Date : 2026-01-07DOI: 10.1016/j.tetlet.2026.155959
Yichen Li, Lin Pu
A BINOL-pyridine-based chiral unsymmetric dialdehyde was synthesized. This compound in combination with Zn2+ has exhibited highly chemoselective as well as enantioselective fluorescent response toward lysine, an essential amino acid. It was found that this compound undergoes regioselective macrocyclization with l-lysine but generates a more complex mixture with d-lysine. This difference in reactivity should contribute to the observed chemo- and enantioselectivty in the fluorescence response. This molecular probe can be used at 20 times lower concentration than a previously reported analog for lysine recognition. It has also displayed significantly enhanced enantioselectivity over the previously reported analog with the enantioselective fluorescence intensity ratio (ef) increased from 16.9 to 60.0 [ef = (IL-I0)/(ID-I0). I0: the fluorescence intensity of the probe in the absence of the amino acid].
{"title":"Chemoselective and enantioselective fluorescent recognition of lysine by a BINOL-pyridine-based chiral dialdehyde","authors":"Yichen Li, Lin Pu","doi":"10.1016/j.tetlet.2026.155959","DOIUrl":"10.1016/j.tetlet.2026.155959","url":null,"abstract":"<div><div>A BINOL-pyridine-based chiral unsymmetric dialdehyde was synthesized. This compound in combination with Zn<sup>2+</sup> has exhibited highly chemoselective as well as enantioselective fluorescent response toward lysine, an essential amino acid. It was found that this compound undergoes regioselective macrocyclization with <span>l</span>-lysine but generates a more complex mixture with <span>d</span>-lysine. This difference in reactivity should contribute to the observed chemo- and enantioselectivty in the fluorescence response. This molecular probe can be used at 20 times lower concentration than a previously reported analog for lysine recognition. It has also displayed significantly enhanced enantioselectivity over the previously reported analog with the enantioselective fluorescence intensity ratio (ef) increased from 16.9 to 60.0 [ef = (I<sub>L</sub>-I<sub>0</sub>)/(I<sub>D</sub>-I<sub>0</sub>). I<sub>0</sub>: the fluorescence intensity of the probe in the absence of the amino acid].</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155959"},"PeriodicalIF":1.5,"publicationDate":"2026-01-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145922020","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}
Pub Date : 2026-01-02DOI: 10.1016/j.tetlet.2025.155958
Jianlong Chen , Caihe Sun , Yilin Bu , Xiaoyu Wang , Xia Zhao , Kui Lu
A visible-light-induced trifluoromethylation of alkenes was accomplished by using trifluoromethylsulfonylpyridinium salt, accompanied by the insertion of SO2 molecules. This reaction proceeded under the catalysis of Ir(ppy)3, resulting in the formation of trifluoromethylated 4H-benzo[e][1,2,4]thiadiazine-1,1-dioxides. The readily available reagents and the mild reaction conditions make this approach an efficient and cost effective method for the synthesis of these compounds.
{"title":"Photochemical trifluoromethylation of alkenes with trifluoromethylsulfonyl-pyridinium salt accompanied by SO₂ insertion: Synthesis of trifluoromethylated 4H-benzo[e][1,2,4]thiadiazine 1,1-dioxides","authors":"Jianlong Chen , Caihe Sun , Yilin Bu , Xiaoyu Wang , Xia Zhao , Kui Lu","doi":"10.1016/j.tetlet.2025.155958","DOIUrl":"10.1016/j.tetlet.2025.155958","url":null,"abstract":"<div><div>A visible-light-induced trifluoromethylation of alkenes was accomplished by using trifluoromethylsulfonylpyridinium salt, accompanied by the insertion of SO<sub>2</sub> molecules. This reaction proceeded under the catalysis of Ir(ppy)<sub>3</sub>, resulting in the formation of trifluoromethylated 4<em>H</em>-benzo[<em>e</em>][1,2,4]thiadiazine-1,1-dioxides. The readily available reagents and the mild reaction conditions make this approach an efficient and cost effective method for the synthesis of these compounds.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155958"},"PeriodicalIF":1.5,"publicationDate":"2026-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145922023","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}
Pub Date : 2026-01-02DOI: 10.1016/j.tetlet.2025.155957
Chihiro Sonoda, Takashi Hayashi
We report the synthesis and characterization of three new electron-deficient iron porphyrins bearing trifluoromethyl group substituents; FePormCF3, FePorβMe2(CF3)4 and FePorβEt2(CF3)4. FePormCF3, substituted with a CF3 group at the meso-position, and FePorβMe2(CF3)4, substituted with four CF3 and two methyl groups at the pyrrole β-positions, were synthesized via coupling of two dipyrromethane molecules, while FePorβEt2(CF3)4, where two methyl groups of FePorβMe2(CF3)4 were replaced with ethyl groups, was obtained through a biladiene-ac precursor route involving copper-templated cyclization. The corresponding free-base porphyrins were characterized by NMR and mass spectrometry, revealing clear electronic effects caused by the CF3 substituents. The 1H and 19F NMR spectra indicate downfield shifts of inner NHs, suggesting that the electron-withdrawing CF3 groups decrease the electron density of the porphyrin π-system and weaken the aromatic ring current. Differential pulse voltammetry measurements demonstrated positive shifts of the Fe(II)/Fe(III) redox potentials to −715 mV and −355 mV vs. Fc/Fc+ for FePormCF3 and FePorβMe2(CF3)4, respectively, confirming that introduction of the CF3 substituents effectively stabilizes the ferrous state. These results highlight how CF3 substitution modulates the electronic structure and redox properties of metalloporphyrins. In addition, it has been confirmed that these iron complexes can be incorporated into the myoglobin heme pocket. The present study establishes versatile synthetic approaches for introducing strong electron-withdrawing groups into heme analogues, in our efforts to develop useful attractive artificial cofactors with controlled redox potentials and unique reactivity.
{"title":"Synthesis and chemical properties of electron-deficient porphyrin cofactors with trifluoromethyl groups","authors":"Chihiro Sonoda, Takashi Hayashi","doi":"10.1016/j.tetlet.2025.155957","DOIUrl":"10.1016/j.tetlet.2025.155957","url":null,"abstract":"<div><div>We report the synthesis and characterization of three new electron-deficient iron porphyrins bearing trifluoromethyl group substituents; FePormCF<sub>3</sub>, FePorβMe<sub>2</sub>(CF<sub>3</sub>)<sub>4</sub> and FePorβEt<sub>2</sub>(CF<sub>3</sub>)<sub>4</sub>. FePormCF<sub>3</sub>, substituted with a CF<sub>3</sub> group at the <em>meso</em>-position, and FePorβMe<sub>2</sub>(CF<sub>3</sub>)<sub>4</sub>, substituted with four CF<sub>3</sub> and two methyl groups at the pyrrole β-positions, were synthesized via coupling of two dipyrromethane molecules, while FePorβEt<sub>2</sub>(CF<sub>3</sub>)<sub>4</sub>, where two methyl groups of FePorβMe<sub>2</sub>(CF<sub>3</sub>)<sub>4</sub> were replaced with ethyl groups, was obtained through a biladiene-<em>ac</em> precursor route involving copper-templated cyclization. The corresponding free-base porphyrins were characterized by NMR and mass spectrometry, revealing clear electronic effects caused by the CF<sub>3</sub> substituents. The <sup>1</sup>H and <sup>19</sup>F NMR spectra indicate downfield shifts of inner NHs, suggesting that the electron-withdrawing CF<sub>3</sub> groups decrease the electron density of the porphyrin π-system and weaken the aromatic ring current. Differential pulse voltammetry measurements demonstrated positive shifts of the Fe(II)/Fe(III) redox potentials to −715 mV and −355 mV vs. Fc/Fc<sup>+</sup> for FePormCF<sub>3</sub> and FePorβMe<sub>2</sub>(CF<sub>3</sub>)<sub>4</sub>, respectively, confirming that introduction of the CF<sub>3</sub> substituents effectively stabilizes the ferrous state. These results highlight how CF<sub>3</sub> substitution modulates the electronic structure and redox properties of metalloporphyrins. In addition, it has been confirmed that these iron complexes can be incorporated into the myoglobin heme pocket. The present study establishes versatile synthetic approaches for introducing strong electron-withdrawing groups into heme analogues, in our efforts to develop useful attractive artificial cofactors with controlled redox potentials and unique reactivity.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155957"},"PeriodicalIF":1.5,"publicationDate":"2026-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145922022","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}
Pub Date : 2025-12-31DOI: 10.1016/j.tetlet.2025.155953
Xu Chen , Haojie Ge , Jie Li
A novel synthesis of β-ketonitriles via base-promoted tandem reaction is presented herein. Simply combining N-acylpiperidin-2-one with NaN(SiMe3)2 enabled the preparation of a series of ketonitriles. This protocol is efficient, transition metal-free, mild, and operationally simple.
{"title":"NaN(SiMe3)2 promoted synthesis of β-ketonitriles with N-acylpiperidin-2-one and their cytotoxic activity on U87MG cells","authors":"Xu Chen , Haojie Ge , Jie Li","doi":"10.1016/j.tetlet.2025.155953","DOIUrl":"10.1016/j.tetlet.2025.155953","url":null,"abstract":"<div><div>A novel synthesis of β-ketonitriles via base-promoted tandem reaction is presented herein. Simply combining <em>N</em>-acylpiperidin-2-one with NaN(SiMe<sub>3</sub>)<sub>2</sub> enabled the preparation of a series of ketonitriles. This protocol is efficient, transition metal-free, mild, and operationally simple.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155953"},"PeriodicalIF":1.5,"publicationDate":"2025-12-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145922021","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}
In the present paper, Ullmann homocoupling reaction of bromobenzene derivatives by using various palladium complexes is chosen for the investigation of correlation between structure and properties. In this regard, novel palladium complexes with a series of para-substituted amidate ligands, N-(aryl)pyrazine-2-carboxamide, (aryl = 4-ethylphenyl, 4-nitrophenyl, 4-chlorophenyl, 4-fluorophenyl, 4-methoxyphenyl, 4-iodophenyl and 4-hydroxyphenyl are synthesized and structurally characterized. The experimental results prove that there is a linear correlation between the electron-withdrawing and -donating properties of the substituents and the catalytic activity. Furthermore, the clamshell or planar coordination geometry around the Pd center, exhibits a vital impact on the catalytic activity of the complexes. Our results show that among these various Pd(II) compounds, complex including methoxy substituent ligand displayed significant activity in Ullmann homocoupling reaction.
{"title":"The structure-property correlation in homocoupling reaction; a case study by clamshell and planar palladium complexes","authors":"Hassan Izadi , Alireza Abbasi , Ali Nemati Kharat , Hamid Reza Khavasi","doi":"10.1016/j.tetlet.2025.155955","DOIUrl":"10.1016/j.tetlet.2025.155955","url":null,"abstract":"<div><div>In the present paper, Ullmann homocoupling reaction of bromobenzene derivatives by using various palladium complexes is chosen for the investigation of correlation between structure and properties. In this regard, novel palladium complexes with a series of para-substituted amidate ligands, N-(aryl)pyrazine-2-carboxamide, (aryl = 4-ethylphenyl, 4-nitrophenyl, 4-chlorophenyl, 4-fluorophenyl, 4-methoxyphenyl, 4-iodophenyl and 4-hydroxyphenyl are synthesized and structurally characterized. The experimental results prove that there is a linear correlation between the electron-withdrawing and -donating properties of the substituents and the catalytic activity. Furthermore, the clamshell or planar coordination geometry around the Pd center, exhibits a vital impact on the catalytic activity of the complexes. Our results show that among these various Pd(II) compounds, complex including methoxy substituent ligand displayed significant activity in Ullmann homocoupling reaction.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155955"},"PeriodicalIF":1.5,"publicationDate":"2025-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145881187","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}
Pub Date : 2025-12-27DOI: 10.1016/j.tetlet.2025.155956
Fuzhong Han , Li Shi , Lina Jia , Xiangping Hu
An efficient Ru(II)-catalyzed 1,3,5-triazine group directed CH amidation protocol for anilines has been developed by employing dioxazolones as an amidating reagent. This protocol demonstrated remarkable substrate scope, smoothly converting a wide range of 1,3,5-triazine-fused aniline derivatives and diversely substituted dioxazolones variants into the corresponding products in good to excellent yields with good site selectivity and functional group tolerance. The reaction mechanism was performed using deuteration studies and control experiments, providing insights into the catalytic cycle.
{"title":"Ruthenium(II)-catalyzed 1,3,5-triazine group directed CH amidation of anilines with dioxazolones","authors":"Fuzhong Han , Li Shi , Lina Jia , Xiangping Hu","doi":"10.1016/j.tetlet.2025.155956","DOIUrl":"10.1016/j.tetlet.2025.155956","url":null,"abstract":"<div><div>An efficient Ru(II)-catalyzed 1,3,5-triazine group directed C<img>H amidation protocol for anilines has been developed by employing dioxazolones as an amidating reagent. This protocol demonstrated remarkable substrate scope, smoothly converting a wide range of 1,3,5-triazine-fused aniline derivatives and diversely substituted dioxazolones variants into the corresponding products in good to excellent yields with good site selectivity and functional group tolerance. The reaction mechanism was performed using deuteration studies and control experiments, providing insights into the catalytic cycle.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155956"},"PeriodicalIF":1.5,"publicationDate":"2025-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145881188","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}
Pub Date : 2025-12-27DOI: 10.1016/j.tetlet.2025.155954
Noé Martínez-Romero , Mario Valle-Sánchez , Diego Martínez-Otero , Horacio Reyes , Nelly Gonzalez-Rivas , Erick Cuevas-Yañez
An array of 1,1-diarylethylenes was obtained from the straightforward treatment of diverse 1,2-diaryl-2-azidoethan-1-ol derivatives with sulfuric acid. X-ray diffraction studies yielded unambiguous determinations of molecular structures of two representative compounds. A plausible reaction mechanism for this transformation involves generating a carbocation intermediate through alcohol dehydration. This is followed by concomitant aryl group 1,2-migration accompanied by the loss of nitrogen and HCN. These are the first examples of an intramolecular variant of the Schmidt reaction concerning a 1,2-azido alcohol.
{"title":"Denitrogenative dehydration-decyanation of 1,2-diaryl-2-azidoethan-1-ol derivatives: synthesis of 1,1-diarylethylenes","authors":"Noé Martínez-Romero , Mario Valle-Sánchez , Diego Martínez-Otero , Horacio Reyes , Nelly Gonzalez-Rivas , Erick Cuevas-Yañez","doi":"10.1016/j.tetlet.2025.155954","DOIUrl":"10.1016/j.tetlet.2025.155954","url":null,"abstract":"<div><div>An array of 1,1-diarylethylenes was obtained from the straightforward treatment of diverse 1,2-diaryl-2-azidoethan-1-ol derivatives with sulfuric acid. X-ray diffraction studies yielded unambiguous determinations of molecular structures of two representative compounds. A plausible reaction mechanism for this transformation involves generating a carbocation intermediate through alcohol dehydration. This is followed by concomitant aryl group 1,2-migration accompanied by the loss of nitrogen and HCN. These are the first examples of an intramolecular variant of the Schmidt reaction concerning a 1,2-azido alcohol.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155954"},"PeriodicalIF":1.5,"publicationDate":"2025-12-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145881321","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}
Pub Date : 2025-12-26DOI: 10.1016/j.tetlet.2025.155934
Yuta Inagaki, Shinnosuke Wakamori, Ryo Katsuta, Ken Ishigami
Efficient synthesis of the cyclic depsipeptide n-C14-surfactin was achieved using hydrophobic tag-assisted liquid-phase peptide synthesis (LPPS). Two linear synthetic routes, made possible by attaching the tag to the side-chain carboxyl group of either an aspartic acid or a glutamic acid residue, were examined, where both peptide elongation and macrocyclization proceeded with tag assistance. In addition to this prominent approach, an improved one-pot sequential coupling/deprotection protocol enabled decagram-scale synthesis, affording n-C14-surfactin with high chemical purity. The present strategy afforded significantly improved synthetic efficiency, with an excellent overall yield of 72 % over 13 steps, compared to previous solution- or solid-phase syntheses lacking support-based macrocyclization.
{"title":"Efficient synthesis of the cyclic lipopeptide n-C14-surfactin using soluble hydrophobic tag-assisted liquid-phase peptide synthesis","authors":"Yuta Inagaki, Shinnosuke Wakamori, Ryo Katsuta, Ken Ishigami","doi":"10.1016/j.tetlet.2025.155934","DOIUrl":"10.1016/j.tetlet.2025.155934","url":null,"abstract":"<div><div>Efficient synthesis of the cyclic depsipeptide <em>n</em>-C<sub>14</sub>-surfactin was achieved using hydrophobic tag-assisted liquid-phase peptide synthesis (LPPS). Two linear synthetic routes, made possible by attaching the tag to the side-chain carboxyl group of either an aspartic acid or a glutamic acid residue, were examined, where both peptide elongation and macrocyclization proceeded with tag assistance. In addition to this prominent approach, an improved one-pot sequential coupling/deprotection protocol enabled decagram-scale synthesis, affording <em>n</em>-C<sub>14</sub>-surfactin with high chemical purity. The present strategy afforded significantly improved synthetic efficiency, with an excellent overall yield of 72 % over 13 steps, compared to previous solution- or solid-phase syntheses lacking support-based macrocyclization.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"176 ","pages":"Article 155934"},"PeriodicalIF":1.5,"publicationDate":"2025-12-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"145837872","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}
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