Synform issue 2024/04
Synlett 2024; 35: A53-A69 DOI: 10.1055/s-0040-1720628 Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents (Source: Synlett)
Source: Synlett - March 13, 2024 Category: Chemistry Authors: Zanda, Matteo Tags: Synform Source Type: research
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Synlett 2024; 35: V- DOI: 10.1055/s-0043-1763694 Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents (Source: Synlett)
Source: Synlett - March 13, 2024 Category: Chemistry Tags: table of contents Source Type: research
Photoinduced Direct Carbamoylation of Ethers with Isocyanates towards the Synthesis of α-Amide-Substituted Ether Derivatives
Synlett DOI: 10.1055/a-2272-8045 Photoinduced carbamoylation of ethers using isocyanates as amide sources was accomplished under mild and environmentally friendly reaction conditions. A series of isocyanates were tolerated in this protocol to construct α-amide-substituted ether derivatives with desired yields. The method featured broad substrate scope and good functional group tolerance, which could play an important role in the construction of biological molecules with ethers. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | F...
Source: Synlett - March 11, 2024 Category: Chemistry Authors: Qi, Ming Li, Jing-Han Lu, Xiao-Jie Xu, An-Wu Tags: letter Source Type: research
Synthesis of Racemosin B and Its Analogues by a Photochemical Cyclization
Synlett DOI: 10.1055/a-2271-7324 A simple approach for the synthesis of the alkaloid racemosin B has been developed through a photochemical cyclization reaction with a 33% overall yield without any reagents. This method is sustainable and environmentally friendly because no reagents are required to effect the transformation. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synlett)
Source: Synlett - March 6, 2024 Category: Chemistry Authors: Wazir, Irfan Nagarajan, Rajagopal Tags: letter Source Type: research
Catalytic Chain Transfer in Crosslinking Photopolymerizations
Synlett DOI: 10.1055/a-2256-2980 Presented here is a detailed account of the development and implementation of macrocyclic cobaloxime complexes as sulfur-free, catalytic chain transfer agents (CTAs) in crosslinking photopolymerizations. Although much of this review is dedicated to understanding the fundamentals of catalytic chain transfer (CCT) in photopolymerizations, its impact on network topology and resultant mechanical properties, future goals of applying this technology to multimaterial 3D printing are also discussed. It is our long-term ambition for catalytic, sulfur-free CTAs to supplant existing consumptive, sulfu...
Source: Synlett - March 5, 2024 Category: Chemistry Authors: Bagnall, Nicholas R. Jones, Meredith H. Donovan, Brian R. Worrell, Brady T. Tags: synpacts Source Type: research
Validation and Application of an Innovative Protective Group Concept: Enhancing Substrate Reactivity in Glycosylations by Disrupting Intermolecular Interactions
Synlett DOI: 10.1055/a-2269-7680 We have established an innovative protective approach that disrupts intermolecular interactions to enhance substrate reactivity. Specifically, diacetylimide protection of acetamide prevents the formation of hydrogen bonds, while the incorporation of tert-butyl groups on the aromatic protecting group disrupts π-stacking interactions, both of which culminate in heightened reactivity in glycosylations. We explored the synergistic implementation of these protective measures and applied them to the synthesis of 6-sulfo sialyl Lewis X. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stutt...
Source: Synlett - March 5, 2024 Category: Chemistry Authors: Yano, Kumpei Yoshimoto, Takuya Tsutsui, Masato Manabe, Yoshiyuki Fukase, Koichi Tags: letter Source Type: research
Trideuteromethylation of Alkyl and Aryl Bromides by Nickel-Catalyzed Electrochemical Reductive Cross-Electrophile Coupling
Synlett DOI: 10.1055/s-0042-1751558 A new nickel-catalyzed electrochemical, reductive cross-coupling for the trideuteromethylation of alkyl and aryl bromides is reported in which CD3 arenesulfonate derivatives were used as effective and readily available CD3 sources. The CD3-labeled products were obtained with good yields. It was demonstrated that this methodology is scalable and can be efficiently used for various methylations, including 13CH3 and 13CD3 labeling. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synlett)
Source: Synlett - March 4, 2024 Category: Chemistry Authors: Steverlynck, Joost Sitdikov, Ruzal Nikolaienko, Pavlo Kale, Ajit Prabhakar Rueping, Magnus Tags: letter Source Type: research
Fragments Synthesis of A. baumannii ATCC 17961 O-Antigen
Synlett DOI: 10.1055/a-2272-8163
Acinetobacter baumannii can cause many diseases including septicemia, pneumonia, meningitis, soft tissue, and urinary tract infections. Herein, we described the synthesis of one trisaccharide and two tetrasaccharide fragments derived from A. baumannii ATCC 17961 O-antigen that can be used for screening novel glyco-epitopes and for developing a synthetic carbohydrate-based vaccine against A. baumannii infection. The overall yields for the synthesis of the desired trisaccharide 1, tetrasaccharide 2, and tetrasaccharide 3 are 26.8% (8 steps), 21.6% (9 steps), and 24.5% (6 steps), respec...
Source: Synlett - March 4, 2024 Category: Chemistry Authors: Li, Xinxin Duan, Liangshen Liu, Deyong Qi, Jianying Wang, Liming Zhang, Qingju Tags: letter Source Type: research
The FeBr3-Catalyzed Transfer Hydrogenation of Styrene Derivatives under Mild Reaction Conditions
Synlett DOI: 10.1055/s-0042-1751572 The transfer hydrogenation of alkenes was realized by using a simple transition-metal compound (FeBr3) and 1,4-cyclohexadiene (1,4-CHD) as the hydrogen donor. The conversion of a number of di- and trisubstituted alkenes was investigated, and even a tetrasubstituted alkene was successfully converted. Compared with previously published work with the more expensive InBr3, the reaction times were considerably reduced and significantly milder reaction conditions could be applied. Interestingly, a transformation that was catalytic in 1,4-CHD, with molecular hydrogen as a stoichiometric reducin...
Source: Synlett - March 1, 2024 Category: Chemistry Authors: Kail, Sascha Hilt, Gerhard Tags: letter Source Type: research
Sulfonium-Based Activity-Based Probes for Lysine-Selective Protein Profiling under Alkaline Conditions
In this study, we constructed a series of sulfonium-based small molecules to react with the amine group of lysine residues by utilizing the strong electrophilicity of sulfonium, resulting in lysine-selective labeling via the formation of classical amide bonds under alkaline conditions (pH 9.0–11.0). After systematic optimization of the labeling conditions, this strategy was utilized for protein labeling across various bacteria’s lysates. Finally, combined with the activity-based protein profiling (ABPP) strategy, we successfully identified and analyzed hundreds of labeled lysine residues in the bacterial proteome. [......
Source: Synlett - March 1, 2024 Category: Chemistry Authors: Hu, Changxing Wang, Rui An, Yuhao Wan, Chuan Yin, Feng Lu, Fei Li, Zigang Tags: letter Source Type: research
Enzymatic Synthesis of Hydroxycinnamic Acid Amides in Water Using the Promiscuous Hydrolase/Acyltransferase PestE from Pyrobaculum calidifontis VA1
Synlett DOI: 10.1055/a-2268-8035 Hydroxycinnamic acid amides are believed to have antioxidant, antidiabetic, cytotoxic, anticancer, neuroprotective, and antiinflammatory properties, making them interesting target molecules for potential applications in the food, cosmetics, and pharmaceutical industries. Here, we describe the synthesis of hydroxycinnamic acid amides starting from hydroxycinnamic acid esters and the corresponding amines by using variants of the promiscuous hydrolase/acyltransferase from Pyrobaculum calidifontis VA1 (PestE) in water as a solvent. Up to 97% conversion within two hours at 60 °C was achieved wi...
Source: Synlett - March 1, 2024 Category: Chemistry Authors: Baumert, Benjamin Terholsen, Henrik Cziegler, Clemens Thier, Isabel Badenhorst, Christoffel P. S. Siems, Karsten Bornscheuer, Uwe T. Tags: letter Source Type: research
Organic Photoredox Carbonylation of Arenediazonium under Mild Conditions
Synlett DOI: 10.1055/s-0042-1751531 The modular synthesis of diverse carbonyl compounds is at the heart of organic synthesis. An optimized protocol for photoredox carbonylation was developed that operates under milder conditions with mesitylacridinium as a photocatalyst. Arenediazonium salts were converted into benzoates (with alcohols), benzoic acids (with water), benzamides (with amines), and chlorides (with 1-butyl-3-methylimidazolium chloride) at 20 bar CO and 20 °C. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synlett)
Source: Synlett - February 29, 2024 Category: Chemistry Authors: Stuhr, Robin Jacobi von Wangelin, Axel Tags: letter Source Type: research
Modification of an N-Methyl Group toward a New Energetic Melt-Castable Material with a Good Energy-Stability Balance
In this study, we selected the 4-methoxy-3,5-dinitropyrazole framework and a stable nitro group to design a new energetic melt-castable compound, namely 4-methoxy-3,5-dinitro-1-(nitromethyl)-1H-pyrazole (MDNNMP). Compared with the N-methylation product DMDNP and the nitrato-substituted derivative MC-7, MDNNMP exhibits a better balanced performance, including good thermal stability (Td
: 203.7 °C), detonation velocity (Dv
: 8099 m s–1) and impact sensitivity (20 J). The favorable balanced performance of MDNNMP suggests that it is a suitable candidate as a high-performance melt-castable material. Additionally,...
Source: Synlett - February 28, 2024 Category: Chemistry Authors: Chen, Fang Song, Siwei Zhang, Qinghua Wang, Yi Tags: letter Source Type: research
Manganese(I)-Catalyzed C –H Allylation of Tryptophans and Their Oligopeptides On Water
Synlett DOI: 10.1055/a-2268-4678 The manganese(I)-catalyzed allylation of the amino acid tryptophan is realized under exceedingly mild conditions using water as a sustainable and non-hazardous reaction medium, instead of classical organic solvents, with great potential for green and sustainable chemistry. Synthetically useful α,β-unsaturated esters can be accessed by reaction with Morita–Baylis–Hillman (MBH) adducts following a fast C–H activation approach. The robustness of this procedure is reflected by kinetic analysis at different reaction temperatures and reduced catalyst loadings are employed. [...] Georg Thi...
Source: Synlett - February 27, 2024 Category: Chemistry Authors: Struwe, Julia Oyama, Tsuyoshi Gallou, Fabrice Ackermann, Lutz Tags: letter Source Type: research
Errata Practical and Scalable Total Syntheses of (+)-Dysidavarones A –C
Synlett 2024; 35: e2-e2 DOI: 10.1055/s-0043-1763686 Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Full text (Source: Synlett)
Source: Synlett - February 27, 2024 Category: Chemistry Authors: Kuang, Yang Chang, Le Wang, Bingjian Kang, Jingyi Chong, Chuanke Lu, Zhaoyong Tags: errata Source Type: research
