Article
Chemistry, Organic
Timea Szabo, Funda Lidya Gorur, Simon Horvath, Balazs Volk, Matyas Milen
Summary: A new synthetic approach for the total synthesis of the pharmacologically active beta-carboline alkaloid brevicolline is described. The method allows for the practical synthesis of the racemic target molecule, the natural (S)-enantiomer, and its antipode. The synthetic route has been developed to improve the overall yield compared to previously reported methods.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Ouldouz Ghashghaei, Marina Pedrola, Francesca Seghetti, Victor V. Martin, Ricardo Zavarce, Michal Babiak, Jiri Novacek, Frederick Hartung, Katharina M. Rolfes, Thomas Haarmann-Stemmann, Rodolfo Lavilla
Summary: The participation of reactants in polarity inversion allows the continuation of productive domino processes in multicomponent reactions, leading to the discovery of novel reaction pathways and various polyheterocyclic scaffolds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Srinivas Beduru, Andrei G. Kutateladze
Summary: Excited State Intramolecular Proton Transfer (ESIPT) is a powerful synthetic tool that offers rapid access to complex polyheterocycles. This study demonstrates that sulfonamides can serve as proton donors in ESIPT-initiated photoinduced reactions, leading to the synthesis of polyheterocyclic molecular cores with fused cyclic sulfonamide moieties.
Article
Chemistry, Organic
Dong-Lin Zhao, Xue-Yan Huo, Pan-Pan Li, Xiao-Long Yuan, Sheng-Ying Li, Lei Du, Li-Jun Huang, Peng Zhang
Summary: In this study, a novel Prenylated indole alkaloid (PIA) with unique structure was isolated from the endophytic fungus of Nicotiana tabacum. The compound showed significant anti-inflammatory activity.
Article
Chemistry, Organic
Hao-Cong Li, Guan-Nan Li, Kai Sun, Xiao-Lan Chen, Ming-Xuan Jiang, Ling-Bo Qu, Bing Yu
Summary: A Ce(III)-photocatalyzed method for synthesizing amides from carboxylic acids and aryl isocyanates was developed. The reaction involves the formation of alkyl radicals from carboxylic acids followed by their addition to the electron-deficient carbon.
Article
Pharmacology & Pharmacy
Lingyan Wang, Guiyang Xia, Huan Xia, Xiaohong Wei, Yanan Wang, Sheng Lin
Summary: A chemical investigation on the aqueous extract of Corydalis yanhusuo tubers led to the isolation and structural elucidation of three pairs of trace enantiomeric hetero-dimeric alkaloids. These compounds exhibited potent inhibition of NO production and antinociceptive effects.
ACTA PHARMACEUTICA SINICA B
(2023)
Article
Chemistry, Organic
Marta Papis, Camilla Loro, Michele Penso, Gianluigi Broggini, Francesca Foschi
Summary: The synthesis of modified morpholino monomers was achieved through condensation reactions under Lewis acid conditions, utilizing a simple and efficient method to access diversified optically pure morpholino monomers with high yields and anomeric ratios.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Li-Xuan Li, Long Min, Tian-Bing Yao, Shu-Xiao Ji, Chuang Qiao, Pei-Lin Tian, Jianwei Sun, Chuang-Chuang Li
Summary: The first total synthesis of daphgraciline, a member of Daphniphyllum yuzurine-type alkaloids, has been achieved. The unique structure of the yuzurine-type subfamily was efficiently assembled using a novel method, and the complex skeleton and key moiety were successfully constructed. This study provides a foundation for the further synthesis of enantioenriched daphgraciline with high stereochemistry.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Niklas Reinfandt, Christoph Schoo, Luis Duetsch, Ralf Koeppe, Sergey N. Konchenko, Manfred Scheer, Peter W. Roesky
Summary: A series of 4d/4f-polyarsenides, -polyarsines and -polystibines were obtained through reduction reactions, with unique properties observed in the products of Mo-stibide and Mo-arsenide, showing planar tetrastibacyclobutadiene and tetraarsacyclobutadiene ligands.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Multidisciplinary Sciences
Stone Woo, Ryan A. Shenvi
Summary: The ingestion of alkaloid metabolites from the bark of Galbulimima tree can lead to psychotropic and excitatory effects in humans. However, the limited supply of these alkaloids has hindered their exploration and development. In this study, researchers report a solution to the supply problem of GB18, a unique compound found in Galbulimima bark that is believed to have psychotropic effects. By developing new chemical reactions, the researchers were able to synthesize a large amount of GB18 and found it to be a potent antagonist of kappa- and mu-opioid receptors. This discovery opens up new possibilities for understanding the biological activity of Galbulimima metabolites.
Article
Chemistry, Organic
Jianquan Zhu, Chao Zhang, Luyi Liu, Chaoyun Xue, Yukun Cai, Xiao-Yu Liu, Fei Xue, Yong Qin
Summary: This paper presents an asymmetric total synthesis of the sarpagine alkaloid (-)-normacusine B. The key features of this synthesis include a photocatalytic nitrogen-centered radical cascade reaction, a titanium-mediated intramolecular amide-alkene coupling, and a nickel-catalyzed reductive Heck coupling.
Article
Chemistry, Multidisciplinary
Artyom E. Paromov, Sergey Sysolyatin
Summary: In this study, an acid-catalyzed condensation reaction was explored between glyoxylic acid or its ester and carboxamides or mesyl amide, resulting in the formation of diaminoacetic acid derivatives. The use of elemental iodine as the acid catalyst was found to be more effective in yielding the derivatives compared to p-toluenesulfonic acid. The activity of mesyl amide during condensation with ethyl glyoxylate was notably high, indicating a potential influence of the sulfonyl moiety in the amide molecule on the condensation process.
Article
Chemistry, Organic
Letizia Molteni, Egle M. Beccalli, Laura Castoldi, Gianluigi Broggini, Camilla Loro
Summary: This study presents an efficient method for the synthesis of 1,3-polyheterocyclic systems using copper catalysts and oxidative conditions. Methanol is utilized as both a solvent and a reagent, making the process highly efficient and sustainable.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Hongbin Zhai, Zhenhua Wang, Kewei Chen, Tian-Yu Sun, Jian Wei, Yun-Dong Wu
Summary: The first asymmetric total synthesis of indole alkaloid arbophyllidine has been achieved, featuring key reactions such as intramolecular reductive Heck reaction, Fischer indolization, and oxidative lactonization. Density functional theory calculations were employed to provide a comprehensive understanding of the oxidative lactonization.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Biotechnology & Applied Microbiology
Kai Zhang, Yuanzhi He, Jiawei Zhu, Qi Zhang, Luyao Tang, Li Cui, Yan Feng
Summary: Reductive aminases (RedAms) from Aspergillus calidoustus (AcRedAm) and bacteria (BaRedAm) demonstrated high conversion rates for synthesizing secondary amines using a wide range of ketone and amine substrates. By rational design, AcRedAm was engineered to produce highly stereoselective mutants capable of synthesizing (R)-rasagiline with >99% enantiomeric excess. These features highlight the potential of AcRedAm and BaRedAm for further research and expanding the biocatalytic toolbox for industrial applications.
FRONTIERS IN BIOENGINEERING AND BIOTECHNOLOGY
(2021)
