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Cobalt-Catalyzed Enantioselective Reductive Coupling of Imines and Internal Alkynes.
Angew Chem Int Ed Engl
January 2025
IISER Kolkata: Indian Institute of Science Education and Research Kolkata, Department of Chemical Sciences, Mohanpur, 741246, Nadia, INDIA.
Chiral allyl amines are important structural components in natural products, pharmaceuticals, and chiral catalysts. Herein, we report a cobalt-catalyzed enantioselective reductive coupling of imines with internal alkynes to synthesize chiral allyl amines. The reaction is catalyzed by a cobalt complex derived from commercially available bisphosphine ligand utilizing zinc as the electron donor.
View Article and Find Full Text PDFExperimental and Computational NMR Studies of Large Alkaloids Exemplified With Vindoline Trimer: Advantages and Limitations.
Magn Reson Chem
January 2025
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Irkutsk, Russia.
The complete H and C NMR assignments of a trimeric vindoline together with its individual components, dimeric vindolicine and monomeric vindoline, are performed based on a thorough analysis of the ROESY, COSY, HSQC, and HMBC spectra in combination with the state-of-the-art quantum-chemical calculations. A spatial structure of vindoline trimer is determined by means of computational conformational analysis in combination with the probability distribution map of its basic conformers. On the example of monoterpene indole alkaloid, the trimer vindoline, the present study reveals the power of modern computational NMR to perform identification and stereochemical studies of large natural compounds with some limitations, which may arise in the quantum chemical computing workflow.
View Article and Find Full Text PDFTotal Synthesis of Exiguolide Stereoisomers: Impact of Stereochemical Permutation on Reactivity, Conformation, and Biological Activity.
J Org Chem
December 2024
Department of Applied Chemistry, Faculty of Science and Engineering, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan.
(-)-Exiguolide is a marine macrolide natural product with potent anticancer activity. In this study, the total synthesis of exiguolide stereoisomers, (9)-exiguolide, (9,13)-exiguolide, and (9,13,19)-exiguolide, was achieved by capitalizing on our macrocyclization/transannular pyran cyclization strategy. The impact of the stereochemical permutation on the reactivity of advanced intermediates, the conformation of the macrocyclic skeleton, and the antiproliferative activity against human cancer cells were investigated in detail.
View Article and Find Full Text PDFSurface Decoration of Cellulose With Trifluoromethylphenyl Substituted Thiourea: A Robust Hydrogen-Bonding Catalyst in Conjunction With L-Proline for the Asymmetric Direct Mannich Reaction.
Biopolymers
January 2025
Department of Chemistry, Faculty of Engineering and Science, Bursa Technical University, Bursa, Turkey.
Cellulose is one of the most abundant biopolymers in nature. Despite being the subject of research in various fields, it is not as famous as chitosan in catalyst design. Herein, a novel thiourea-functionalized cellulose (CTU-6) was synthesized as a robust hydrogen bonding catalyst with the degree of substitution (DS) of 0.
View Article and Find Full Text PDFUnmasking the reverse catalytic activity of 'ene'-reductases for asymmetric carbonyl desaturation.
Nat Chem
January 2025
Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, Department of Chemistry, School of Science and Research Center for Industries of the Future, Westlake University, Hangzhou, China.
Article Synopsis
- Carbonyl desaturation is a key reaction in organic synthesis, but traditional methods often require complicated multi-step processes or harsh conditions.
- Researchers developed a new biocatalytic system using engineered 'ene'-reductases to streamline the desaturation of cyclohexanones into cyclohexenones, ensuring better stereochemical control.
- This method operates under mild conditions, uses air for oxidation, and shows improved tolerance to sensitive functional groups and greater stereoselectivity compared to conventional catalysts.
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