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Mild decarboxylation of neat muconic acid to levulinic acid: a combined experimental and computational mechanistic study.
RSC Adv
December 2024
Department of Chemical and Biological Engineering, Iowa State University Ames IA 50011 USA +1-515-294-0625.
Levulinic acid (LA) is a key platform molecule with current applications in the synthesis of several commodity chemicals, including amino-levulinic acid, succinic acid, and valerolactone. In contrast to existing petroleum-based synthesis pathway, biomass-derived --muconic acid (MA) offers a sustainable route to synthesize LA. Here, we show the complete decarboxylation of neat MA to LA without solvent at atmospheric pressure and mild temperature.
View Article and Find Full Text PDFConstruction of Axially Chiral 4-Aminoquinolines by Cycloaddition and Central-to-Axial Chirality Conversion.
Org Lett
November 2024
Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an 710127, P. R. China.
A two-step strategy has been established for the enantioselective synthesis of 4-aminoquinolines possessing axial chirality. This approach involves a chiral phosphoric acid-catalyzed cycloaddition, followed by a DDQ oxidation step. The method offers efficient access to a variety of 1,1'-biaryl-2,2'-amino alcohol derivatives in excellent yields and enantioselectivities (up to 98% yield and 93% ee).
View Article and Find Full Text PDFSynthesis of Antitumor Bicyclic Hexapeptide RA-VII Analogues Possessing an Aromatic Amino Acid at Residue 2.
J Org Chem
November 2024
School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.
RA-III acetate was treated with Lawesson's reagent to afford [Tyr-3-Ψ(CS-NH)-Ala-4]RA-III acetate. Treatment of this product with Hg(OAc)/LiCO and then methanol gave an oxazole intermediate. Acid-catalyzed arylation of the methylene carbon atom on the oxazole ring and subsequent partial hydrolysis of the oxazole ring in the resultant compounds afforded RA-VII analogues having an aromatic amino acid at residue 2.
View Article and Find Full Text PDFMelt Polycondensation Strategy to Access Unexplored l-Amino Acid and Sugar Copolymers.
Biomacromolecules
November 2024
Department of Chemistry, Indian Institute of Science Education and Research (IISER Pune), Dr. Homi Bhabha Road, Pune 411008, Maharashtra, India.
Biodegradable polymers from bioresources are highly in demand for the development of sustainable polymer platforms for commodity plastics and in the biomedical field. Here, an elegant one-pot synthetic strategy is developed, for the first time, to access unexplored hybrid polymers from two naturally abundant resources: carbohydrates (sugars) and l-amino acids. A bottleneck in the synthetic strategy is overcome by tailor-making d-mannitol-based six- and five-membered bicyclic acetalized diols, and their structures are confirmed by single-crystal X-ray diffraction and 2D NMR spectroscopy.
View Article and Find Full Text PDFSyntheses of Novel Spirobenzazepinoindole Derivatives via Lewis-Acid Catalyzed Pictet-Spengler Cyclization.
Chem Asian J
December 2024
Organic and Bio-Organic Chemistry laboratory, CSIR-Central Leather Research Institute (CSIR-CLRI), Chennai, 600020, India.
The syntheses of novel spirobenzazepinoindole derivatives has been achieved through a highly efficient and synthetic route. The approach involves a two-step reaction, utilizing indole derivatives, 2-amino benzyl alcohol, and ninhydrin as key starting materials under mild reaction conditions. The reaction proceeds via a sequential cascade process involving cyclization, condensation and spiro-annulation, leading to the formation of the spirobenzazepinoindole core structure in good to excellent yields.
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