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A regiospecific synthesis of a series of 1-sulfonyl azepinoindoles as potent 5-HT6 ligands is reported.
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http://dx.doi.org/10.1016/j.bmcl.2008.06.030 | DOI Listing |
Chem Commun (Camb)
September 2025
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
A CFOH-catalysed tandem cyclization of -alkynylnaphthols and -quinone monoketals is disclosed. The CFOH catalyst activates alkynylnaphthol to generate an all-carbon tetrasubstituted VQM by nucleophilic addition to quinone monoketal (Michael addition). Furthermore, the CFOH catalyst triggers -quinone monoketal to generate an electrophilic oxocarbenium cation to be captured by -alkynylnaphthol regiospecifically, resulting in the formation of an all-carbon tetrasubstituted VQM, followed by an intramolecular cyclization to afford a series of 1-(3-arylbenzofuran-2-yl)naphthalen-2-ols.
View Article and Find Full Text PDFOrg Biomol Chem
August 2025
Technical Institute of Fluorochemistry (TIF), Institute of Advanced Synthesis (IAS), School of Chemistry and Molecular Engineering, State Key Laboratory of Material-Oriented Chemical Engineering, Nanjing Tech University, 30 South Puzhu Road, Nanjing 211816, P. R. China.
The dehydroxyfluorination of allylic alcohols stands as one of the most direct and effective methods for synthesizing versatile allylic fluorides. However, regioselectivity control in this transformation remains challenging. Herein, we demonstrate a fluorine effect-induced regiospecific dehydroxyfluorination of 3,3-difluoroallyl alcohols using Olah's reagent under mild reaction conditions.
View Article and Find Full Text PDFInt J Biol Macromol
September 2025
Department of Drug Science and Technology, University of Turin, Turin, Italy. Electronic address:
The high-fat content of hazelnuts, mainly triglycerides, makes them prone to lipid oxidation during storage, which has a big impact on their sensory and nutritional quality. The chemical pathways leading to hazelnut oxidative rancidity have been well characterized and are faster on free fatty acids. Lipase(s) enzymes are required in oilseeds to hydrolyse the ester bonds to free the single molecule of fatty acids.
View Article and Find Full Text PDFNat Commun
July 2025
State Key Laboratory of Chemical Biology, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China.
Chiral N-heterocycles such as piperidines and tetrahydroisoquinolines are privileged structural motifs in drug discovery and pharmaceutical industry. The development of efficient and practical asymmetric synthetic methods towards pharmaceutically important chiral N-heterocycles constitutes an important subject in synthetic chemistry. Asymmetric synthesis of 2,3-cis-disubstituted piperidines bearing two consecutive chiral centers is particularly challenging in terms of both diastereoselective and enantioselective control.
View Article and Find Full Text PDFMethods Enzymol
July 2025
School of Chemistry & Biochemistry, Georgia Institute of Technology, Atlanta, GA, United States; School of Biological Sciences, Georgia Institute of Technology, Atlanta, GA, United States. Electronic address:
While halogenation is one of the most versatile C-H functionalization strategy, regiospecific halogenation of peptides and proteins is outside the purview of traditional chemical catalysis. Enzymes that participate in the biosynthesis of ribosomally synthesized and post-translationally modified peptides and proteins can bridge this gap and offer a biocatalytic route for residue-specific incorporation of halogen handles onto amino acid side chains. Protocols described herein provide a guided approach for the discovery of peptide halogenases in the context of natural product biosynthetic gene clusters, and the preliminary reconstitution of their activity using a bacterial heterologous host.
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