Diesters obtained from diacids produced by oxidative ring cleavage of cycloadducts derived from acyl-nitroso compounds and cyclic 1,3-dienes undergo highly regioselective hydrolysis on reaction with lithium hydroperoxide, which allows for easy differentiation of the carboxyl groups leading to a new approach to polyoxamic acid.
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Int J Mol Sci
December 2023
Univ. Lille, Inserm, Institut Pasteur de Lille, U1177-Drugs and Molecules for Living Systems, F-59000 Lille, France.
Historically, natural products have played a major role in the development of antibiotics. Their complex chemical structures and high polarity give them advantages in the drug discovery process. In the broad range of natural products, sesquiterpene lactones are interesting compounds because of their diverse biological activities, their high-polarity, and sp-carbon-rich chemical structures.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
September 2021
Institut für Chemie, Universität Oldenburg, Carl-von-Ossietzky-Straße 9-11, 26111, Oldenburg, Germany.
The acyl nitroso Diels-Alder reaction of 1,3-dienes with electrochemically oxidised hydroxamic acids is described. By using alternating current electrolysis, their typical electro-induced decomposition could be suppressed in favour of the 1,2-oxazine cycloaddition products. The reaction was optimised using Design of Experiments (DoE) and a sensitivity test was conducted.
View Article and Find Full Text PDFOrg Lett
May 2020
School of Pharmaceutical Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
Org Lett
January 2019
Department of Chemistry , Michigan State University, East Lansing , Michigan 48824 , United States.
The selective oxidation of C2-alkyl-substituted indoles to 3-oxindole and the selective C-H oxygenation or amination of C2,C3-dialkyl-substituted indoles at C2 are reported under mild conditions. The position of the alkyl substitution on the indole directs the reaction to different pathways under similar conditions.
View Article and Find Full Text PDFJ Phys Chem A
September 2018
Institute of Chemistry, The Accelerator Laboratory , The Hebrew University of Jerusalem, Jerusalem 91904 , Israel.
Acyl nitroso compounds or nitrosocarhonyls (RC(O)N═O) are reactive short-lived electrophiles, and their hydrolysis and reactions with nucleophiles produce HNO. Previously, direct detection of acyl nitroso species in nonaqueous media has been provided by time-resolved infrared spectroscopy demonstrating that its half-life is about 1 ms. In the present study hydroxamic acids (RC(O)NHOH) are oxidized electrochemically in buffered aqueous solutions (pH 5.
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