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Updated: Sep 15, 2025

Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library
Published on: June 20, 2014
Design and Synthesis of a 3-Arylenoyltetramic Acid Library Employing a Consecutive Three-Component Coupling
Miho Yoshiki1,2, Shiori Koyama3, Hironao Kobayashi4
1Graduate School of Pharmaceutical Sciences, Hoshi University, 2-4-41 Ebara, Shinagawa-ku, Tokyo 142-8501, JAPAN.
Abstract:
A facile method for synthesizing 3-arylenoyltetramic acids using consecutive coupling of a newly designed iodovinyldioxinone, arylboronic acids, and protected amino acids was established. The iodovinyldioxinone first undergoes Suzuki-Miyaura coupling with various arylboronic acids at room temperature to give 6-substituted dioxinones. These dioxinones generate acylketenes on heating, which react with protected amino acids followed by Lacey-Dieckmann cyclization to produce various 3-arylenoyltetramic acids. The scope and limitations of the developed method, as well as the antibiotic activity of the resultant 3-arylenoyltetramic acids toward methicillin-resistant S. aureus strains, were evaluated.
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Acidity of 1-Alkynes
The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
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