Design and Synthesis of a 3-Arylenoyltetramic Acid Library Employing a Consecutive Three-Component Coupling
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 <i>S. aureus</i> strains, were evaluated.
Authors
- Naoki Kanoh (ORCID: https://orcid.org/0000-0002-4382-3715)
- Junko Fujimoto
- Kazutada Ikeuchi (ORCID: https://orcid.org/0000-0001-5343-3502)
- Titov Ri
- Hiromasa Yokoe (ORCID: https://orcid.org/0000-0002-3326-7938)
- Hiromichi Nishiyama (ORCID: https://orcid.org/0000-0003-0439-0002)
- H Kobayashi
- Masako Honsho
- Yusuke Sasano (ORCID: https://orcid.org/0000-0002-3852-8607)
- Yukihiro Asami (ORCID: https://orcid.org/0000-0003-1821-9169)
- Aoi Kimishima (ORCID: https://orcid.org/0000-0002-2625-1356)
- Shunsuke MIMURA
- Yoshiharu Iwabuchi
- Sen Koyama
- Miho Yoshiki
Institutions
- Tohoku University (JP)
- Zen-Noh (Japan) (JP)
- Hoshi University (JP)
- Kitasato Institute Hospital (JP)
- Kitasato University (JP)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-07-14
- DOI
- https://doi.org/10.1021/acs.joc.5c00998
- Primary Topic
- Chemical Synthesis and Analysis
- Type
- article
- Field-Weighted Citation Impact
- 0.00