Journal
ORGANIC LETTERS
Volume 19, Issue 14, Pages 3771-3774Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01629
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Funding
- JSPS [25293026]
- Scientific Research on Innovative Areas Chemical Biology of Natural Products [24102502]
- Ministry of Education, Culture, Sports, Science and Technology through Program for Leading Graduate Schools (Hokkaido University Ambitious Leader's Program)
- Takeda Science Foundation
- Platform Project for Supporting Drug Discovery and Life Science Research (Platform for Drug Discovery, Informatics and Structural Life Science)
- Grants-in-Aid for Scientific Research [16H04180, 17J04794, 16H05097] Funding Source: KAKEN
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The total synthesis of plusbacin A(3) (1) has been accomplished wing a solvent-dependent diastereodivergent Joullie-Ugi three-component reaction (JU-3CR) as a key Step. Two trans-3-hydroxy-L-proline residues were constructed by combining the JU-3CR with a convertible isocyanide strategy Subsequent peptide coupling and macrolactamization afforded plusbacin A(3). Investigating the antibacterial activity of 1 compared with that of its dideoxy analogue revealed that the tlirco-beta- hydroxyaspartic acid residues are essential for antibacterial aCtivity. Notably, there is a low potential for the development of resistance in S. aureus against plusbacin A(3).
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