Total Synthesis of Dynobactin A

The first total synthesis of the potent antimicrobial agent dynobactin A is disclosed. This synthesis enlists a singular aziridine ring opening strategy to access the two disparate β-aryl-branched amino acids present within this complex decapeptide. Featuring a number of unique maneuvers to navigate...

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Bibliographic Details
Published inJournal of the American Chemical Society Vol. 146; no. 10; pp. 6444 - 6448
Main Authors Schneider, Fabian, Guo, Yinliang, Lin, You-Chen, Eberle, Kelly J., Chiodi, Debora, Greene, Johnathan A., Lu, Chenxin, Baran, Phil S.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 13.03.2024
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
MEMBRANE
DISCOVERY
MACHINERY
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Summary:The first total synthesis of the potent antimicrobial agent dynobactin A is disclosed. This synthesis enlists a singular aziridine ring opening strategy to access the two disparate β-aryl-branched amino acids present within this complex decapeptide. Featuring a number of unique maneuvers to navigate inherently sensitive and epimerizable functional groups, this convergent approach proceeds in only 16 steps (LLS) from commercial materials and should facilitate the synthesis of numerous analogues for medicinal chemistry studies.
Bibliography:ObjectType-Article-1
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ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/jacs.3c11560