Total Synthesis of Darobactin A

Total Synthesis of Darobactin A

The collaborative total synthesis of darobactin A, a recently isolated antibiotic that selectively targets Gram-negative bacteria, has been accomplished in a convergent fashion with a longest linear sequence of 16 steps from d-Garner’s aldehyde and l-serine. Scalable routes toward three non-canonica...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 144; no. 31; pp. 14026 - 14030
Main Authors: Nesic, Marko, Ryffel, David B., Maturano, Jonathan, Shevlin, Michael, Pollack, Scott R., Gauthier, Donald R., Trigo-Mouriño, Pablo, Zhang, Li-Kang, Schultz, Danielle M., McCabe Dunn, Jamie M., Campeau, Louis-Charles, Patel, Niki R., Petrone, David A., Sarlah, David
Format: Journal Article
Language:English
Published: American Chemical Society 10-08-2022
Online Access:Get full text
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Summary:The collaborative total synthesis of darobactin A, a recently isolated antibiotic that selectively targets Gram-negative bacteria, has been accomplished in a convergent fashion with a longest linear sequence of 16 steps from d-Garner’s aldehyde and l-serine. Scalable routes toward three non-canonical amino acids were developed to enable the synthesis. The closure of the bismacrocycle was realized through sequential, halogen-selective Larock indole syntheses, where the proper order of cyclizations proved crucial for the formation of the desired atropisomer of the natural product.
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ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.2c05891