Total Synthesis of Darobactin A

Marko Nesic, David B. Ryffel, Jonathan Maturano, Michael Shevlin, Scott R. Pollack, Donald R. Gauthier, Pablo Trigo-Mouriño, Li Kang Zhang, Danielle M. Schultz, Jamie M. McCabe Dunn, Louis Charles Campeau, Niki R. Patel, David A. Petrone, David Sarlah

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish (US)
Pages (from-to)14026-14030
Number of pages5
JournalJournal of the American Chemical Society
Volume144
Issue number31
DOIs
StatePublished - Aug 10 2022

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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