Selective Synthesis of Divergolide i

Daniel W. Terwilliger, Dirk Trauner

Research output: Contribution to journalArticle

Abstract

Divergolide I (1) is a naphthoquinone ansamycin that exhibits broad antibacterial activity. Its tetracyclic ring system is believed to be biosynthetically assembled via ring contraction of a macrocyclic precursor (proto-divergolide) that is both a macrolactone and a macrolactam. We here report a convergent and enantioselective synthesis that delivers the target molecule in less than 20 linear steps. Our work establishes the absolute configuration of divergolide I, confirms its relative configuration, and demonstrates that the biomimetic cyclization of a proto-divergolide can be surprisingly selective.

Original languageEnglish (US)
Pages (from-to)2748-2751
Number of pages4
JournalJournal of the American Chemical Society
Volume140
Issue number8
DOIs
StatePublished - Feb 28 2018

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Rifabutin
Naphthoquinones
Biomimetics
Cyclization
Molecules

ASJC Scopus subject areas

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

Cite this

Selective Synthesis of Divergolide i. / Terwilliger, Daniel W.; Trauner, Dirk.

In: Journal of the American Chemical Society, Vol. 140, No. 8, 28.02.2018, p. 2748-2751.

Research output: Contribution to journalArticle

Terwilliger, Daniel W. ; Trauner, Dirk. / Selective Synthesis of Divergolide i. In: Journal of the American Chemical Society. 2018 ; Vol. 140, No. 8. pp. 2748-2751.
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