Synthesis and stereochemical assignment of Brasilibactin A

Judith M. Mitchell, Jared T. Shaw

Research output: Contribution to journalArticle

21 Scopus citations

Abstract

Brasilibactin A, a naturally occurring siderophore related to the mycobactins, has been synthesized in six steps. Use of asymmetric titanium-mediated aldol reactions allowed the preparation of both diastereomers from a common synthetic intermediate, thus allowing the relative stereochemistry of the natural product to be assigned. Brasilibactin A exhibits no inhibition of histone deacetylases (HDACs) in spite of the N-formyl-N-hydroxy lysine moiety that is expected to affect the activity of these metal-dependent lysine-modifying enzymes.

Original languageEnglish (US)
Pages (from-to)1679-1681
Number of pages3
JournalOrganic Letters
Volume9
Issue number9
DOIs
StatePublished - Apr 26 2007

ASJC Scopus subject areas

  • Molecular Medicine

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