Synthesis and stereochemical assignment of Brasilibactin A

Judith M. Mitchell; Jared T. Shaw

doi:10.1021/ol070355o

Synthesis and stereochemical assignment of Brasilibactin A

Judith M. Mitchell, Jared T. Shaw

Chemistry

Research output: Contribution to journal › Article › peer-review

22 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 language	English (US)
Pages (from-to)	1679-1681
Number of pages	3
Journal	Organic Letters
Volume	9
Issue number	9
DOIs	https://doi.org/10.1021/ol070355o
State	Published - Apr 26 2007

ASJC Scopus subject areas

Molecular Medicine

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AB - 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.

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Synthesis and stereochemical assignment of Brasilibactin A

Abstract

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