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 | |
| State | Published - Apr 26 2007 |
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ASJC Scopus subject areas
- Molecular Medicine
Cite this
Synthesis and stereochemical assignment of Brasilibactin A. / Mitchell, Judith M.; Shaw, Jared T.
In: Organic Letters, Vol. 9, No. 9, 26.04.2007, p. 1679-1681.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Synthesis and stereochemical assignment of Brasilibactin A
AU - Mitchell, Judith M.
AU - Shaw, Jared T.
PY - 2007/4/26
Y1 - 2007/4/26
N2 - 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.
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.
UR - http://www.scopus.com/inward/record.url?scp=34248332635&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=34248332635&partnerID=8YFLogxK
U2 - 10.1021/ol070355o
DO - 10.1021/ol070355o
M3 - Article
VL - 9
SP - 1679
EP - 1681
JO - Organic Letters
JF - Organic Letters
SN - 1523-7060
IS - 9
ER -