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Synthesis of brasilibactin A and confirmation of absolute configuration of β-hydroxy acid fragment

Publication ,  Journal Article
Ying, Y; Hong, J
Published in: Tetrahedron Letters
November 12, 2007

A synthesis of brasilibactin A, a cytotoxic siderophore from the actinomycete of Nocardia brasiliensis, and three unnatural diastereomers of the natural product is described. Four possible diastereomers of the β-hydroxy acid fragment were prepared via asymmetric aldol reactions and used to synthesize brasilibactin A and its diastereomers. Careful analysis of 1H NMR data confirmed that brasilibactin A possesses the 17S,18R absolute stereochemistry. © 2007 Elsevier Ltd. All rights reserved.

Duke Scholars

Published In

Tetrahedron Letters

DOI

ISSN

0040-4039

Publication Date

November 12, 2007

Volume

48

Issue

46

Start / End Page

8104 / 8107

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 3101 Biochemistry and cell biology
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry
 

Citation

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Ying, Y., & Hong, J. (2007). Synthesis of brasilibactin A and confirmation of absolute configuration of β-hydroxy acid fragment. Tetrahedron Letters, 48(46), 8104–8107. https://doi.org/10.1016/j.tetlet.2007.09.112
Ying, Y., and J. Hong. “Synthesis of brasilibactin A and confirmation of absolute configuration of β-hydroxy acid fragment.” Tetrahedron Letters 48, no. 46 (November 12, 2007): 8104–7. https://doi.org/10.1016/j.tetlet.2007.09.112.
Ying Y, Hong J. Synthesis of brasilibactin A and confirmation of absolute configuration of β-hydroxy acid fragment. Tetrahedron Letters. 2007 Nov 12;48(46):8104–7.
Ying, Y., and J. Hong. “Synthesis of brasilibactin A and confirmation of absolute configuration of β-hydroxy acid fragment.” Tetrahedron Letters, vol. 48, no. 46, Nov. 2007, pp. 8104–07. Scopus, doi:10.1016/j.tetlet.2007.09.112.
Ying Y, Hong J. Synthesis of brasilibactin A and confirmation of absolute configuration of β-hydroxy acid fragment. Tetrahedron Letters. 2007 Nov 12;48(46):8104–8107.
Journal cover image

Published In

Tetrahedron Letters

DOI

ISSN

0040-4039

Publication Date

November 12, 2007

Volume

48

Issue

46

Start / End Page

8104 / 8107

Related Subject Headings

  • Organic Chemistry
  • 3405 Organic chemistry
  • 3404 Medicinal and biomolecular chemistry
  • 3101 Biochemistry and cell biology
  • 0305 Organic Chemistry
  • 0304 Medicinal and Biomolecular Chemistry