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. 2007 May 25;72(11):4055-66.
doi: 10.1021/jo062588j. Epub 2007 Apr 28.

Investigation of the regioselectivity for the staudinger reaction and its application for the synthesis of aminoglycosides with N-1 modification

Jie Li  1 , Fang-I Chiang, Hsiao-Nung Chen, Cheng-Wei Tom Chang
Affiliations

Investigation of the regioselectivity for the staudinger reaction and its application for the synthesis of aminoglycosides with N-1 modification

Jie Li et al. J Org Chem. .

Abstract

The criteria for controlling the regioselectivity of Staudinger reduction of azides have been investigated. These findings enable a convenient direct N-1 modification of the perazidoneamine and perazidoribostamycin resulting in the synthesis of aminoglycoside antibiotics with activity against drug-resistant bacteria.

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Figures

Figure 1
Figure 1. Structures of Neomycin Class Aminoglycosides
Figure 2
Figure 2. Numbering System for Neomycin and Kanamycin Classes Aminoglycosides
Figure 3
Figure 3. Structures of JL040 and Gentamicin
Scheme 1
Scheme 1. Strategy for Regioselective Reduction of Azido Group
Scheme 2
Scheme 2. Reported Regioselective Reduction of Azido Group
Scheme 3
Scheme 3. Synthesis of Azidoneamine Derivatives
Scheme 4
Scheme 4. Regioselective Staudinger Reduction of Azidoneamine Derivatives
Scheme 5
Scheme 5. Staudinger Reduction of Compound 4
Scheme 6
Scheme 6. Regioselective Staudinger Reduction of Azidoneomycin
Scheme 7
Scheme 7. Regioselective Staudinger Reduction of Azidoribostamycin
Scheme 8
Scheme 8. Synthesis of Kanamycin Class Aminoglycosides with N-1 AHB
Scheme 8
Scheme 8. Synthesis of Kanamycin Class Aminoglycosides with N-1 AHB
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References

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    1. Hanessian S, Haskell TH. In: Antibiotics Containing Sugars. Pigmann H, Horton D, editors. Academic Press; New York/Lodon: 1970. pp. 139–211.
    1. Haddad J, Kotra LP, Mobashery S. In: Glycochemistry Principles, Synthesis, and Applications. Wang PG, Bertozzi CR, editors. Marcel Dekker, Inc; New York/Basel: 2001. pp. 307–424.
    1. Hanessian S, Kornienko A, Swayze EE. Tetrahedron. 2003;59:995–1007.
    1. Tsuchiya T, Takagi Y, Umezawa S. Tetrahedron Lett. 1979;51:4951–4954.

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