A surprising dipolar cycloaddition provides ready access to aminoglycosides

Journal of the American Chemical Society

Volumn 126, Issue 27, 2004, Pages 8356-8357

  Dahl, Russell S ^a   Finney, Nathaniel S ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOGLYCOSIDE; AZIRIDINE DERIVATIVE; CARBOHYDRATE; NITROGEN; TRIAZOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIPOLE; PHOTOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; STOICHIOMETRY; SYNTHESIS;

AMINOGLYCOSIDES; CYCLIZATION; DEOXYGLUCOSE; TRIAZOLES;

EID: 3142738147     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0319238     Document Type: Article

References (43)

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32. While we have encountered no problems in this respect, CAUTION should always be used when heating solutions of azides.
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38. 1H NMR spectra.
39. C2 configurations were assigned based on X-ray crystallographic analysis of 4b. The C1 configuration was assigned based on 1H coupling constants.
40. Formation of the acetone adduct could also proceed through O-alkylation of acetone followed by rearrangement. We thank Prof. C. Rojas (Barnard College) for bringing this possibility to our attention. See: Zhang, Y.; Reynolds, N. T.; Manju, K.; Rovis, T. J. Am. Chem. Soc. 2002, 124, 9720.
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43. Loss of the TBS group during the cycloaddition accounts for the majority of material loss. Optimization is currently under way in the context of identifying an appropriate silyl linker for solid-phase synthesis.