A surprising dipolar cycloaddition provides ready access to aminoglycosides

Journal of the American Chemical Society
Russell S Dahl, Nathaniel S Finney

Abstract

This contribution describes the results of a new research effort in our laboratory aimed at the synthesis of novel aminoglycosides and amino-C-glycosides. Despite the importance of such compounds, and the previous development of some methodological solutions, this remains an important area of research. Notable features of our approach, which is distinct from and complementary to previous efforts, are the following: (1) Reliance on a surprising and unprecedented formation of glycal triazolines via an inverse electron demand dipolar cycloaddition of glucal. We believe this desirable transformation has not previously been discovered because of the unusual selection of substrates and solvent required. (2) Very mild reaction conditions. An initial thermal cycloaddition is carried out in an inert solvent, the triazoline generated is photochemically converted to a reactive aziridine, and the crude aziridine undergoes ring opening at room temperature in the presence of a nucleophile and a mild Lewis acid catalyst. (3) Formation of products lacking an N-acyl group, allowing ready synthesis of novel glucosamine derivatives.

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Citations

Jan 27, 2007·The Journal of Organic Chemistry·Aileen F G BongatAlexei V Demchenko
Jul 26, 2008·Chemical Communications : Chem Comm·Alexander AdibekianPeter H Seeberger
Dec 6, 2008·Chemical Communications : Chem Comm·Divya Agrawal, Veejendra K Yadav
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Aug 16, 2005·Angewandte Chemie·Stefan BräseViktor Zimmermann
Feb 10, 2021·Organic Letters·Wenbin ShangChengfeng Xia
Jan 27, 2012·Macromolecules·José A CastilloMarcus Weck
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Nov 25, 2005·Journal of the American Chemical Society·Veejendra K Yadav, Vardhineedi Sriramurthy
Feb 22, 2011·Carbohydrate Research·François-Moana GautierCyrille Grandjean

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Aminoglycosides (ASM)

Aminoglycoside is a medicinal and bacteriologic category of traditional Gram-negative antibacterial medications that inhibit protein synthesis and contain as a portion of the molecule an amino-modified glycoside. Discover the latest research on aminoglycoside here.

Aminoglycosides

Aminoglycoside is a medicinal and bacteriologic category of traditional Gram-negative antibacterial medications that inhibit protein synthesis and contain as a portion of the molecule an amino-modified glycoside. Discover the latest research on aminoglycoside here.