1,3-Dipolar Cycloadditions in the Synthesis of Carbohydrate Mimics. Part 1: Nitrile Oxides and Nitronates

Author(s): J. K. Gallos, A. E. Koumbis.

Journal Name: Current Organic Chemistry

Volume 7 , Issue 5 , 2003

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Abstract:

This article (the first of three parts) reviews the use of 1,3-dipolar cycloaddition reactions of nitrile oxides and nitronates in the construction of carbohydrate mimics. Preparation of isoxazolidine and other modified nucleosides, isoxazolidine fused systems, C-disaccharides, polyhydroxylated and aminopolyhydroxylated carbocycles and azasugars, amino sugars, polyhydroxylated alkaloids of the pyrrolidine and indolizidine series is described. It is organized depending on the dipole employed and subdivided into separate sections according to the inter- or intramolecular fashion applied and the nature of dipolarophiles and dipoles incorporated. It is mainly dedicated to the synthetic preparations and stereoselectivities observed with limited reports to biological tests and results.

Keywords: dipolar cycloadditions, carbohydrate mimics, nitrice oxides, nitronates

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Article Details

VOLUME: 7
ISSUE: 5
Year: 2003
Page: [397 - 426]
Pages: 30
DOI: 10.2174/1385272033372734
Price: $58

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