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
Current Organic Chemistry
Title: 1,3-Dipolar Cycloadditions in the Synthesis of Carbohydrate Mimics. Part 1: Nitrile Oxides and Nitronates
Volume: 7 Issue: 5
Author(s): J. K. Gallos and A. E. Koumbis
Affiliation:
Keywords: dipolar cycloadditions, carbohydrate mimics, nitrice oxides, nitronates
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.
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Cite this article as:
Gallos K. J. and Koumbis E. A., 1,3-Dipolar Cycloadditions in the Synthesis of Carbohydrate Mimics. Part 1: Nitrile Oxides and Nitronates, Current Organic Chemistry 2003; 7 (5) . https://dx.doi.org/10.2174/1385272033372734
DOI https://dx.doi.org/10.2174/1385272033372734 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Chemistry and Biology of Carbohydrates
Carbohydrates are one of the most abundant natural products and are considered to be extremely important biomolecules for their ever-increasing impact on chemistry and biology. Their role in several important biological processes, notably energy storage, transport, modulation of protein function, intercellular adhesion, malignant transformation, signal transduction, viral, and bacterial cell ...read more
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