Syntheses of Isoxazoline-Based Amino Acids by Cycloaddition of Nitrile Oxides and Their Conversion into Highly Functionalized Bioactive Amino Acid Derivatives

Kiss, Loránd and Nonn, Melinda and Fülöp, Ferenc (2012) Syntheses of Isoxazoline-Based Amino Acids by Cycloaddition of Nitrile Oxides and Their Conversion into Highly Functionalized Bioactive Amino Acid Derivatives. Synthesis-Stuttgart, 44. pp. 1951-1963. ISSN 0039-7881

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Abstract

The present account illustrates the syntheses of isoxazoline- based amino acids by the cycloaddition of 1,3-dipolar nitrile oxides to the C–C double bond of unsaturated amino acid derivatives, with focus on the regio- and stereoselectivities of the transformations. Emphasis is also placed on the syntheses of highly functionalized amino acids by means of isoxazoline ring opening. The syntheses of various pharmacologically active compounds and their analogues via the above strategies are described.

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