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

被引：35

作者：

Kiss, Lorand ^{[1
]}

Nonn, Melinda ^{[1
,2
]}

Fueloep, Ferenc ^{[1
,2
]}

机构：

[1] Univ Szeged, Inst Pharmaceut Chem, H-6720 Szeged, Hungary

[2] Univ Szeged, Hungarian Acad Sci, Stereochem Res Grp, H-6720 Szeged, Hungary

来源：

SYNTHESIS-STUTTGART | 2012年 / 44卷 / 13期

关键词：

amino acids; amino alcohols; cycloaddition; diastereo-selectivity; heterocycles; ring opening; stereoselective synthesis; 1,3-DIPOLAR CYCLOADDITION; NEURAMINIDASE INHIBITORS; CYCLOPENTANE DERIVATIVES; REDUCTION; NUCLEOSIDES; DISCOVERY; OXIDATION; HOMOLOGS;

D O I：

10.1055/s-0031-1290373

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：1951 / 1963

页数：13

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