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

共 50 条

[21] Synthesis of α,α-disubstituted amino acids based on tandem reaction of dehydroamino acid derivatives
Miyabe, H
Asada, R
Takemoto, Y
TETRAHEDRON, 2005, 61 (02) : 385 - 393
[22] Synthesis of highly functionalized amino acid and hydroxy acid derivatives from γ-aminoalkyl-substituted α-methylene-γ-butyrolactones
Steurer, S
Podlech, J
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (05) : 899 - 916
[23] SYNTHESIS OF DEHYDROAMINO ACIDS AND DIDEHYDRODIOXOPIPERAZINES AND THEIR CONVERSION INTO ALPHA-MERCAPTO-ALPHA-AMINO ACID-DERIVATIVES
HERSCHEID, JDM
SCHOLTEN, HPH
TIJHUIS, MW
OTTENHEIJM, HCJ
RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1981, 100 (02): : 73 - 78
[24] AMINO-ACIDS AND PEPTIDES .8. SYNTHESES OF N'-AMINOACID DERIVATIVES OF HYDRAZIDE OF ISONICOTINIC-ACID
AGADZHANYAN, TE
MATANYAN, AA
ARMYANSKII KHIMICHESKII ZHURNAL, 1974, 27 (09): : 785 - 789
[25] AMINO-ACIDS .12. SYNTHESES OF DL-CYSTEINES FROM ACRYLIC-ACID DERIVATIVES
EFFENBERGER, F
BEISSWENGER, T
DANNENHAUER, F
CHEMISCHE BERICHTE-RECUEIL, 1988, 121 (12): : 2209 - 2223
[26] STUDIES ON HYDROXY AMINO-ACIDS .4. SYNTHESES OF SEVERAL PEPTIDES CONTAINING AZIRIDINECARBOXYLIC ACID DERIVED FROM CORRESPONDING HYDROXY AMINO-ACID DERIVATIVES
NAKAGAWA, Y
NAKAJIMA, K
OKAWA, K
TSUNO, T
IWAI, M
KAWAI, H
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1972, 45 (04) : 1162 - +
[27] ASYMMETRIC SYNTHESES OF 1-AMINO-2-PHENYL(ALKYL)CYCLOPROPANECARBOXYLIC ACIDS BY DIASTEREOSELECTIVE CYCLOPROPANATION OF HIGHLY FUNCTIONALIZED MONOCHIRAL OLEFINS
ALCARAZ, C
FERNANDEZ, MD
DEFRUTOS, MP
MARCO, JL
BERNABE, M
TETRAHEDRON, 1994, 50 (43) : 12443 - 12456
[28] Highly diastereoselective entry to chiral oxindole-based β-amino boronic acids and spiro derivatives
Manenti, Marco
Gazzotti, Stefano
Lo Presti, Leonardo
Molteni, Giorgio
Silvani, Alessandra
ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (33) : 7211 - 7216
[29] Monoterpene-based chiral β-amino acid derivatives prepared from natural sources: syntheses and applications
Zsolt Szakonyi
Ferenc Fülöp
Amino Acids, 2011, 41 : 597 - 608
[30] Monoterpene-based chiral β-amino acid derivatives prepared from natural sources: syntheses and applications
Szakonyi, Zsolt
Fueloep, Ferenc
AMINO ACIDS, 2011, 41 (03) : 597 - 608

← 1 2 3 4 5 →