Recent Advances in Application of Amino Acids: Key Building Blocks in Design and Syntheses of Heterocyclic Compounds

被引:74
作者
Heravi, Majid M. [1 ]
Vavsari, Vaezeh Fathi [1 ]
机构
[1] Alzahra Univ, Sch Sci, Dept Chem, Tehran, Iran
来源
ADVANCES IN HETEROCYCLIC CHEMISTRY, VOL 114 | 2015年 / 114卷
关键词
Amino acids; Asymmetric synthesis; Bifunctional; Chiral catalyst; Heterocyclization; Natural products; SOLID-PHASE SYNTHESIS; ENANTIOSELECTIVE TOTAL-SYNTHESIS; COMBINATORIAL ORGANIC-SYNTHESIS; PICTET-SPENGLER REACTION; INTRAMOLECULAR ENYNE METATHESIS; 1,3-DIPOLAR CYCLOADDITION; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; FLUOROUS SYNTHESIS; PEPTIDE-SYNTHESIS;
D O I
10.1016/bs.aihch.2015.02.002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Amino acids (AAs) are usually considered as important scaffolds for peptides and proteins. However, in the past decades, they have been extensively used as important synthons for the syntheses of a variety of heterocyclic systems, especially for those in which one particular stereoisomer should be obtained via asymmetric synthesis. Although the applications of AAs as synthons in heterocyclization were extensively reviewed in 1995, numerous recent reports concerning their use for the construction of a wide variety of differently sized heterocycles make the subject worthwhile of update.
引用
收藏
页码:77 / 145
页数:69
相关论文
共 255 条
[1]   New chiral alanine template with a 1,2,3,6-tetrahydro-2-pyrazinone structure for the asymmetric synthesis of α-methyl α-amino acids [J].
Abellán, T ;
Nájera, C ;
Sansano, JM .
TETRAHEDRON-ASYMMETRY, 1998, 9 (13) :2211-2214
[2]   Heterocyclic nucleoside analogues by cycloaddition reactions of 1-vinylthymine with 1,3-dipoles [J].
Adams, DR ;
Boyd, ASF ;
Ferguson, R ;
Grierson, DS ;
Monneret, C .
NUCLEOSIDES & NUCLEOTIDES, 1998, 17 (06) :1053-1075
[3]   A concise asymmetric route to the bridged bicyclic tropane alkaloid ferruginine using enyne ring-closing metathesis [J].
Aggarwal, VK ;
Astle, CJ ;
Rogers-Evans, M .
ORGANIC LETTERS, 2004, 6 (09) :1469-1471
[4]   Asymmetric synthesis of N-aryl aziridines [J].
Aires-de-Sousa, J ;
Prabhakar, S ;
Lobo, AM ;
Rosa, AM ;
Gomes, MJS ;
Corvo, MC ;
Williams, DJ ;
White, AJP .
TETRAHEDRON-ASYMMETRY, 2002, 12 (24) :3349-3365
[5]   Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 15. Generation of alkoxycarbonyl(sulfenyl)carbenes and their intramolecular insertion to give alkenyl sulfides [J].
Aitken, RA ;
Armstrong, JM ;
Drysdale, MJ ;
Ross, FC ;
Ryan, BM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (05) :593-604
[6]   Asymmetric synthesis of 1-(2-pyrrolyl)alkylamines by the addition of organometallic reagents to chiral 2-pyrroleimines [J].
Alvaro, Giuseppe ;
Di Fabio, Romano ;
Gualandi, Andrea ;
Savoia, Diego .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (33) :5573-5582
[7]   Pulchellalactam:: A CD45 protein tyrosine phosphatase inhibitor from the marine fungus Corollospora pulchella [J].
Alvi, KA ;
Casey, A ;
Nair, BG .
JOURNAL OF ANTIBIOTICS, 1998, 51 (05) :515-517
[8]  
[Anonymous], TARGETS IN HETEROCYC
[9]   HIGHLY STEREOCONTROLLED TOTAL SYNTHESIS OF (+)-ALLOPUMILIOTOXIN-339A [J].
AOYAGI, S ;
WANG, TC ;
KIBAYASHI, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) :10653-10654
[10]   HIGHLY STEREOSELECTIVE TOTAL SYNTHESES OF (+)-ALLOPUMILIOTOXIN-267A AND (+)-ALLOPUMILIOTOXIN-339A VIA INTRAMOLECULAR NICKEL(II) CHROMIUM(II)-MEDIATED CYCLIZATION [J].
AOYAGI, S ;
WANG, TC ;
KIBAYASHI, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (24) :11393-11409