Synthesis of [c]-Fused Bicyclic Proline Analogues

被引:10
|
作者
Isabel Calaza, M. [1 ]
Sayago, Francisco J. [1 ]
Laborda, Pedro [1 ]
Cativiela, Carlos [1 ]
机构
[1] Univ Zaragoza, CSIC, ISQCH, Dept Quim Organ, E-50009 Zaragoza, Spain
关键词
Amino acids; Nitrogen heterocycles; Proline analogues; Diastereoselectivity; Enantioselectivity; HEPATITIS-C VIRUS; HIGHLY STEREOSELECTIVE-SYNTHESIS; TETRAPEPTIDYL ALPHA-KETOAMIDES; CENTERED GLYCINE RADICALS; PAUSON-KHAND REACTION; X=Y-ZH SYSTEMS; ASYMMETRIC-SYNTHESIS; AMINO-ACID; 1,3-DIPOLAR CYCLOADDITION; DIASTEREOSELECTIVE SYNTHESIS;
D O I
10.1002/ejoc.201403121
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An overview of synthetic methods developed to build [c]-fused bicyclic proline analogues is presented. The focus is on the preparation of azabicycles that bear a carbocyclic ring fused to the [c] face of the pyrrolidine unit. Attention is paid both to procedures that afford the desired compounds in racemic form and to asymmetric strategies. Procedures are organized according to the size of the carbocycle that is fused to the pyrrolidine moiety. Strategies able to provide multigram quantities of enantiopure compounds that have application in the synthesis of marketed drugs are highlighted.
引用
收藏
页码:1633 / 1658
页数:26
相关论文
共 50 条
  • [41] Synthesis of bicyclic systems containing fused sulfolane and isoxazolidine rings
    Valentina M. Berestovitskaya
    Irina E. Efremova
    Anna V. Serebryannikova
    Lidiya V. Lapshina
    Vladislav V. Gurzhiy
    Chemistry of Heterocyclic Compounds, 2018, 54 : 76 - 82
  • [42] Synthesis of bicyclic systems containing fused sulfolane and isoxazolidine rings
    Berestovitskaya, Valentina M.
    Efremova, Irina E.
    Serebryannikova, Anna V.
    Lapshina, Lidiya V.
    Gurzhiy, Vladislav V.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2018, 54 (01) : 76 - 82
  • [43] Synthesis of Chlorinated Bicyclic C-Fused Tetrahydrofuro[3,2-c] azetidin-2-ones
    Ram, Ram N.
    Kumar, Neeraj
    Singh, Nem
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (21): : 7408 - 7411
  • [44] Synthesis of Fused and Bridged Bicyclic Diazenium Salts by Intramolecular Cycloaddition
    Javed, Muhammad I.
    Wyman, Jodi M.
    Brewer, Matthias
    ORGANIC LETTERS, 2009, 11 (10) : 2189 - 2192
  • [45] SYNTHESIS OF BICYCLIC FUSED CARBOCYCLES VIA INTRAMOLECULAR DEHYDRATIVE ALKYLATION
    YU, JR
    CHO, HS
    FALCK, JR
    TETRAHEDRON LETTERS, 1995, 36 (47) : 8577 - 8580
  • [46] Synthesis and Antiplasmodial Activity of Bicyclic Dioxanes as Simplified Dihydroplakortin Analogues
    Gemma, Sandra
    Kunjir, Sanil
    Coccone, Salvatore Sanna
    Brindisi, Margherita
    Moretti, Vittoria
    Brogi, Simone
    Novellino, Ettore
    Basilico, Nicoletta
    Parapini, Silvia
    Taramelli, Donatella
    Campiani, Giuseppe
    Butini, Stefania
    JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (16) : 5949 - 5953
  • [47] Photochemical Synthesis of Nucleoside Analogues from Cyclobutanones: Bicyclic and Isonucleosides
    Jaffer, Mileina
    Ebead, Abdelaziz
    Lee-Ruff, Edward
    MOLECULES, 2010, 15 (06): : 3816 - 3828
  • [48] Iminosugar C-Nitromethyl Glycoside: Stereoselective Synthesis of Isoxazoline and Isoxazole-Fused Bicyclic Iminosugars
    Prasad, Sure Siva
    Baskaran, Sundarababu
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (03): : 1558 - 1564
  • [49] Conformational Preference of Fused Carbohydrate-Templated Proline Analogues-A Computational Study
    Teklebrhan, Robel B.
    Owens, Neil W.
    Xidos, James D.
    Schreckenbach, Georg
    Wetmore, Stacey D.
    Schweizer, Frank
    JOURNAL OF PHYSICAL CHEMISTRY B, 2013, 117 (01): : 199 - 205
  • [50] Synthesis and Insecticidal Evaluation of Neonicotinoid Analogues with Bicyclic Ring System
    Chen, Yinbo
    Fan, Jie
    Xia, Shuang
    Cheng, Jiagao
    Xu, Xiaoyong
    Li, Zhong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (02) : 409 - 413