Biologically interesting chiral 3,4-disubstituted pyrrolidines from optically active hydroxycitric acid lactones

被引:32
|
作者
Ibnusaud, I [1 ]
Thomas, G [1 ]
机构
[1] Mahatma Gandhi Univ, Sch Chem Sci, Kottayam 686560, Kerala, India
关键词
D O I
10.1016/S0040-4039(02)02781-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Starting with (2S,3S)-tetrahydro-3-hydroxy-5-oxo-2,3-furandicarboxylic acid (garcinia acid), isolated from the chiral pool, and alkyl amines, 3,4-disubstituted pyrrolidinediones, analogues of naturally occurring mescaline isocitrimidelactone, have been obtained in one-pot. These imides were subsequently converted into optically active pyrrolidines. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1247 / 1249
页数:3
相关论文
共 50 条
  • [1] Synthesis of Chiral 3,4-Disubstituted Pyrrolidines with Antibacterial Properties
    Rodriguez, Lenka
    Fisera, Roman
    Gaalova, Barbora
    Koci, Kamila
    Bujdakova, Helena
    Meciarova, Maria
    Gorova, Renata
    Jurdakova, Helena
    Sebesta, Radovan
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (17) : 2565 - 2575
  • [2] OPTICALLY PURE 3,4-DISUBSTITUTED AZETIDINONES FROM SUGARS
    CHMIELEWSKI, M
    KALUZA, Z
    ABRAMSKI, W
    GRODNER, J
    BELZECKI, C
    SEDMERA, P
    TETRAHEDRON, 1989, 45 (01) : 227 - 232
  • [3] Asymmetric synthesis of 3,4-disubstituted pyrrolidines: 1,3-dipolar addition to chiral bicyclic lactams
    Meyers, AI
    Fray, AH
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1997, 134 (3-4): : 283 - 298
  • [4] [3+2] CYCLOADDITION OF CHIRAL AZOMETHINE YLIDES FROM AMINOSUGAR N-OXIDES - ENANTIOSELECTIVE SYNTHESIS OF 3,4-DISUBSTITUTED PYRROLIDINES
    CHASTANET, J
    FATHALLAH, H
    NEGRON, G
    ROUSSI, G
    HETEROCYCLES, 1992, 34 (08) : 1565 - 1572
  • [5] CHIRAL SYNTHESIS OF 3,4-DISUBSTITUTED 2-AZETIDINONES FROM (R,R)-(+)-TARTARIC ACID
    GATEAUOLESKER, A
    CLEOPHAX, J
    GERO, SD
    TETRAHEDRON LETTERS, 1986, 27 (01) : 41 - 44
  • [6] Asymmetric synthesis of biologically useful 3,4-disubstitutedγ-lactone (3,4-Db)
    Cheong, CS
    Park, YJA
    Lee, SH
    Im, DS
    Jung, SH
    ENANTIOMER, 2000, 5 (06): : 585 - 590
  • [7] Ring transformation of 2-(haloalkyl)azetidines into 3,4-disubstituted pyrrolidines and piperidines
    Van Brabandt, W
    Van Landeghem, R
    De Kimpe, N
    ORGANIC LETTERS, 2006, 8 (06) : 1105 - 1108
  • [8] Synthesis of chiral 3,4-disubstituted pyrroles from L-amino acids
    Hover, JA
    Bock, CW
    Bhat, KL
    HETEROCYCLES, 2003, 60 (04) : 791 - 798
  • [9] CONDUCTING POLYMERS FROM 3,4-DISUBSTITUTED POLYPYRROLES
    RUHE, J
    KROHNKE, C
    EZQUERRA, TA
    KREMER, F
    WEGNER, G
    BERICHTE DER BUNSEN-GESELLSCHAFT-PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 1987, 91 (09): : 885 - 888
  • [10] NITROALKENE [4+2] CYCLOADDITION AS A GENERAL AND STEREOSELECTIVE ROUTE TO THE SYNTHESIS OF 3,3-DISUBSTITUTED AND 3,4-DISUBSTITUTED PYRROLIDINES
    DENMARK, SE
    MARCIN, LR
    JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (15): : 3857 - 3868