An efficient route to all eight stereoisomers of a tri-functionalised cyclopentane scaffold for drug discovery

被引:21
作者
Smith, MEB [1 ]
Lloyd, MC [1 ]
Derrien, N [1 ]
Lloyd, RC [1 ]
Taylor, SJC [1 ]
Chaplin, DA [1 ]
Casy, G [1 ]
McCague, R [1 ]
机构
[1] Ascot Fine Chem, ChiroTech, Cambridge CB4 0WG, England
关键词
D O I
10.1016/S0957-4166(01)00108-2
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A route to all eight stereoisomers of 3-(tert-butoxycarbonylamino)-4-hydroxycyclopentanecarboxylic acid methyl ester is presented; these products should prove to be valuable scaffolds in pharmaceutical discovery. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:703 / 705
页数:3
相关论文
共 7 条
  • [1] IMPROVED PROCEDURES FOR THE PREPARATION OF (+)-(1R,2S,4R)-4-AMINO-2-HYDROXY-1-HYDROXYMETHYL CYCLOPENTANE
    BRAY, BL
    DOLAN, SC
    HALTER, B
    LACKEY, JW
    SCHILLING, MB
    TAPOLCZAY, DJ
    [J]. TETRAHEDRON LETTERS, 1995, 36 (25) : 4483 - 4486
  • [2] ROLE OF SIGMA-DONATION IN THE STEREOCONTROL OF HYDROGEN-TRANSFER REACTIONS INVOLVING ACYCLIC RADICALS
    GUINDON, Y
    SLASSI, A
    RANCOURT, J
    BANTLE, G
    BENCHEQROUN, M
    MURTAGH, L
    GHIRO, E
    JUNG, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (02) : 288 - 289
  • [3] MCCAGUE R, 2000, MODERN DRUG DISC JUL, P29
  • [4] Qui J., 2000, J MED CHEM, V43, P706
  • [5] Highly selective directed hydrogenation of enantiopure 4-(tert-butoxycarbonylamino)cyclopent-1-enecarboxylic acid methyl esters
    Smith, MEB
    Derrien, N
    Lloyd, MC
    Taylor, SJC
    Chaplin, DA
    McCague, R
    [J]. TETRAHEDRON LETTERS, 2001, 42 (07) : 1347 - 1350
  • [6] DEVELOPMENT OF THE BIOCATALYTIC RESOLUTION OF 2-AZABICYCLO[2.2.1]HEPT-5-EN-3-ONE AS AN ENTRY TO SINGLE-ENANTIOMER CARBOCYCLIC NUCLEOSIDES
    TAYLOR, SJC
    MCCAGUE, R
    WISDOM, R
    LEE, C
    DICKSON, K
    RUECROFT, G
    OBRIEN, F
    LITTLECHILD, J
    BEVAN, J
    ROBERTS, SM
    EVANS, CT
    [J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (06) : 1117 - 1128
  • [7] CHEMOENZYMATIC SYNTHESIS OF (-)-CARBOVIR UTILIZING A WHOLE CELL CATALYZED RESOLUTION OF 2-AZABICYCLO[2.2.1]HEPT-5-EN-3-ONE
    TAYLOR, SJC
    SUTHERLAND, AG
    LEE, C
    WISDOM, R
    THOMAS, S
    ROBERTS, SM
    EVANS, C
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (16) : 1120 - 1121