SYNTHESIS OF CYCLOPENTANE SPIROHYDANTOINS BY ALDOL CYCLIZATIONS - AN APPROACH TO HIGHLY SUBSTITUTED ALPHA-CYCLOPENTANE AMINO-ACIDS

被引:12
作者
FAIRBANKS, AJ
ELLIOTT, RP
SMITH, C
HUI, A
WAY, G
STORER, R
TAYLOR, H
WATKIN, DJ
WINCHESTER, BG
FLEET, GWJ
机构
[1] OXFORD CTR MOLEC SCI,DYSON PERKINS LAB,OXFORD OX1 3QY,OXON,ENGLAND
[2] UNIV OXFORD,CHEM CRYSTALLOG LAB,OXFORD OX1 3PD,OXON,ENGLAND
[3] UNIV LONDON,INST CHILD HLTH,LONDON WC1N 1EH,ENGLAND
[4] GLAXO GRP RES LTD,GREENFORD UB6 0HE,MIDDX,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)61521-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Efficient but reversible aldol condensations of 2-azido-5-formyl-1,5-lactones provide short routes to precursors for alpha-cyclopentane amino acids, some aminopseudosugars and spirohydantoins of cyclopentanes with control of the stereochemistry at all 5 carbons bearing functional groups. The effects of some of the compounds on human liver glycosidases are described.
引用
收藏
页码:7953 / 7956
页数:4
相关论文
共 8 条
  • [1] IMINOHEPTITOLS AS GLYCOSIDASE INHIBITORS - SYNTHESIS OF ALPHA-HOMOMANNOJIRIMYCIN, 6-EPI-ALPHA-HOMOMANNOJIRIMYCIN AND OF A HIGHLY SUBSTITUTED PIPECOLIC ACID
    BRUCE, I
    FLEET, GWJ
    DIBELLO, IC
    WINCHESTER, B
    [J]. TETRAHEDRON, 1992, 48 (46) : 10191 - 10200
  • [2] ANOMERIC SPIROHYDANTOINS OF MANNOFURANOSE - APPROACHES TO NOVEL ANOMERIC AMINO-ACIDS BY AN OXIDATIVE RING CONTRACTION
    BURTON, JW
    SON, JC
    FAIRBANKS, AJ
    CHOI, SMS
    TAYLOR, H
    WATKIN, DJ
    WINCHESTER, BG
    FLEET, GWJ
    [J]. TETRAHEDRON LETTERS, 1993, 34 (38) : 6119 - 6122
  • [3] THE SYNTHESIS OF PSEUDO-SUGARS RELATED TO ALLOSAMIZOLINE
    CORBETT, DF
    DEAN, DK
    ROBINSON, SR
    [J]. TETRAHEDRON LETTERS, 1993, 34 (09) : 1525 - 1528
  • [4] DIBELLO IC, 1989, BIOCHEM J, V159, P855
  • [5] SYNTHESIS OF 1-EPIHYDANTOCIDIN FROM D-RIBOSE
    FAIRBANKS, AJ
    FORD, PS
    WATKIN, DJ
    FLEET, GWJ
    [J]. TETRAHEDRON LETTERS, 1993, 34 (20) : 3327 - 3330
  • [6] FLEET GWJ, 1990, TETRAHEDRON, V46, P19
  • [7] SKEAD BM, 1993, TETRAHEDRON LETT, V34, P615
  • [8] TROST BM, 1993, J AM CHEM SOC, V115, P4458