A REDUCTIVE ALDOL STRATEGY FOR THE SYNTHESIS OF VERY HIGHLY SUBSTITUTED CYCLOPENTANES FROM SUGAR LACTONES

被引:15
作者
ELLIOTT, RP
FLEET, GWJ
PEARCE, L
SMITH, C
WATKIN, DJ
机构
[1] UNIV OXFORD,DYSON PERRINS LAB,S PARKS RD,OXFORD OX1 3QY,ENGLAND
[2] GLAXO GRP RES LTD,GREENFORD UB6 0HE,MIDDX,ENGLAND
[3] UNIV OXFORD,CRYSTALLOG LAB,OXFORD OX1 3PD,ENGLAND
关键词
D O I
10.1016/0040-4039(91)80795-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Iodide ion induces a protected 5-formyl-2-iodo-1,5-lactone to undergo a reductive aldol condensation to give a fully substituted cyclopentane derivative in moderate yield; this strategy may provide a general synthesis of such highly functionalised carbocycles as mannostatins and allosamizolines.
引用
收藏
页码:6227 / 6230
页数:4
相关论文
共 21 条
  • [11] FERRIER RJ, 1984, J CHEM SOC PERK T 1, P1689
  • [12] FLEET GWJ, 1990, CARBOHYD RES, V202, P105
  • [13] FLEET GWJ, 1990, TETRAHEDRON, V46, P19
  • [14] STRUCTURE DETERMINATION OF MANNOSTATIN-A AND MANNOSTATIN-B
    MORISHIMA, H
    KOJIRI, K
    YAMAMOTO, T
    AOYAGI, T
    NAKAMURA, H
    IITAKA, Y
    [J]. JOURNAL OF ANTIBIOTICS, 1989, 42 (06) : 1008 - 1011
  • [15] MYERSCOUGH P, UNPUB
  • [16] SAKUDA S, 1987, AGR BIOL CHEM TOKYO, V51, P3251
  • [17] SAKUDA S, 1988, AGR BIOL CHEM TOKYO, V52, P1615
  • [18] THE STRUCTURE OF ALLOSAMIDIN, A NOVEL INSECT CHITINASE INHIBITOR, PRODUCED BY STREPTOMYCES SP
    SAKUDA, S
    ISOGAI, A
    MATSUMOTO, S
    SUZUKI, A
    KOSEKI, K
    [J]. TETRAHEDRON LETTERS, 1986, 27 (22) : 2475 - 2478
  • [19] MANNOSTATIN-A, A NEW GLYCOPROTEIN-PROCESSING INHIBITOR
    TROPEA, JE
    KAUSHAL, GP
    PASTUSZAK, I
    MITCHELL, M
    AOYAGI, T
    MOLYNEUX, RJ
    ELBEIN, AD
    [J]. BIOCHEMISTRY, 1990, 29 (43) : 10062 - 10069
  • [20] TEMPLATE-DIRECTED SYNTHESIS OF (+/-)-ALLOSAMIZOLINE AND ITS 3,4-EPIMERS
    TROST, BM
    VANVRANKEN, DL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (03) : 1261 - 1263