STEREOSTRUCTURAL STUDIES ON THE 4-HYDROXYLATED ANNONACEOUS ACETOGENINS - SYNTHESIS OF MODEL BUTENOLIDES OF KNOWN RELATIVE AND ABSOLUTE-CONFIGURATION INVOLVING AN INTRIGUING TRANSLACTONIZATION REACTION

被引:14
作者
HOYE, TR
HANSON, PR
HASENWINKEL, LE
RAMIREZ, EA
ZHUANG, ZP
机构
[1] Department of Chemistry, University of Minnesota, Minneapolis
关键词
D O I
10.1016/S0040-4039(00)78427-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Each diastereomer of model butenolides 3 was synthesized from appropriate antipodes of two propylene oxide molecules. Concomitant translactonization reactions have important stereochemical ramifications.
引用
收藏
页码:8525 / 8528
页数:4
相关论文
共 10 条
  • [1] ANNONACEOUS ACETOGENINS - AN UPDATED REVIEW
    FANG, XP
    RIESER, MJ
    GU, ZM
    ZHAO, GX
    MCLAUGHLIN, JL
    [J]. PHYTOCHEMICAL ANALYSIS, 1993, 4 (01) : 27 - 48
  • [2] SYNTHESIS OF (-)-BULLATACIN - THE ENANTIOMER OF A POTENT, ANTITUMOR, 4-HYDROXYLATED, ANNONACEOUS ACETOGENIN
    HOYE, TR
    HANSON, PR
    [J]. TETRAHEDRON LETTERS, 1993, 34 (32) : 5043 - 5046
  • [3] HOYE TR, IN PRESS TETRAHEDRON
  • [4] BULLATACIN AND BULLATACINONE - 2 HIGHLY POTENT BIOACTIVE ACETOGENINS FROM ANNONA-BULLATA
    HUI, YH
    RUPPRECHT, JK
    LIU, YM
    ANDERSON, JE
    SMITH, DL
    CHANG, CJ
    MCLAUGHLIN, JL
    [J]. JOURNAL OF NATURAL PRODUCTS, 1989, 52 (03): : 463 - 477
  • [5] NEW METHOD FOR SYNTHESIS OF VARIOUS TYPES OF SUBSTITUTED 2(5H)-FURANONES
    IWAI, K
    KOSUGI, H
    UDA, H
    KAWAI, M
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (01) : 242 - 247
  • [6] TOTAL SYNTHESIS OF (+)-ROLLINIASTATIN-1
    KOERT, U
    [J]. TETRAHEDRON LETTERS, 1994, 35 (16) : 2517 - 2520
  • [7] DETERMINATION OF ABSOLUTE-CONFIGURATION OF STEREOGENIC CARBINOL CENTERS IN ANNONACEOUS ACETOGENINS BY H-1-NMR AND F-19-NMR ANALYSIS OF MOSHER ESTER DERIVATIVES
    RIESER, MJ
    HUI, YH
    RUPPRECHT, JK
    KOZLOWSKI, JF
    WOOD, KV
    MCLAUGHLIN, JL
    HANSON, PR
    ZHUANG, ZP
    HOYE, TR
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) : 10203 - 10213
  • [8] ANNONACEOUS ACETOGENINS - A REVIEW
    RUPPRECHT, JK
    HUI, YH
    MCLAUGHLIN, JL
    [J]. JOURNAL OF NATURAL PRODUCTS, 1990, 53 (02): : 237 - 278
  • [9] Zhuang Z. B., UNPUB
  • [10] 1992, THESIS U MINNESOTA G