TOTAL SYNTHESIS OF ISOROBUSTIN

被引:24
作者
BARTON, DHR
DONNELLY, DMX
FINET, JP
GUIRY, PJ
机构
[1] NATL UNIV IRELAND UNIV COLL DUBLIN,DEPT CHEM,DUBLIN 4,IRELAND
[2] TEXAS A&M UNIV SYST,DEPT CHEM,COLLEGE STN,TX 77843
[3] UNIV PROVENCE,SREP LAB,CNRS,URA 1412,F-13397 MARSEILLE 13,FRANCE
关键词
D O I
10.1016/S0040-4039(00)88512-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of isorobustin 1 in four steps from 5-methoxyresorcinol proceeds in an overall yield of 34%. The key step involves the arylation of a 4-hydroxy-2H-1-benzopyran-2-one 6 by 3,4-methylenedioxyphenyllead triacetate 9 in a chemoselective and regioselective manner.
引用
收藏
页码:7449 / 7452
页数:4
相关论文
共 20 条
  • [1] SYNTHESIS OF LINEAR 3-PHENYLPYRANOCOUMARINS - SYNTHESIS OF ROBUSTIN, ROBUSTIC ACID, AND THEIR METHYL ETHERS
    AHLUWALIA, VK
    PRAKASH, C
    JOLLY, RS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (06): : 1697 - 1702
  • [2] ALLEN RD, 1969, TETRAHEDRON LETT, P4673
  • [3] STERIC AND ELECTRONIC FACTORS WHICH EFFECT THERMAL CYCLIZATION OF META-SUBSTITUTED ARYL PROPARGYL ETHERS - SYNTHESIS OF 5-SUBSTITUTED AND 7-SUBSTITUTED 3-CHROMENES
    ANDERSON, WK
    LAVOIE, EJ
    WHITKOP, PG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (07) : 881 - 884
  • [4] NOVEL METHODS FOR SYNTHESIS OF 2-2-DIMETHYLCHROMENS
    BANDARANAYAKE, WM
    CROMBIE, L
    WHITING, DA
    [J]. JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1969, (17): : 970 - +
  • [5] BANDARANAYAKE WM, 1970, J CHEM SOC C, P811
  • [6] THE FACILE SYNTHESIS OF A VERY HINDERED PHENOL BY LIGAND COUPLING
    BARTON, DHR
    DONNELLY, DMX
    GUIRY, PJ
    REIBENSPIES, JH
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (16) : 1110 - 1111
  • [7] A FACILE SYNTHESIS OF 3-ARYL-4-HYDROXYCOUMARINS
    BARTON, DHR
    DONNELLY, DMX
    FINET, JP
    GUIRY, PJ
    [J]. TETRAHEDRON LETTERS, 1989, 30 (12) : 1539 - 1542
  • [8] Dean F. M., 1963, NATURALLY OCCURRING, P16
  • [9] DEWICK PM, 1988, FLAVONOIDS ADV RES 1, P125
  • [10] PREPARATION OF SOME ARYLTRIALKYL- AND TETRAARYL-STANNANES
    EABORN, C
    HORNFELD, HL
    WALTON, DRM
    [J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1967, 10 (03) : 529 - &