EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .19. ELABORATION OF 2-FORMYLQUINIZARIN THROUGH A WITTIG REACTION

被引：2
|
作者：
BONIFACE, PJ [1 ]
CAMBIE, RC [1 ]
CARROLL, DR [1 ]
MARSH, NF [1 ]
MILBANK, JBJ [1 ]
RUTLEDGE, PS [1 ]
WOODGATE, PD [1 ]
机构：
[1] UNIV AUCKLAND,DEPT CHEM,PRIVATE BAG 92019,AUCKLAND,NEW ZEALAND
来源：
AUSTRALIAN JOURNAL OF CHEMISTRY | 1994年 / 47卷 / 03期
关键词：
D O I：
10.1071/CH9940441
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Reaction of 2-formylquinizarin dimethyl ether (3) with the dimethoxy ylide (6) gives an alpha,beta-unsaturated ester (8) which on hydrogenation, reduction and methylation gives the tetramethoxyanthracene diester (18). When linked to work by Dotz and Popall this sequence provides a route to (+/-)-4-demethoxydaunomycinone.
引用
收藏
页码：441 / 449
页数：9
相关论文
共 50 条
  • [1] Experiments directed towards the synthesis of anthracyclinones. XIX. Elaboration of 2-formylquinizarin through a Wittig reaction
    Boniface, Peter J.
    Cambie, Richard C.
    Carroll, David R.
    Marsh, Nicholas F.
    Milbank, Jared B.J.
    Rutledge, Peter S.
    Woodgate, Paul D.
    Australian Journal of Chemistry, 1994, 47 (03)
  • [2] EXPERIMENTS DIRECTED TOWARDS SYNTHESIS OF ANTHRACYCLINONES .1. SYNTHESIS OF 2-FORMYLMETHOXYANTHRAQUINONES
    ROBERTS, JL
    RUTLEDGE, PS
    TREBILCOCK, MJ
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1977, 30 (07) : 1553 - 1560
  • [3] Experiments directed towards the synthesis of anthracyclinones. XXXVI - Asymmetric dihydroxylations of alkylidene anthracyclinones
    Cambie, RC
    Clark, RB
    Rustenhoven, JJ
    Rutledge, PS
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1999, 52 (08) : 781 - 800
  • [4] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .14. AN INTERMEDIATE FOR THE SYNTHESIS OF VINEOMYCINS
    CAMBIE, RC
    HOWE, TA
    PAUSLER, MG
    RUTLEDGE, PS
    WOODGATE, PD
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1987, 40 (06) : 1063 - 1072
  • [5] Experiments directed towards the synthesis of anthracyclinones. XXXII - Synthesis of anthraquinone aldehydes
    Bercich, MD
    Cambie, RC
    Rutledge, PS
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1999, 52 (04) : 241 - 257
  • [6] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .13. OZONOLYSES OF ANTHRAFURANS
    CAMBIE, RC
    LARSEN, DS
    RUTLEDGE, PS
    WOODGATE, PD
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1987, 40 (01) : 215 - 222
  • [7] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .10. A SYNTHESIS OF (+/-)-4-DEMETHOXYDAUNOMYCINONE
    CAMBIE, RC
    LARSEN, DS
    RICKARD, CEF
    RUTLEDGE, PS
    WOODGATE, PD
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1986, 39 (03) : 487 - 502
  • [8] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .23. A SYNTHESIS OF FRIDAMYCIN-E
    PAUSLER, MG
    RUTLEDGE, PS
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (12) : 2135 - 2147
  • [9] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .22. NOVEL CYCLOPROPANATION REACTIONS
    CAMBIE, RC
    DUDDING, SM
    HIGGS, KC
    HOLROYD, SE
    RUTLEDGE, PS
    WOODGATE, PD
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1994, 47 (08) : 1561 - 1577
  • [10] EXPERIMENTS DIRECTED TOWARDS THE SYNTHESIS OF ANTHRACYCLINONES .26. THE PREPARATION OF CHIRAL INTERMEDIATES FOR ANTHRACYCLINONE SYNTHESIS
    BEAUREGARD, DA
    CAMBIE, RC
    DANSTED, PC
    RUTLEDGE, PS
    WOODGATE, PD
    AUSTRALIAN JOURNAL OF CHEMISTRY, 1995, 48 (03) : 669 - 676
12345