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
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
  • [41] SYNTHESIS AND CONVERSIONS OF BETA,GAMMA-UNSATURATED AMINES .19. REACTION OF 1,2,3,4-TETRACHLOROBUTANES WITH SECONDARY-AMINES
    GEGELYAN, ZG
    MIRAKYAN, SM
    MARTIROS.GT
    ARMYANSKII KHIMICHESKII ZHURNAL, 1974, 27 (04): : 314 - 318
  • [42] Synthesis of 6H-Isoindolo[2,1-a]indol-6-ones Through Wittig Reaction and Tandem Reductive Cyclization-Lactamization
    Kadam, Hari K.
    Tilve, Santosh G.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (20) : 4280 - 4284
  • [43] SYNTHESIS OF SUBSTANCES RELATED TO GIBBERELLINS .19. FURTHER EXPERIMENTS ON TOTAL SYNTHESIS OF (+-)-GIBBERELLINS A2 A4 A9 AND A10 BIOCHEMICAL STUDIES ON BAKANAE FUNGUS .77.
    MORI, K
    SHIOZAKI, M
    MATSUI, M
    SUMIKI, Y
    PROCEEDINGS OF THE JAPAN ACADEMY, 1968, 44 (07): : 717 - &
  • [44] SYNTHESIS OF NUCLEOSIDES AND RELATED-COMPOUNDS .19. 3-ACETOXY-2-DIMETHYLPHOSPHONOACRYLATES - NEW DIENOPHILES AND THEIR USE FOR THE SYNTHESIS OF CARBOCYCLIC C-NUCLEOSIDE PRECURSORS BY THE AID OF RRA REACTION
    KATAGIRI, N
    YAMAMOTO, M
    KANEKO, C
    CHEMISTRY LETTERS, 1990, (10) : 1855 - 1858
  • [45] Interfacial Reaction-Directed Green Synthesis of CeO2-MnO2 Catalysts for Imine Production through Oxidative Coupling of Alcohols and Amines
    Li, Jingwen
    Hu, Riming
    Liu, Wei
    Gao, Daowei
    Zhao, Huaiqing
    Li, Chunsheng
    Jiang, Xuchuan
    Chen, Guozhu
    INORGANIC CHEMISTRY, 2023, 62 (08) : 3692 - 3702
  • [46] Diastereoselective synthesis of 2,5-disubstituted-3-hydroxy-tetrahydrofurans through a counterion-directed Tsuji-Trost reaction
    Caumes, Xavier
    Jeanne-Julien, Louis
    Khelifi, Chakib
    Gandon, Vincent
    Roulland, Emmanuel
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (11): : 1462 - 1466
  • [47] PREPARATION OF 6,10-DIMETHYLSPIRO[4,5]DEC-6-EN-2-ONE - EXPERIMENTS DIRECTED TOWARDS SYNTHESIS OF SPIROVETIVANE SESQUITERPENES
    OGISO, A
    KURABAYA.M
    NAGAHORI, H
    MISHIMA, H
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1970, 18 (06) : 1283 - +
  • [48] STUDIES IN VILSMEIER-HAACK REACTION .19. SYNTHESIS OF ISOXAZOLO[3,2-B]QUINAZOLONE FROM 2-HYDROXY-3-METHYL-4-QUINAZOLONE
    BARNELA, SB
    SESHADRI, S
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1986, 25 (07): : 709 - 711
  • [49] Towards the Total Synthesis of Pl-3: Preparation of the Eastern Fragment through a Diastereoselective SmI2-Mediated Reformatsky Reaction
    Fuerst, Rita
    Lentsch, Christoph
    Rinner, Uwe
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (12) : 2293 - 2297
  • [50] EXPERIMENTS DIRECTED TOWARD TOTAL SYNTHESIS OF TERPENES .19. SYNTHESIS OF 8-METHOXY-4ABETA, 10BBETA,12AALPHA-TRIMETHYL-3,4,4A,4BALPHA,5,6,10B,11,12,12A-DECAHYDROCHRYSEN-1(2H)-ONE, A KEY INTERMEDIATE IN TOTAL SYNTHESIS OF (+ OR -)-SHIONONE
    IRELAND, RE
    DAWSON, MI
    KOWALSKI, CJ
    LIPINSKI, CA
    MARSHALL, DR
    TILLEY, JW
    BORDNER, J
    TRUS, BL
    JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (08): : 973 - 990