A SHORT, CONVERGENT SYNTHESIS OF ARISTOLINDIQUINONE

被引:21
作者
BOTHA, ME [1 ]
GILES, RGF [1 ]
YORKE, SC [1 ]
机构
[1] UNIV CAPE TOWN,DEPT CHEM,RONDEBOSCH 7700,SOUTH AFRICA
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1991年 / 01期
关键词
D O I
10.1039/p19910000085
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aristolindiquinone, 2,5-dihydroxy-3,8-dimethyl-1,4-naphthoquinone 1, is synthesised by the regiochemical addition of 1-methoxy-1-trimethylsiloxypenta-1,3-diene 2 to 5-bromo-2-methoxy-3-methyl-1,4-benzoquinone 3. The regioisomer 2,8-dihydroxy-3,5-dimethyl-1,4-naphthoquinone 4 is prepared by reaction of the same diene 2 with 2-methoxy-3-methyl-1,4-benzoquinone 11. The former reaction readily provided sufficient quantities of aristolindiquinone 1 for biological evaluation for fertility regulation in rats, for which purpose it was found to be inactive.
引用
收藏
页码:85 / 88
页数:4
相关论文
共 22 条
  • [1] STUDIES ON INDIAN MEDICINAL-PLANTS .79. SYNTHESIS PROVES THE STRUCTURE OF ARISTOLINDIQUINONE
    ACHARI, B
    BANDYOPADHYAY, S
    BASU, K
    PAKRASHI, SC
    [J]. TETRAHEDRON, 1985, 41 (01) : 107 - 110
  • [2] A CONVENIENT SYNTHESIS OF 7-METHOXYMITOSENE BY THE PHOTOLYSIS OF AMINOBENZOQUINONES
    AKIBA, M
    IKUTA, S
    TAKADA, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1983, (15) : 817 - 818
  • [3] REACTIONS OF KETEN ACETALS .7. TOTAL SYNTHESES OF TETRAMETHYL ETHERS OF 1-ACYL-2,4,5,7-TETRAHYDROXYANTHRAQUINONES RHODOLAMPROMETRIN AND RHODOCOMATULIN
    BANVILLE, J
    BRASSARD, P
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (17): : 1852 - 1856
  • [4] BUCHTA E, 1952, LIEBIGS ANN CHEM, V576, P155
  • [5] SYNTHESIS OF INSECT DYESTUFF KERMESIC ACID AND RELATED ANTHRAQUINONES
    CAMERON, DW
    FEUTRILL, GI
    GRIFFITHS, PG
    HODDER, DJ
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1978, (16) : 688 - 689
  • [6] CHEMISTRY OF THE COCCOIDEA .7. SYNTHESIS OF CEROALBOLINIC ACID
    CAMERON, DW
    CONN, C
    FEUTRILL, GI
    [J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1981, 34 (09) : 1945 - 1949
  • [7] STUDIES ON ARISTOLOCHIA .3. ISOLATION AND BIOLOGICAL EVALUATION OF CONSTITUENTS OF ARISTOLOCHIA-INDICA ROOTS FOR FERTILITY-REGULATING ACTIVITY
    CHE, CT
    AHMED, MS
    KANG, SS
    WALLER, DP
    BINGEL, AS
    MARTIN, A
    RAJAMAHENDRAN, P
    BUNYAPRAPHATSARA, N
    LANKIN, DC
    CORDELL, GA
    SOEJARTO, DD
    WIJESEKERA, ROB
    FONG, HHS
    [J]. JOURNAL OF NATURAL PRODUCTS, 1984, 47 (02): : 331 - 341
  • [8] STUDIES ON ARISTOLOCHIA .2. ARISTOLINDIQUINONE - A NEW NAPHTHOQUINONE FROM ARISTOLOCHIA-INDICA L (ARISTOLOCHIACEAE)
    CHE, CT
    CORDELL, GA
    FONG, HHS
    EVANS, CA
    [J]. TETRAHEDRON LETTERS, 1983, 24 (13) : 1333 - 1336
  • [9] STRUCTURE OF 2,5-DIHYDROXY-3,8-DIMETHYL-1,4-NAPHTHALENEDIONE (ARISTOLINDIQUINONE)
    COWE, HJ
    COX, PJ
    CORDELL, GA
    CHE, CT
    FONG, HHS
    HOWIE, RA
    [J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1986, 42 : 1533 - 1535
  • [10] DIELS-ALDER REACTIONS OF 1,1-DIMETHOXY-3-TRIMETHYLSILYLOXY-1,3-BUTADIENE
    DANISHEFSKY, S
    SINGH, RK
    GAMMILL, RB
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (02) : 379 - 380