Synthesis of a 1,2,7,8-tetraoxa-spiro[5.5]undecane

被引:19
作者
Zhang, Qi [1 ]
Li, Yun [1 ]
Wu, Yi-Kang [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Bio Organic & Nat Prod Chem, Shanghai 200032, Peoples R China
关键词
peroxide; antimalarial; artemisinin; hydrogen peroxide; spiro compound;
D O I
10.1002/cjoc.200790242
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Synthesis of a new spiro organic peroxide is described. The peroxy bonds were incorporated into the substrate framework via an acid-catalyzed ketal exchange reaction using hydrogen peroxide as the source of peroxy linkage. The hydroperoxyl groups were then bonded at the OH ends via Hg(II)-induced electrophilic additions to the C-C double bonds, giving a novel sprio structure with one peroxy bond in each of the two six-membered rings. The ester functionalities in the side chains also make it possible to conduct further structural modifications.
引用
收藏
页码:1304 / 1308
页数:5
相关论文
共 28 条
  • [1] Unprecedented, selective Nef reaction of secondary nitroalkanes promoted by DBU under basic homogeneous conditions
    Ballini, R
    Bosica, G
    Fiorini, D
    Petrini, M
    [J]. TETRAHEDRON LETTERS, 2002, 43 (30) : 5233 - 5235
  • [2] REGIOSELECTIVITY IN PHOTOCHEMICAL CHLOROCARBONYLATION OF CARBONYL-COMPOUNDS
    BASHIRHASHEMI, A
    HARDEE, JR
    GELBER, N
    QI, LD
    AXENROD, T
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (08) : 2132 - 2134
  • [3] CHASAR DW, 1982, SYNTHESIS-STUTTGART, P841
  • [4] *CHIN COOP RES GRO, 1982, J TRADIT CHIN MED, V2, P17
  • [5] NEW CYCLOTRIDECANE PEROXIDES
    DASNES, T
    LEDAAL, T
    [J]. ACTA CHEMICA SCANDINAVICA, 1971, 25 (05): : 1906 - &
  • [6] Synthesis and antimalarial activity of 11 dispiro-1,2,4,5-tetraoxane analogues of WR 148999. 7,8,15,16-tetraoxadispiro[5.2.5.2]hexadecanes substituted at the 1 and 10 positions with unsaturated and polar functional groups
    Dong, YX
    Matile, H
    Chollet, J
    Kaminsky, R
    Wood, JK
    Vennerstrom, JL
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (08) : 1477 - 1480
  • [7] Design, synthesis and in vitro antimalarial activity of spiroperoxides
    Jin, Hong-Xia
    Zhang, Qi
    Kim, Hye-Sook
    Wataya, Yusuke
    Liu, He-Hua
    Wu, Yikang
    [J]. TETRAHEDRON, 2006, 62 (33) : 7699 - 7711
  • [8] Karimi B, 1999, SYNLETT, P1456
  • [9] Synthesis and antimalarial activity of cyclic peroxides, 1,2,4,5,7-pentoxocanes and 1,2,4,5-tetroxanes
    Kim, HS
    Shibata, Y
    Wataya, Y
    Tsuchiya, K
    Masuyama, A
    Nojima, M
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (14) : 2604 - 2609
  • [10] QINGHAOSU (ARTEMISININ) - AN ANTIMALARIAL DRUG FROM CHINA
    KLAYMAN, DL
    [J]. SCIENCE, 1985, 228 (4703) : 1049 - 1055