Synthesis of spiro-bisperoxyketals

被引：77
作者：
Ghorai, Prasanta [1 ]
Dussault, Patrick H. [1 ]
Hu, Chunhua [2 ]
机构：
[1] Univ Nebraska, Dept Chem, Lincoln, NE 68588 USA
[2] Univ Nebraska, Nebraska Ctr Mat & Nanosci, Lincoln, NE 68588 USA
来源：
ORGANIC LETTERS | 2008年 / 10卷 / 12期
关键词：
D O I：
10.1021/ol800657m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Syntheses of spirocyclic bis-1,2-dioxolanes, bis-1,2-dioxanes, and bis-1,2-dioxepanes are achieved through intramolecular ketalizations of hydroperoxy ketones or intramolecular alkylations of gern-dihydroperoxides. The spiroperoxides have excellent thermal and chemical stability, and several display promising activity against A falciparum.
引用
收藏
页码：2401 / 2404
页数：4
相关论文
共 28 条
  • [11] Spiroacetals in insects
    Francke, W
    Kitching, W
    [J]. CURRENT ORGANIC CHEMISTRY, 2001, 5 (02) : 233 - 251
  • [12] Synthesis and antimalarial activity of novel medium-sized 1,2,4,5-tetraoxacycloalkanes
    Kim, HS
    Nagai, Y
    Ono, K
    Begum, K
    Wataya, Y
    Hamada, Y
    Tsuchiya, K
    Masuyama, A
    Nojima, M
    McCullough, KJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2001, 44 (14) : 2357 - 2361
  • [13] Korshin E. E., 2006, CHEM PEROXIDES, V2, P189, DOI DOI 10.1002/0470862769.CH5
  • [14] Co(thd)2:: a superior catalyst for aerobic epoxidation and hydroperoxysilylation of unactivated alkenes:: application to the synthesis of spiro-1,2,4-trioxanes
    O'Neill, PM
    Hindley, S
    Pugh, MD
    Davies, J
    Bray, PG
    Park, BK
    Kapu, DS
    Ward, SA
    Stocks, PA
    [J]. TETRAHEDRON LETTERS, 2003, 44 (44) : 8135 - 8138
  • [15] CHEMISTRY OF SPIROKETALS
    PERRON, F
    ALBIZATI, KF
    [J]. CHEMICAL REVIEWS, 1989, 89 (07) : 1617 - 1661
  • [16] OZONOLYSIS - INTRAMOLECULAR TRAPPING OF THE CRIEGEE INTERMEDIATE - X-RAY-ANALYSIS AND ANOMERIC EFFECT IN A 6-HYDROXY-3-METHOXY-1,2-DIOXANE
    PIERROT, M
    ELIDRISSI, M
    SANTELLI, M
    [J]. TETRAHEDRON LETTERS, 1989, 30 (04) : 461 - 462
  • [17] Structure, conformation and NMR studies on 1,2-dioxane and halogen substituted 1,2-dioxane molecules
    Senthilkumar, K
    Kolandaivel, P
    [J]. COMPUTATIONAL BIOLOGY AND CHEMISTRY, 2003, 27 (03) : 173 - 183
  • [18] Shanley E.S., 1972, ORGANIC PEROXIDES, V3, P341
  • [19] DIMETHYLALUMINUM CHLORIDE CATALYZED ENE REACTIONS OF ALDEHYDES
    SNIDER, BB
    RODINI, DJ
    KIRK, TC
    CORDOVA, R
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (02) : 555 - 563
  • [20] *SOC PLAST IND INC, 1999, SAF HANDL ORG PER AS
123