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
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
  • [1] Design and synthesis of orally active dispiro 1,2,4,5-tetraoxanes; synthetic antimalarials with superior activity to artemisinin
    Amewu, Richard
    Stachulski, Andrew V.
    Ward, Stephen A.
    Berry, Neil G.
    Bray, Patrick G.
    Davies, Jill
    Labat, Gael
    Vivas, Livia
    O'Neill, Paul M.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (24) : 4431 - 4436
  • [2] Amewu R, 2007, ORG BIOMOL CHEM, V5, P708
  • [3] [Anonymous], 1992, COMPREHENSIVE GUIDE
  • [4] [Anonymous], ACCIDENTAL EXPLOSION
  • [5] PREPARATION, PROPERTIES, AND REACTIONS OF CARBONYL OXIDES
    BUNNELLE, WH
    [J]. CHEMICAL REVIEWS, 1991, 91 (03) : 335 - 362
  • [6] MOLECULAR MECHANICS OF PEROXIDES .2. CYCLIC-COMPOUNDS
    CARBALLEIRA, L
    MOSQUERA, RA
    RIOS, MA
    [J]. JOURNAL OF COMPUTATIONAL CHEMISTRY, 1989, 10 (07) : 911 - 920
  • [7] Dussault P. H., 2000, PERKINS, V1, P3006
  • [8] Diastereoselectivity of additions to chiral carbonyl oxides
    Dussault, PH
    Zope, UR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (25) : 8218 - 8222
  • [9] Peroxycarbenium-mediated C-C bond formation: Applications to the synthesis of hydroperoxides and peroxides
    Dussault, PH
    Lee, IQ
    Lee, HJ
    Lee, RJ
    Niu, QJ
    Schultz, JA
    Zope, UR
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (25) : 8407 - 8414
  • [10] Endoperoxide derivatives from marine organisms: 1,2-dioxanes of the plakortin family as novel antimalarial agents
    Fattorusso, Caterina
    Campiani, Giuseppe
    Catalanotti, Bruno
    Persico, Marco
    Basilico, Nicoletta
    Parapini, Silvia
    Taramelli, Donatella
    Campagnuolo, Claudio
    Fattorusso, Ernesto
    Romano, Adriana
    Taglialatela-Scafati, Orazio
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (24) : 7088 - 7094