Synthesis of triterpenoid-based 1,2,4-trioxolanes and 1,2,4-dioxazolidines by ozonolysis of allobetulin derivatives

被引：38
|
作者：
Kazakova, Oxana B. [1 ]
Kazakov, Dmitri V. [1 ]
Yamansarov, Emil Yu. [1 ]
Medvedeva, Natal'ya I. [1 ]
Tolstikov, Genrikh A. [1 ]
Suponitsky, Kyrill Yu. [2 ]
Arkhipov, Dmitri E. [2 ]
机构：
[1] Russian Acad Sci, Ufa Res Ctr, Inst Organ Chem, Ufa 450054, Russia
[2] Russian Acad Sci, AN Nesmeyanov Organoelement Cpds Inst, Moscow 119991, Russia
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 09期
基金：
俄罗斯基础研究基金会;
关键词：
Natural products; Triterpenoids; Betulin; Antimalarials; Peroxides; 1,2,4-Trioxolanes; 1,2,4-Dioxazolidines; Ozonolysis; ANTIMALARIAL ACTIVITY; QINGHAOSU ARTEMISININ; HEME ALKYLATION; BETULINIC ACID; PEROXIDES; DRUG; TRIOXANES;
D O I：
10.1016/j.tetlet.2010.12.047
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Oxidation of allobetulin derivatives with ozone results in good isolated yields of 1,2,4-trioxolanes and stable 1,2,4-dioxazolidines. Individual 3R,5R and 3S,5S diastereoisomers of allobetulin secondary ozonides were isolated and their structures confirmed by X-ray crystallographic analysis. Remarkable diastereoselectivity with formation of only the (3S,5S)-configured peroxides was observed during the oxidation of 1,5-di-O-methoxyoximinoallobetulin to dioxazolidines. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：976 / 979
页数：4
相关论文
共 50 条
  • [41] Effect of functional group polarity on the antimalarial activity of spiro and dispiro-1,2,4-trioxolanes
    Dong, Yuxiang
    Tang, Yuanqing
    Chollet, Jacques
    Matile, Hugues
    Wittlin, Sergio
    Charman, Susan A.
    Charman, William N.
    Tomas, Josefina Santo
    Scheurer, Christian
    Snyder, Christopher
    Scorneaux, Bernard
    Bajpai, Saroi
    Alexander, Scott A.
    Wang, Xiaofang
    Padmanilayam, Manlyan
    Cheruku, Srinivasa R.
    Brun, Reto
    Vennerstrom, Jonathan L.
    BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (18) : 6368 - 6382
  • [42] Strategies for the optimization of antimalarial 1,2,4-trioxolanes: From hydrophobic prototype OZ03 to drug candidate OZ277
    Dong, YX
    Vennerstrom, JL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U2617 - U2618
  • [43] Stereoisomerism and Anticancer Activity of Tetracyclic Dispiro Ozonides (1,2,4-Trioxolanes) Obtained by the Reaction of Alicyclic 1,5-Diketones with Hydrogen Peroxide
    T. I. Akimova
    O. A. Soldatkina
    V. G. Savchenko
    N. Nekbin
    A. V. Pilipenko
    I. V. Svistunova
    S. A. Dyshlovoy
    Russian Journal of Organic Chemistry, 2025, 61 (1) : 26 - 34
  • [44] SYNTHESIS OF 1,2,4-TRIAZOLES AND 1,2,4-OXADIAZOLES
    LIN, Y
    HLAVKA, JJ
    BITHA, P
    LANG, SA
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1983, 20 (06) : 1693 - 1695
  • [45] OZONOLYSIS OF 1,2,4-TRI-TERT-BUTYLNAPHTHALENE
    ITO, Y
    MATSUURA, A
    MATSUURA, T
    JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (22): : 4300 - 4302
  • [46] SYNTHESIS OF ORGANOSILICON DERIVATIVES OF 1,2,4-TRIAZOLES
    GOLDIN, GS
    MAKSAKOV.MV
    PODDUBNY.VG
    KOLTSOVA, AN
    KISIN, AV
    TOROCHES.VN
    SIMONOVA, AA
    ZHURNAL OBSHCHEI KHIMII, 1974, 44 (01): : 115 - 119
  • [47] New Synthesis of 1,2,4-Trithiolane Derivatives
    Dorofeev, I. A.
    Shagun, L. G.
    Tokareva, I. A.
    Voronkov, M. G.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 44 (09) : 1403 - 1405
  • [48] Synthesis and structures of 1,2,4-triazoles derivatives
    Wang, Ning
    Sheng, Jun-feng
    Song, Fei
    Tong, Yu-zhu
    Wang, Zuo-xiang
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2015, 85 (03) : 746 - 751
  • [49] New synthesis of 1,2,4-trithiolane derivatives
    I. A. Dorofeev
    L. G. Shagun
    I. A. Tokareva
    M. G. Voronkov
    Russian Journal of Organic Chemistry, 2008, 44 : 1403 - 1405
  • [50] Synthesis of Novel Derivatives of 1,2,4-Triazoles
    Galstyan, Armen S.
    Ghochikyan, Tariel, V
    Frangyan, Vardges R.
    Tamazyan, Rafael A.
    Ayvazyan, Armen G.
    CHEMISTRYSELECT, 2018, 3 (35): : 9981 - 9985
12345