Chemoselective oxidation of oleanolic acid derivatives with ozone

被引：0
|
作者：
O. B. Kazakova
N. I. Medvedeva
O. S. Kukovinets
G. A. Tolstikov
E. F. Khusnutdinova
L. Zaprutko
B. Bednarczyk-Cwynar
Z. Paryzek
机构：
[1] Russian Academy of Sciences,Institute of Organic Chemistry, Ufa Scientific Center
[2] Poznan University of Medical Sciences,Chair and Department of Organic Chemistry, Faculty of Pharmacy
[3] Adam Mickiewicz University,Department of Bioorganic Chemistry, Faculty of Chemistry
来源：
Chemistry of Natural Compounds | 2010年 / 46卷
关键词：
oleanolic acid; chemoselectivity; oxidation; ozonolysis;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
A method for preparing methyl esters of 12-oxoolean-28-oic and 3,12-dioxoolean-28-oic acids via ozonolysis of oleanolic acid methyl ester in CH2Cl2 at –60°C was proposed. It was found that oxidation of 2-cyano3,4-seco-4(23)-oleanenoic acid was chemoselective depending on the amount of ozone used.
引用
收藏
页码：397 / 399
页数：2
相关论文
共 50 条
  • [1] CHEMOSELECTIVE OXIDATION OF OLEANOLIC ACID DERIVATIVES WITH OZONE
    Kazakova, O. B.
    Medvedeva, N. I.
    Kukovinets, O. S.
    Tolstikov, G. A.
    Khusnutdinova, E. F.
    Zaprutko, L.
    Bednarczyk-Cwynar, B.
    Paryzek, Z.
    [J]. CHEMISTRY OF NATURAL COMPOUNDS, 2010, 46 (03) : 397 - 399
  • [2] The oxidation of oleanolic acid and acetyl oleanolic acid
    Aumuller, W
    Schicke, W
    Wedekind, E
    [J]. JUSTUS LIEBIGS ANNALEN DER CHEMIE, 1935, 517 : 211 - 228
  • [3] Catalytic Aerobic Chemoselective α-Oxidation of Acylpyrazoles en Route to α-Hydroxy Acid Derivatives
    Taninokuchi, Seiya
    Yazaki, Ryo
    Ohshima, Takashi
    [J]. ORGANIC LETTERS, 2017, 19 (12) : 3187 - 3190
  • [4] PREPARATION OF SOME DERIVATIVES OF GLYCYRRHETIC ACID AND OLEANOLIC ACID
    DEAN, PDG
    HALSALL, TG
    WHITEHOUSE, MW
    [J]. JOURNAL OF PHARMACY AND PHARMACOLOGY, 1967, 19 (10) : 682 - +
  • [5] Synthesis and cytotoxicity evaluation of oleanolic acid derivatives
    Hao, Jia
    Liu, Jun
    Wen, Xiaoan
    Sun, Hongbin
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (07) : 2074 - 2077
  • [6] Antiprotozoal Activity of Triazole Derivatives of Dehydroabietic Acid and Oleanolic Acid
    Walter Pertino, Mariano
    Vega, Celeste
    Rolon, Miriam
    Coronel, Cathia
    Rojas de Arias, Antonieta
    Schmeda-Hirschmann, Guillermo
    [J]. MOLECULES, 2017, 22 (03)
  • [7] Chemoselective aerobic oxidation of penicillin and cephalosporin derivatives into sulfoxides
    Tanaka, H
    Kikuchi, R
    Torii, S
    [J]. TETRAHEDRON, 1996, 52 (07) : 2343 - 2348
  • [8] Synthesis and α-glucosidase inhibitory activity of oleanolic acid derivatives
    Qian, Shan
    Li, Jiao Hai
    Zhang, Yu Wei
    Chen, Xin
    Wu, Yong
    [J]. JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2010, 12 (01) : 20 - 29
  • [9] Synthesis and α-Glucosidase Inhibitory Activity of Oleanolic Acid Derivatives
    Song Zhi-Cheng
    Wang Shi-Sheng
    Song Qi-Ling
    Shu Tao
    Zhao Wei-Jie
    [J]. CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2012, 33 (04): : 744 - 749
  • [10] Synthesis of oleanolic acid derivatives for inducing hair restoration
    Kang, MinSuk
    Choi, Hyunsuk
    Kim, CheongTaek
    Kwak, Young-Shin
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
12345