Oxidation of hecogenin and diosgenin derivatives with dimethyldioxirane

被引：0
|
作者：
Zhu, BK
Zhang, HB
Zhang, YS
Zhong, HM
Liu, JP [1 ]
机构：
[1] Yunnan Univ, Ctr Adv Studies Med & Organ Chem, Sch Pharm, Kunming 650091, Peoples R China
[2] Qingdao Sci & Tech Univ, Sch Chem, Qingdao 266042, Peoples R China
来源：
CHINESE CHEMICAL LETTERS | 2005年 / 16卷 / 02期
关键词：
oxidation; dimethyldioxirane; hecogenin; diosgenin; derivative;
D O I：
暂无
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Diacetyl derivative of hecogenin 1 was oxidized to unsaturated ketone 5 via allylic alcohol 3 when it reacted with dimethyldioxirane (DMDO). The structure of 3 was confirmed by X-ray crystal analysis and the highly regioselectivity of DMDO to different olefin bonds was also observed when diosgenin derivative 6 was treated with DMDO.
引用
收藏
页码：143 / 146
页数：4
相关论文
共 50 条
  • [21] Cyclic acetals oxidation by dimethyldioxirane
    Rakhmankulov, DL
    Zlotskii, SS
    Shereshovets, VV
    Abushakhmina, GM
    Kabal'nova, NN
    DOKLADY AKADEMII NAUK, 1998, 361 (03) : 355 - 356
  • [22] Oxidation of diterpenoid alkaloids with dimethyldioxirane
    Zinurova, EG
    Kabal'nova, NN
    Shereshovets, VV
    Ivanova, EV
    Shults, EE
    Tolstikov, GA
    Yunusov, MS
    RUSSIAN CHEMICAL BULLETIN, 2001, 50 (04) : 720 - 723
  • [23] Synthesis and dimethyldioxirane oxidation of tetrahydrobenzofurans
    Lévai, A
    Kocevar, M
    Tóth, G
    Simon, A
    Vranicar, L
    Adam, W
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002, 2002 (11) : 1830 - 1833
  • [24] Oxidation of diterpenoid alkaloids with dimethyldioxirane
    E. G. Zinurova
    N. N. Kabal"nova
    V. V. Shereshovets
    E. V. Ivanova
    E. E. Shults
    G. A. Tolstikov
    M. S. Yunusov
    Russian Chemical Bulletin, 2001, 50 : 720 - 723
  • [25] A NEW AND EFFICIENT SYNTHESIS OF CYTIDINE AND ADENOSINE DERIVATIVES BY DIMETHYLDIOXIRANE OXIDATION OF THIOPYRIMIDINE AND THIOPURINE NUCLEOSIDES
    SALADINO, R
    CRESTINI, C
    BERNINI, R
    FRACHEY, G
    MINCIONE, E
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (21): : 3053 - 3054
  • [26] The dimethyldioxirane-mediated oxidation of phenylethyne
    Zeller, KP
    Kowallik, M
    Haiss, P
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (12) : 2310 - 2318
  • [27] THE FORMATION OF ORTHOQUINONES IN THE DIMETHYLDIOXIRANE OXIDATION OF PHENOLS
    CRANDALL, JK
    ZUCCO, M
    KIRSCH, RS
    COPPERT, DM
    TETRAHEDRON LETTERS, 1991, 32 (40) : 5441 - 5444
  • [28] Chemiluminescence in the oxidation of europium β-diketonates by dimethyldioxirane
    Kazakov, DV
    Maistrenko, GY
    Kotchneva, OA
    Latypova, RR
    Kazakov, VP
    MENDELEEV COMMUNICATIONS, 2001, (05) : 188 - 190
  • [29] Epoxidation versus allylic oxidation (CH insertion) in the oxyfunctionalization of vinylsilanes and QQ -hydroxy derivatives by dimethyldioxirane
    Tetrahedron Lett, 28 (4991):
  • [30] Dimethyldioxirane oxidation of (E,E)-cinnamylideneacetophenones
    Lévai, A
    Silva, AMS
    Cavaleiro, JAS
    Patonay, T
    Silva, VLM
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2001, 2001 (17) : 3213 - 3219
12345