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
  • [31] Oxidation of iron(III) tetramesitylporphyrin with dimethyldioxirane
    Wolowiec, S
    Latos-Grazynski, L
    INORGANIC CHEMISTRY, 1998, 37 (12) : 2984 - 2988
  • [32] Stereospecific Oxidation of Diacetoxyheterobetulin with Ozone and Dimethyldioxirane
    Khusnutdinova, El'mira F.
    Medvedeva, Natalya I.
    Kazakov, Dmitri V.
    Kukovinets, Olga S.
    Lobov, Alexander N.
    Suponitsky, Kirill Yu.
    Kazakova, Oxana B.
    NATURAL PRODUCT COMMUNICATIONS, 2016, 11 (04) : 449 - 452
  • [33] Oxidation of secondary alcohols and ethers by dimethyldioxirane
    Baumstark, AL
    Kovac, F
    Vasquez, PC
    CANADIAN JOURNAL OF CHEMISTRY, 1999, 77 (03) : 308 - 312
  • [34] AN EXTREMELY EFFICIENT SYNTHESIS OF THIOPHENE 1,1-DIOXIDES - OXIDATION OF THIOPHENE DERIVATIVES WITH DIMETHYLDIOXIRANE
    MIYAHARA, Y
    INAZU, T
    TETRAHEDRON LETTERS, 1990, 31 (41) : 5955 - 5958
  • [35] DIMETHYLDIOXIRANE OXIDATION OF 3-ARYLIDENECHROMANONES
    ADAM, W
    HALASZ, J
    LEVAI, A
    NEMES, C
    PATONAY, T
    TOTH, G
    LIEBIGS ANNALEN DER CHEMIE, 1994, (08): : 795 - 803
  • [36] Oxidation of betulin and its acetates with dimethyldioxirane
    Ashavina, OY
    Kabalnova, NN
    Flekhter, OB
    Spirikhin, LV
    Galin, FZ
    Baltina, LA
    Starikova, ZA
    Antipin, MY
    Tolstikov, GA
    MENDELEEV COMMUNICATIONS, 2004, 14 (05) : 221 - 223
  • [37] IMINES AND DERIVATIVES .24. NITRONE SYNTHESIS BY IMINE OXIDATION USING EITHER A PEROXYACID OR DIMETHYLDIOXIRANE
    BOYD, DR
    COULTER, PB
    MCGUCKIN, MR
    SHARMA, ND
    JENNINGS, WB
    WILSON, VE
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1990, (02): : 301 - 306
  • [38] TRANSFORMATIONS OF SOLASODINE AND DERIVATIVES OF HECOGENIN BY CUNNINGHAMELLA-ELEGANS
    PATEL, AV
    BLUNDEN, G
    CRABB, TA
    PHYTOCHEMISTRY, 1994, 35 (01) : 125 - 133
  • [39] EPOXIDATION VERSUS ALLYLIC OXIDATION (CH INSERTION) IN THE OXYFUNCTIONALIZATION OF VINYLSILANES AND BETA-HYDROXY DERIVATIVES BY DIMETHYLDIOXIRANE
    ADAM, W
    PRECHTL, F
    RICHTER, MJ
    SMERZ, AK
    TETRAHEDRON LETTERS, 1995, 36 (28) : 4991 - 4994
  • [40] Oxidation of 1,3-dioxacycloalkanes with dimethyldioxirane
    Akbalina, ZF
    Abushakhmina, GM
    Kabal'nova, NN
    Zlotskii, SS
    Shereshovets, VV
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2002, 72 (09) : 1406 - 1409
12345