Stereospecific Oxidation of Diacetoxyheterobetulin with Ozone and Dimethyldioxirane

被引：0
|
作者：
Khusnutdinova, El'mira F. [1 ]
Medvedeva, Natalya I. [1 ]
Kazakov, Dmitri V. [1 ]
Kukovinets, Olga S. [1 ]
Lobov, Alexander N. [1 ]
Suponitsky, Kirill Yu. [2 ]
Kazakova, Oxana B. [1 ]
机构：
[1] Russian Acad Sci, Ufa Inst Chem, 71 Prospect Oktyabrya, Ufa 450054, Russia
[2] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, 28 Vavilova St,V-334,GSP-1, Moscow 119991, Russia
来源：
NATURAL PRODUCT COMMUNICATIONS | 2016年 / 11卷 / 04期
基金：
俄罗斯基础研究基金会;
关键词：
Triterpenoids; Oleanane; Ursane; Taraxastane; Allobetulin; Synthesis; Oxidation; Ozone; Dimethyldioxirane; Selectivity; TRITERPENOIDS; DERIVATIVES; OZONOLYSIS; EFFICIENT;
D O I：
暂无
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Stereospecific oxidation of diacetoxyheterobetulin with ozone and dimethyldioxirane led to 3 beta,28-diacetoxy-18 alpha,19 beta H-urs-20 alpha,21 alpha-epoxide with yields of 79% and 87%, respectively. Oxidation with ozone was not selective and gave two minor products containing 21 alpha-hydroxy-20(30)-ene and 21 alpha-hydroxy-20 beta,28-epoxy- fragments in ring E. The structures of 3 beta,28-diacetoxy-18 alpha,19 beta H-urs-20 alpha,21 alpha-epoxide and 3 beta-diacetoxy-21 alpha-hydroxy-20 beta,28-epoxy-18 alpha,19 beta H-ursane were confirmed by X-ray analysis for the first time.
引用
收藏
页码：449 / 452
页数：4
相关论文
共 50 条
  • [1] Oxidation of acetals by dimethyldioxirane
    Baumstark, AL
    Kovac, F
    Vasquez, PC
    HETEROCYCLIC COMMUNICATIONS, 2002, 8 (01) : 9 - 12
  • [2] Oxidation of ethers with dimethyldioxirane
    S. A. Grabovskiy
    Q. K. Timerghazin
    N. N. Kabal’nova
    Russian Chemical Bulletin, 2005, 54 : 2384 - 2393
  • [3] Oxidation of alcohols by dimethyldioxirane
    Grabovskii, SA
    Suvorkina, ES
    Kabal'nova, NN
    Khursan, SL
    Shereshovets, VV
    RUSSIAN CHEMICAL BULLETIN, 2000, 49 (08) : 1332 - 1337
  • [4] OXIDATION OF FURANS WITH DIMETHYLDIOXIRANE
    ADGER, BM
    BARRETT, C
    BRENNAN, J
    MCKERVEY, MA
    MURRAY, RW
    JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (21) : 1553 - 1554
  • [5] Oxidation of ethers with dimethyldioxirane
    Grabovskiy, SA
    Timerghazin, QK
    Kabal'nova, NN
    RUSSIAN CHEMICAL BULLETIN, 2005, 54 (10) : 2384 - 2393
  • [6] Oxidation of alcohols by dimethyldioxirane
    S. A. Grabovskii
    E. S. Suvorkina
    N. N. Kabal'nova
    S. L. Khursan
    V. V. Shereshovets
    Russian Chemical Bulletin, 2000, 49 : 1332 - 1337
  • [7] DIMETHYLDIOXIRANE - MECHANISM OF BENZALDEHYDE OXIDATION
    BAUMSTARK, AL
    BEESON, M
    VASQUEZ, PC
    TETRAHEDRON LETTERS, 1989, 30 (41) : 5567 - 5570
  • [8] DIMETHYLDIOXIRANE OXIDATION OF PRIMARY AMINES
    CRANDALL, JK
    REIX, T
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (25): : 6759 - 6764
  • [9] Selective oxidation of nitrocompounds by dimethyldioxirane
    Ballini, R
    Papa, F
    Bovicelli, P
    TETRAHEDRON LETTERS, 1996, 37 (20) : 3507 - 3510
  • [10] Oxidation of cyclic acetals with dimethyldioxirane
    Ufa State Petroleum Technical University, ul. Kosmonavtov 1, Ufa, Bashkortostan, 450062, Russia
    Dokl. Phys. Chem., 1-3 (230-231):
12345