Synthesis of lupane and 19β,28-epoxy-18α-oleanane 2,3-seco-derivatives based on betulin

被引:24
作者
Tolmacheva, I. A. [1 ]
Nazarov, A. V. [1 ]
Maiorova, O. A. [1 ]
Grishko, V. V. [1 ]
机构
[1] Russian Acad Sci, Ural Branch, Inst Chem Engn, Perm 614013, Russia
关键词
2,3-seco-triterpenoids; betulin; allobetulin; Beckmann fragmentation;
D O I
10.1007/s10600-008-9135-7
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
The alpha-hydroxyoximes of methyl betulonate and allobetulone were synthesized. Beckmann fragmentation of them produced the lupane and 19 beta,28-epoxy-18 alpha-oleanane 2,3-seco-derivatives.
引用
收藏
页码:606 / 611
页数:6
相关论文
共 15 条
  • [1] CSUK R, 1997, SYNTHETIC COMMUN, V27, P1607
  • [2] Fieser M, 1974, REAGENTS ORGANIC SYN
  • [3] Flekhter O. B., 2002, Khimiko-Farmatsevticheskii Zhurnal, V36, P26
  • [4] Keil B, 1961, LABORATORIUMSTECHNIK
  • [5] Birch bark research and development
    Krasutsky, Pavel A.
    [J]. NATURAL PRODUCT REPORTS, 2006, 23 (06) : 919 - 942
  • [6] Synthesis of 16,17-seco-steroids with iminomethyl-2-pyridine and aminomethylene-2-pyridine structures as chiral ligands for copper ions and molecular oxygen activation
    Magyar, A
    Schönecker, B
    Wölfling, J
    Schneider, G
    Günther, W
    Görls, H
    [J]. TETRAHEDRON-ASYMMETRY, 2003, 14 (18) : 2705 - 2715
  • [7] BECKMANN FRAGMENTATION REACTION OF 3-METHOXY-17BETA-HYDROXYESTRA-1,3,5(10)-TRIEN-16-ONE OXIME
    MILJKOVIC, D
    PETROVIC, J
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (12) : 2101 - 2102
  • [8] SYNTHESIS AND UNUSUAL BECKMANN FRAGMENTATION REACTION OF SYN-3-METHOXY-6-ALPHA,17-BETA-DIHYDROXYESTRA-1,3,5(10)-TRIEN-7-ONE OXIME
    PEJANOVIC, VM
    PETROVIC, JA
    CSANADI, JJ
    STANKOVIC, SM
    MILJKOVIC, DA
    [J]. TETRAHEDRON, 1995, 51 (48) : 13379 - 13384
  • [9] Selective oxidation of betulin for the preparation of betulinic acid, an antitumoral compound
    Pichette, A
    Liu, HY
    Roy, C
    Tanguay, S
    Simard, F
    Lavoie, S
    [J]. SYNTHETIC COMMUNICATIONS, 2004, 34 (21) : 3925 - 3937
  • [10] Schulze H., 1922, BER, P2332