mCPBA oxidation of acetyllycoctonine and its new products

被引:11
作者
Shen, XL [1 ]
Wang, FP [1 ]
机构
[1] Sichuan Univ, W China Coll Pharm, Dept Chem Med Nat Prod, Chengdu 610041, Peoples R China
关键词
C-19-diterpenoid alkaloid; acetyllycoctonine; oxidation involving nitrogen atom; N-oxidation;
D O I
10.1248/cpb.53.267
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Treatment of a lycoctonine-type alkaloid acetyllycoctonine (4) with mCPBA at room temperature led to acetyllycoctonine N-oxide (5) as the major product together with other interesting compounds 6-12 as the minor products, which were derived from oxidation involving the nitrogen atom(1)) and Cope elimination as well as Polonovski-like fragmentation. All of those new compounds (5-12) were fully characterized.
引用
收藏
页码:267 / 270
页数:4
相关论文
共 11 条
  • [1] N-OXIDES OF SOME NORDITERPENOID ALKALOIDS
    BAI, YL
    DESAI, HK
    PELLETIER, SW
    [J]. JOURNAL OF NATURAL PRODUCTS-LLOYDIA, 1995, 58 (06): : 929 - 933
  • [2] BENN MH, 1983, ALKALOIDS CHEM BIOL, V1, P120
  • [3] A novel conversion of norditerpenoid alkaloids into aconane-type diterpenes
    Chen, QH
    Xu, L
    Wang, FP
    [J]. TETRAHEDRON, 2002, 58 (46) : 9431 - 9444
  • [4] Dzhakhangirov FN, 1997, KHIM PRIRODNYK SOEDI, P254
  • [5] PERACID OXIDATION OF IMINES - KINETICS OF OXAZIRANE FORMATION FROM BENZYLIDENE-TERT-BUTYLAMINES AND PERBENZOIC ACID
    OGATA, Y
    SAWAKI, Y
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (14) : 4687 - 4692
  • [6] Pelletier SW., 1977, HETEROCYCLES, V7, P327, DOI DOI 10.3987/S-1977-01-0327
  • [7] Wang F. P., 1989, W CHINA J PHARM SCI, V4, P193
  • [8] Wang F.-P., 1992, ALKALOIDS, V42, P151
  • [9] Wang F. P., 1991, CHINESE CHEM LETT, V2, P103
  • [10] Wang Feng-Peng, 2002, Alkaloids Chem Biol, V59, P1, DOI 10.1016/S0099-9598(02)59008-8