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
  • [41] Synthesis of Thiazole-Fused Diosgenin Derivatives as Potential Therapeutic Agents
    Roy, Subrata
    Budhathoki, Shailesh
    Alam, Mohammad Abrar
    CHEMISTRYSELECT, 2024, 9 (40):
  • [42] Design, synthesis and cytotoxic activity of novel lipophilic cationic derivatives of diosgenin and sarsasapogenin
    An, Ren-Feng
    Wu, Kai-Tian
    Pan, Jie
    Zhang, Wen-Jin
    Qin, Hui-Ying
    Li, Xiao-Rui
    Liu, Wei
    Huang, Xue-Feng
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2025, 119
  • [43] Synthesis and Antitumor Activity of Diosgenin Hydroxamic Acid and Quaternary Phosphonium Salt Derivatives
    Wang, Lin
    Yao, Maoling
    Hu, Yuegao
    Chen, Congdi
    Jin, Liming
    Ma, Xiaodong
    Yang, Hongjun
    ACS MEDICINAL CHEMISTRY LETTERS, 2022, 13 (05): : 786 - 791
  • [44] Recent advances in chemical synthesis, biocatalysis, and biological evaluation of diosgenin derivatives - A review
    Fan, Ruolan
    He, Weishen
    Fan, Yong
    Xu, Wen
    Xu, Wei
    Yan, Guohong
    Xu, Shaohua
    STEROIDS, 2022, 180
  • [45] GENERATION OF 1,2-DIOXETANE DECOMPOSITION PRODUCTS IN THE OXIDATION OF 3-PHENYL-2-METHYLBENZOFURAN EPOXIDE BY DIMETHYLDIOXIRANE AND THE OXODIPEROXOMOLYBDENUM COMPLEX
    ADAM, W
    SAUTER, M
    TETRAHEDRON, 1994, 50 (28) : 8393 - 8398
  • [46] High-yield synthesis of nitriles by oxidation of aldehyde N,N-dimethylhydrazones with dimethyldioxirane
    Altamura, A
    D'Accolti, L
    Detomaso, A
    Dinoi, A
    Fiorentino, M
    Fusco, C
    Curci, R
    TETRAHEDRON LETTERS, 1998, 39 (14) : 2009 - 2012
  • [47] In situ epoxide generation by dimethyldioxirane oxidation and the use of epichlorohydrin in the flow synthesis of a library of β-amino alcohols
    Cossar, Peter J.
    Baker, Jennifer R.
    Cain, Nicholas
    McCluskey, Adam
    ROYAL SOCIETY OPEN SCIENCE, 2018, 5 (04):
  • [48] Oxidation of 3-arylisochromans by dimethyldioxirane. An easy route to substituted 3-arylisocoumarins.
    Bovicelli, P
    Lupattelli, P
    Crescenzi, B
    Sanetti, A
    Bernini, R
    TETRAHEDRON, 1999, 55 (51) : 14719 - 14728
  • [49] Effect of β-Cyclodextrin Derivatives on the Diosgenin Absorption in Caco-2 Cell Monolayer and Rats
    Okawara, Masaki
    Tokudome, Yoshihiro
    Todo, Hiroaki
    Sugibayashi, Kenji
    Hashimoto, Fumie
    BIOLOGICAL & PHARMACEUTICAL BULLETIN, 2014, 37 (01) : 54 - 59
  • [50] Antioxidant activity of novel diosgenin derivatives: Synthesis, biological evaluation, and in silico ADME prediction
    Michalak, Olga
    Krzeczynski, Piotr
    Jaromin, Anna
    Cmoch, Piotr
    Cybulski, Marcin
    Trzcinska, Kinga
    Miszta, Przemyslaw
    Mehta, Pakhuri
    Gubernator, Jerzy
    Filipek, Slawomir
    STEROIDS, 2022, 188
12345