Synthesis of Podophyllotoxin and its Derivatives via NiCl2/NaBH4 Reduction of Isoxazoline Ring

被引:4
|
作者
Babu, Meduri Suresh [1 ]
Rai, Kuria Madhavu Lokanatha [1 ]
机构
[1] Univ Mysore, Dept Studies Chem, Mysore 570006, Karnataka, India
关键词
Nickel chloride; Isoxazoline; Podophyllotoxin; Manganese acetate; DIELS-ALDER REACTION; GAMMA-LACTONES; 1,3-DIPOLAR CYCLOADDITIONS; NITRILE OXIDES; LIGNANS; ROUTE; ANNULATION; OXIDATION; ACETATE; SERIES;
D O I
10.14233/ajchem.2013.15073
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel synthesis of podophyllotoxin was carried out in four steps. The key step was reduction of isoxazoline ring followed by diazotization and the resultant alkene was treated with Mn(OAc)(3)/CH3COOK to form podophyllotoxin.
引用
收藏
页码:9555 / 9557
页数:3
相关论文
共 50 条
  • [11] Synthesis and biological evaluation of novel 4β-(1,3,4-oxadiazole-2-amino)-podophyllotoxin derivatives
    Ren, Jie
    Wu, Lin
    Xin, Wen Qun
    Chen, Xin
    Hu, Kun
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (14) : 4778 - 4782
  • [12] Bimetallic Pd-Bi nanocatalysts derived from NaBH4 reduction of BiOCl and Pd2+ and exhibit highly efficient hydrogen production over formaldehyde solution
    Liu, Xiaogang
    Chen, Wenjie
    Zhang, Xin
    INTERNATIONAL JOURNAL OF HYDROGEN ENERGY, 2022, 47 (76) : 32425 - 32435
  • [13] Synthesis and cytotoxic activity on human cancer cells of carbamate derivatives of 4β-(1,2,3-triazol-1-yl)podophyllotoxin
    Liu, Jian-Fei
    Sang, Chun-Yan
    Xu, Xiao-Hui
    Zhang, Lin-Lin
    Yang, Xuan
    Hui, Lin
    Zhang, Jin-Bang
    Chen, Shi-Wu
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 64 : 621 - 628
  • [14] Synthesis of Ag/Bi2MoO6 Nanocomposites Using NaBH4 as Reducing Agent for Enhanced Visible-Light-Driven Photocatalysis of Rhodamine B
    Phuruangrat, Anukorn
    Keereesaensuk, Paveen-On
    Karthik, K.
    Dumrongrojthanath, Phattranit
    Ekthammathat, Nuengruethai
    Thongtem, Somchai
    Thongtem, Titipun
    JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS, 2020, 30 (02) : 322 - 329
  • [15] A convergent synthesis of alkyne-azide cycloaddition derivatives of 4-α,β-2-propyne podophyllotoxin depicting potent cytotoxic activity
    Zilla, Mahesh K.
    Nayak, Debasis
    Vishwakarma, Ram A.
    Sharma, Parduman Raj
    Goswami, Anindya
    Ali, Asif
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 77 : 47 - 55
  • [16] Synthesis of novel 2H-chromene-3-carboxylate isoxazole/isoxazoline derivatives via 1,3-dipolar cycloaddition reaction (NOAC)
    Srinivas, B.
    Krupadanam, G. L. D.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2017, 87 (02) : 331 - 339
  • [17] SnCl4 mediated synthesis of γ-amino ketones derivatives via the ring-opening reaction of 4,5-dihydropyrroles
    Zhang, Zhiguo
    Wang, Dan
    Wang, Bing
    Liu, Qingfeng
    Liu, Tongxin
    Zhang, Wei
    Yuan, Beibei
    Zhao, Zhijia
    Han, Dandan
    Zhang, Guisheng
    TETRAHEDRON, 2013, 69 (43) : 9063 - 9067
  • [18] A Convenient Synthesis of (S)-H4-BINOL and Its Derivatives via Hydrogenation of Monoesters of BINOL
    Li, Xinsheng
    Ding, Qianchang
    Ge, Jianfeng
    Xie, Jianwu
    Xu, Dongcheng
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (04): : 1785 - 1787
  • [19] Selective radical cascade (4+2) annulation with olefins towards the synthesis of chroman derivatives via organo-photoredox catalysis
    Guan, Zhipeng
    Zhong, Xingxing
    Ye, Yayu
    Li, Xiangwei
    Cong, Hengjiang
    Yi, Hong
    Zhang, Heng
    Huang, Zhiliang
    Lei, Aiwen
    CHEMICAL SCIENCE, 2022, 13 (21) : 6316 - 6321
  • [20] FIRST SYNTHESIS OF 2-TROPOLONYLQUINOLINE-4-CARBOXYLIC ACID DERIVATIVES VIA PFITZINGER REACTION IN WATER
    Gao, Wentao
    Zhang, Xiaofei
    Li, Yang
    Liu, Huaye
    Imafuku, Kimiaki
    HETEROCYCLES, 2010, 81 (07) : 1689 - 1696