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 [J].
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 [J].
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 [J].
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 [J].
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 [J].
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) [J].
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 [J].
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 [J].
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 [J].
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 [J].
Gao, Wentao ;
Zhang, Xiaofei ;
Li, Yang ;
Liu, Huaye ;
Imafuku, Kimiaki .
HETEROCYCLES, 2010, 81 (07) :1689-1696