Citation: Xu Zhaohui, Li Yuyu, Liu Deyong, Xiao Qiang. Highly Efficent Synthesis of Novel Gastrodine Intermediate Analogues[J]. Chinese Journal of Organic Chemistry, ;2018, 38(11): 3118-3122. doi: 10.6023/cjoc201804005 shu

Highly Efficent Synthesis of Novel Gastrodine Intermediate Analogues

Xu Zhaohui ^a,, ,
Li Yuyu ^a ,
Liu Deyong ^a ,
Xiao Qiang ^b,,

a.
Department of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang 330027
b.
Department of Orthpaedics, Jiangxi Province People's Hospital, Nanchang 330006

Corresponding author: Xu Zhaohui, gotoxzh@163.com Xiao Qiang,
Received Date: 2 April 2018
Revised Date: 15 May 2018
Available Online: 5 November 2018
Fund Project: the Science and Technology Research Project of Jiangxi Provincial Education Department GJJ170170the National Natural Science Foundation of China 81760297the Graduate Innovation Fundation of Jiangxi Province YC2015-B023Project supported by the National Natural Science Foundation of China (No. 81760297), the Graduate Innovation Fundation of Jiangxi Province (No. YC2015-B023) and the Science and Technology Research Project of Jiangxi Provincial Education Department (No. GJJ170170)

Figures(2)

Ten gastrodine intermediate analogues were synthesized by the Knoevenagel reaction of 4-formylphenyl(2, 3, 4, 6-tetra-O-acetyl)-β-D-glucoside and 1, 3-dioxane-4, 6-dione with gluconic acid as a catalyst. In this reaction there are many advantages with good to excellent yields (78%~92%), mild conditions, simple operations and environmental friendliness. Additionally, gluconic acid could be recycled and reused many times without lossing its efficiency.
- gluconic acid,
- Knoevenagel reaction,
- 4-formylphenyl (2, 3, 4, 6-tetra-O-acetyl)-β-D-glucoside,
- gastrodine intermediate analogues
1. [1]
  Wang, M. W.; Hao, X.; Chen, K. Philos. Trans. R. Soc., B 2007, 362, 1093. doi: 10.1098/rstb.2007.2036
2. [2]
  Zhou, J. Acta Chim. Sin. 1980, 38, 7.
3. [3]
  Liu, J.; Mori, A. Neuropharmacology 1992, 31, 1287. doi: 10.1016/0028-3908(92)90058-W
4. [4]
  Park, S.; Kim, D. S.; Kang, S. Appl. Environ. Microbiol. 1994, 60, 3903.
5. [5]
  Ahn, E. K.; Jeon, H. J.; Lim, E. J.; Jung, H. J. J. Ethnopharmacol. 2007, 110, 476. doi: 10.1016/j.jep.2006.10.006
6. [6]
  Sha, J. Z.; Mao, H. K. Chin. Pharm. Bull. 1987, 22, 27(in Chinese).
7. [7]
  Wu, C. R.; Hsieh, M. T.; Huang, S. C.; Chang, W. H.; Chen, C. F. Planta Med. 1996, 62, 317. doi: 10.1055/s-2006-957892
8. [8]
  Wen, H.; Lin, C. L.; Ling, Q.; Ge, H.; Ma, L.; Cao, R. H.; Wan, Y. Q.; Peng, W. L.; Wang, Z. H.; Song, H. C. Eur. J. Med. Chem. 2008, 43, 166. doi: 10.1016/j.ejmech.2007.03.018
9. [9]
  Zhu, Q. L.; Tang, Q.; Li, Y.; Yin, S. F. Chin. J. Org. Chem. 2006, 26, 1264(in Chinese). doi: 10.3321/j.issn:0253-2786.2006.09.014
10. [10]
  Hu, C.; Yang, H. J.; Yin, S. F. Chin. J. Org. Chem. 2009, 29, 89(in Chinese).
11. [11]
  Zheng, L.; Yin, X. J.; Yang, C. L.; Li, Y.; Yin, S. F. Chem. J. Nat. Compd. 2011, 47, 170. doi: 10.1007/s10600-011-9873-9
12. [12]
  Chen, B. C. Heterocyles 1991, 32, 529. doi: 10.3987/REV-90-422
13. [13]
14. [14]
  Fillion, E.; Dumas, A. M.; Hogg, S. A. J. Org. Chem. 2006, 71, 9899. doi: 10.1021/jo0618876
15. [15]
  Lin, C. H.; Yuan, J. J.; Liu, D. Y.; Zhang, H. F.; Xu, Z. H. Chin. J. Org. Chem. 2017, 37, 1560(in Chinese).
16. [16]
  Tahmassebi, W. D.; Wilson, L. J. A.; Kieser, J. M. Synth. Commun. 2009, 39, 2605. doi: 10.1080/00397910802663345
17. [17]
  Pesyan, N. N.; Gharib, A.; Behroozi, M.; Shokr, A. Arabian J. Chem. 2013, 5, 1.
18. [18]
  Rao, P. S.; Venkataratnam, R. V. Indian J. Chem. B. 1993, 32B, 484.
19. [19]
  Tahmassebi, D.; Wilson, L. J. A.; Kieser, J. M. Synth. Commun. 2009, 40, 260.
20. [20]
  Zhou, Z. H.; Yang, J.; Li, M. H.; Gu, Y. L. Green Chem. 2011, 13, 2204. doi: 10.1039/c1gc15411g
21. [21]
  Li, B. H.; Li, P. H.; Fang, X. N.; Li, C. X.; Sun, J. L.; Mo, L. P. Tetrahedron 2013, 69, 1057. doi: 10.1016/j.tet.2012.11.076
22. [22]
  Yan, N.; Xia, J. H.; Xiong, Y. K.; Xiong, B.; Lin, C. H.; Liao, W. L. Chin. J. Org. Chem. 2014, 34, 2487(in Chinese).
23. [23]
  Xu, Z. H.; Zhou, P.; Tu, Y. H.; Liu, D. Y.; Liao, W. L.; Liao, C. W. Heterocycles 2017, 94, 1115. doi: 10.3987/COM-17-13673
24. [24]
  Lars, K.; Joachim, T. J. Carbohydr. Chem. 2003, 22, 9. doi: 10.1081/CAR-120019010
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