SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 12: 2276 - 2282

DOI: https://doi.org/10.6023/cjoc201210016

Articles

Study on Total Synthesis of Four Natural Prenylated Flavonoids

  • Zuo Wubiao ,
  • Yang Jinhui ,
  • Li Hongjun ,
  • Guo Dongdong ,
  • Luo Junshan ,
  • Huang Wenqian
Expand
  • State Key Laboratory Cultivation Base of Natural Gas Conversion, Ningxia University, Yinchuan 750021

Received date: 2012-10-13

  Revised date: 2012-10-31

  Online published: 2012-11-02

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21162021, 20962016), the Ningxia Natural Science Foundation (No. NZ1006), the Program for New Century Excellent Talents in University (No. NCET-09-0860) and the National Basic Research Program 973 of China (No. 2010CB534916).

Fold

Abstract

A facile approach for the total synthesis of prenylated flavonoids, (?)-abyssinone-VI-4-O-methyl ether (1), (?)-abyssinone-IV-4'-O-methyl ether (2), (?)-abyssinone-V-4'-O-methyl ether (3) and (?)-sigmoidin E (4), has been described. The key intermediate 4-hydroxy-3,5-di-(3-methylbut-2-enyl)benzaldehyde (6) was synthesized that features regioselective prenylation of 4-hydroxybenzaldehyde and crystallizing with petroleum ether from the reaction mixture by freeze-out effect. All structures of new compounds were confirmed by IR, 1H NMR, MS and HRMS techniques.

Key words： prenylated flavonoind; (?)-abyssinone-VI-4-O-methyl ether; (?)-abyssinone-IV-4'-O-methyl ether; (?)- abyssinone-V-4'-O-methyl ether; (?)-sigmoidin E; total synthesis

Cite this article

Zuo Wubiao , Yang Jinhui , Li Hongjun , Guo Dongdong , Luo Junshan , Huang Wenqian . Study on Total Synthesis of Four Natural Prenylated Flavonoids[J]. Chinese Journal of Organic Chemistry, 2012 , 32(12) : 2276 -2282 . DOI: 10.6023/cjoc201210016

References

[1] Salvatore, M. J.; Kng, A. B.; Graham A. C.; Onishi, H. R.; Bartizal, K. F.; Abruzzo, G. K.; Gill, C. J.; Ramjit, H. G.; Pitzenberger, S. M.; Witherup, K. M. J. Nat. Prod. 1998, 61, 640.

[2] Rahman, M. M.; Gray, A. I.; Khondkar, P.; Sarker, S. D. Pharm. Biol. 2008, 46, 356.

[3] Meragelman, T. L.; Tucker, K. D.; McClord, T. G.; Cardel-lina, J. H.; Shoemker, R. H. J. Nat. Prod. 2005, 68, 1790.

[4] Hirpara, K. V.; Aggarwal, P.; Mukherjee, A. J.; Joshi, N.; Burman, A. C. Curr. Med. Chem. 2009, 9, 138.

[5] Seshadri, T. R. Tetrahedron 1959, 6, 169.

[6] Yan, X.; Liu, H. Q.; Zou, Y. Q.; Ren, Z. H. Chin. J. Org. Chem. 2008, 28, 1534 (in Chinese).(延玺, 刘会青, 邹永青, 任占华, 有机化学, 2008, 28, 1534.)

[7] Oliver-Bever, B. Medicinal Plants in Tropical West Africa, Cambridge University Press, New York, 1981, p. 100.

[8] Na, M.; Jang, J.; Njamen, D.; Mbafor, J. T.; Fomum, Z. T.; Kim, B. Y.; Oh, W. K.; Ahn, J. S. J. Nat. Prod. 2006, 69, 1572.

[9] Moriyasu, M.; Ichimaru, M.; Nishiyama, Y.; Kato, A.; Mathenge, S. G; Juma, F. D.; Nganga, J. N. J. Nat. Prod. 1998, 61, 185.

[10] Yenesew, A.; Midiwo, J. O.; Miessner, M.; Heydenreich, M.; Peter, M. G. Phytochemistry 1998, 48, 1439.

[11] Promsattha, R.; Tempesta, M. S.; Fomum, Z. T.; Mbafor, J. T. J. Nat. Prod. 1988, 51, 611.

[12] Zhang, Y. H.; Yang, J. H.; Li, H. J.; Jiang, S. Z.; Li, Y. F.; Liu, W. Y. Chin. J. Chem. 2011, 29, 521.

[13] Yang, J. H.; Li, H. J.; Zhang, Y. H.; Jiang, S. Z.; Li, Y. F.; Xue, P.; Ma, Y. L.; Liu, W. Y. Chin. J. Org. Chem. 2011, 31, 1230 (in Chinese).(杨金会, 李红俊, 张玉恒, 江世智, 李云峰, 薛屏, 马玉龙, 刘万毅, 有机化学, 2011, 31, 1230.)

[14] Yang, J. H.; Luo, J. S.; Guo, D. D.; Huang, W. Q. Chin. J. Org. Chem. 2012, 32, 1749 (in Chinese).(杨金会, 落俊山, 郭冬冬, 黄文倩, 有机化学, 2012, 32, 1749.)

[15] Farmer, R. L.; Biddle, M. M.; Nibbs, A. E.; Huang, X. K.; Bergan, R. C.; Scheidt, K. A. ACS Med. Chem. Lett. 2010, 1, 400.

[16] Kazuaki, k.; Katsuo, H.; Sadakazu, Y.; Teruya, S.; Ichiro, T. S. Agric. Biol. Chem. 1975, 39, 133.

Options
Outlines

/

〈 〉