Study on Total Synthesis of Four Natural Prenylated Flavonoids

doi:10.6023/cjoc201210016

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (12): 2276-2282.DOI: 10.6023/cjoc201210016 Previous Articles Next Articles

Articles

四个天然异戊烯基黄酮的全合成研究

左武标, 杨金会, 李红俊, 郭冬冬, 落俊山, 黄文倩

宁夏大学天然气转化国家重点实验室培育基地银川 750021

收稿日期:2012-10-13 修回日期:2012-10-31 发布日期:2012-11-02
通讯作者: 杨金会 E-mail:yang_jh@nxu.edu.cn
基金资助:
国家自然科学基金(Nos. 21162021, 20962016)、宁夏自然科学基金(No. NZ1006)、教育部“新世纪优秀人才支持计划资助”(No. NCET-09-0860)、国家重点基础研究发展计划(No. 2010CB534916)资助项目.

Study on Total Synthesis of Four Natural Prenylated Flavonoids

Zuo Wubiao, Yang Jinhui, Li Hongjun, Guo Dongdong, Luo Junshan, Huang Wenqian

State Key Laboratory Cultivation Base of Natural Gas Conversion, Ningxia University, Yinchuan 750021

Received:2012-10-13 Revised:2012-10-31 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).

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]. Chin. J. Org. Chem., 2012, 32(12): 2276-2282.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

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.

四个天然异戊烯基黄酮的全合成研究

Study on Total Synthesis of Four Natural Prenylated Flavonoids

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Xingzhou Liu, Mingjia Yu, Jianhua Liang. Research Progress on the Synthesis of Protoberberine Skeleton and Its Anti-inflammatory Activity [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1325-1340.
[2]	Jingping Hu, Wenqing Chen, Yuyang Jiang, Jing Xu. Synthesis of Tetracyclic Core Structure of Daphnezomines A and B [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 171-177.
[3]	Xiangkai Kong, Yipeng Zhang, Lingjing Dang, Wen Chen, Hongbin Zhang. Research Progress in Synthesis of Indole Alkaloids Vindoline and Vindorosine [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2728-2744.
[4]	Ran Gao, Weisheng Tian. Synthesis of Azedarachol and 2α,3α,20R-Trihydroxypregnane-16β-methacrylate [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2521-2526.
[5]	Mengmeng Xu, Quan Cai. Progress of Catalytic Asymmetric Diels-Alder Reactions of 2-Pyrones [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 698-713.
[6]	Jun Zhao, Jian Xiao, Yawen Wang, Yu Peng. Advances on the Synthesis of Natural Products with Dihydrobenzofuran Skeleton via Oxidative [3+2] Cycloadditions [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2933-2945.
[7]	Minxin Li, Qiuping Zou, Wenrong Du, Jinchun Gao, Yanping Li, Zewei Mao. Total Synthesis and Anti-inflammatory Evaluation of Dorsmerunin A [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3292-3296.
[8]	Jian Xiao, Yu Peng, Wei-Dong Z. Li. Advances on the Total Synthesis of Sesquiterpenoid Alkaloid Dendrobine [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2636-2649.
[9]	Xifei Yan, Jianfeng Zheng, Wei-Dong Z. Li. Studies on the Chemical Synthesis of Natural Drugs Berberine [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2217-2227.
[10]	Gang Yang, Xiangyu Feng, Congcong Han, Yang Chen, Shuzhong He. Synthesis of the ABC Ring System of Wallichanol Natural Product [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 726-730.
[11]	Ding Ma, Junli Ao, Naifeng Hu, Guangxin Liang. Progress in Biological Activity and Synthesis of Nematode Hatching Pheromone Glycinoeclepin A [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 553-566.
[12]	Lu Guo, Pingping Tang. Recent Advance in the Synthesis of Natural Products of Schisandra Triterpenoid [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3816-3825.
[13]	Han Jilai, Tang Meilin, Sun Xun. Study on the Total Synthesis of Resveratrol Dimers Quadrangularin A and Pallidol [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1571-1577.
[14]	Dong Wei, Wang Xin, Ge Zemei, He Fang, Li Runtao. Efficient Synthesis of Wogonin [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1725-1730.
[15]	Xie Tao, He Haibing, Gao Shuanhu. Synthetic Progress of Polycyclic Xanthone [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 551-562.