First Enantioselective Synthesis of Brosimacutins H and I

doi:10.6023/cjoc201508021

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (3): 547-554.DOI: 10.6023/cjoc201508021 Previous Articles Next Articles

Articles

天然产物BrosimacutinsH和I的对映选择性全合成

叶子平, 杨金会, 冯尧, 马涛, 牛明杰

宁夏大学化学化工学院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:2015-08-24 修回日期:2015-11-06 发布日期:2015-11-26
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. 21362025)、教育部"新世纪优秀人才支持计划"(No. NCET-09-0860)资助项目.

First Enantioselective Synthesis of Brosimacutins H and I

Ye Ziping, Yang Jinhui, Feng Yao, Ma Tao, Niu Mingjie

State Key Laboratory Cultivation Base of Natural Gas Conversion, College of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021

Received:2015-08-24 Revised:2015-11-06 Published:2015-11-26
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21362025) and the Program for New Century Excellent Talents in University (No. NCET-09-0860) .

1. First Enantioselective Synthesis of Brosimacutins H and I.PDF(3805KB)

Abstract

Brosimacutins H and I, isolated from the bark of brosimum acutifolium huber, are flavanoid compounds with similar structures. The bark of this plant is used in Brazilian folk medicine as an anti-inflammatory and anti-rheumatic agent, and cellular activities were reported for these two compounds. Herein the first enantio-selective synthesis of brosimacutins H and I from cheap starting material hydroxyl-acetophenone and hydroxyl benzene formaldehyde was reported. All new compounds in this study were confirmed by NMR and HRMS.

Key words: brosimacutin, prenylated flavonoids, chalcone, dihydrochalcones, total synthesis

Cite this article

Ye Ziping, Yang Jinhui, Feng Yao, Ma Tao, Niu Mingjie. First Enantioselective Synthesis of Brosimacutins H and I[J]. Chin. J. Org. Chem., 2016, 36(3): 547-554.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Andersen, Ø. M.; Markham, K. R. Flavonoids, Chemistry, Biochemistry and Applications, Taylor & Francis, London, 2006.
[2] Daskiewicz, J. B.; Depeint, F.; Viornery, L.; Bayet, C.; Comte-Sarrazin, G.; Comte, G.; Gee, J. M.; Johnson, I. T.; Ndjoko, K. K.; Hostettmann, K.; Barron, D. J. Med. Chem. 2005, 48, 2790.
[3] Meragelman, T. L.; Tucker, K. D.; McClord, T. G.; Cardel-lina, J. H.; Shoemker, R. H. J. Nat. Prod. 2005, 68, 1790.
[4] 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.
[5] Prestos, C.; Boziaris, I. S.; Nychas, J. E. Food Chem. 2005, 93, 1998.
[6] Yoon, H.; Kim, T. W.; Shin, S. Y.; Park, M. J.; Yong, Y.; Kim, D. W.; Islam, T.; Lee, Y. H.; Jung, K. Y.; Lim, Y. Biol. Med. Chem. Lett. 2013, 23, 232.
[7] Tamotsu, N.; Taichi, O.; Takeshi, K. Chem. Pharm. Bull. 1989, 37, 1392.
[8] Barron, D.; Ibraham, R. K. Phytochemistry 1996, 43, 921.
[9] Takashima, J.; Ohsaki, A. J. Nat. Prod. 2002, 65, 1483.
[10] Takashima, J.; Ohsaki, A. Planta Med. 2005, 71, 654.
[11] Feng, Y.; Yang, J. H.; Ma, X. Q.; Cheng, B. B.; Xie, Y. M. Chin. J. Org. Chem. 2014, 34, 2015 (in Chinese). (冯尧, 杨金会, 马晓琴, 陈兵兵, 谢一民, 有机化学, 2014, 34, 2015.)
[12] Zuo, W. B.; Yang, J. H.; Li, H. J.; Guo, D. D.; Luo, J. S.; Huang, W. Q. Chin. J. Org. Chem. 2012, 32, 2276 (in Chinese). (左武标, 杨金会, 李红俊, 郭冬冬, 落俊山, 黄文倩, 有机化学, 2012, 32, 2276.)
[13] Yang, J. H.; Huang, W. Q.; Luo, J. S.; Guo, D. D.; Zhang, Y. H.; Li, H. J. Chin. Chem. Lett. 2012, 23, 127.
[14] Yang, J. H.; Chen, B. B.; Xie, Y. M.; Feng, Y.; Ma, X. Q. Chin. Chem. Lett. 2013, 24, 1027.
[15] Yang, J. H.; Xie, Y. M.; Feng, S. B.; Zuo, W. B.; Cheng, B. B.; Ma, X. Q.; Feng, Y. Chin. J. Org. Chem. 2012, 32, 2159 (in Chinese). (杨金会, 谢一民, 冯尚彪, 左武标, 陈兵兵, 马晓琴, 冯尧, 有机化学, 2012, 32, 2159.)
[16] Ma, X. Q.; Yang, J. H.; Feng, Y.; Cheng, B. B.; Xie, Y. M. Chin. J. Org. Chem. 2014, 34, 2001 (in Chinese). (马晓琴, 杨金会, 冯尧, 陈兵兵, 谢一民, 有机化学, 2014, 34, 2001.)
[17] Fristrup, P.; Jensen, G. H.; Andersen, M. L. N.; Tanner, D.; Norrby, P. O. J. Organomet. Chem. 2006, 2182.

天然产物BrosimacutinsH和I的对映选择性全合成

First Enantioselective Synthesis of Brosimacutins H and I

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Ran Zhou, Chunmei Yuan, Tao Zhang, Piao Mao, Yi Liu, Kaini Meng, Hui Xin, Wei Xue. Design, Synthesis and Bioactivity of Chalcone Derivative Containing Quinazolinone [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3196-3209.
[2]	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.
[3]	Duoduo Tang, Danfeng Huang, Kehu Wang, Hu Ma, Yang Feng, Yuanyuan Ren, Junjiao Wang, Yulai Hu. Tin Powder-Promoted Synthesis of 1,3-Disubstituted 1,3-Dihydroisobenzofuran Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4227-4238.
[4]	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.
[5]	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.
[6]	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.
[7]	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.
[8]	Xin Liu, Runmei Xu, Lin Wang, Yaxue Liu, Zhihao Chen, Wei Qin, Yushun Tian. Synthesis and Evaluation in vitro of Dihydrothiophenopyridine-Chalcone Derivatives as Anticancer Activity Agents [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3550-3559.
[9]	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.
[10]	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.
[11]	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.
[12]	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.
[13]	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.
[14]	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.
[15]	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.