Citation: Ye Ziping, Yang Jinhui, Feng Yao, Ma Tao, Niu Mingjie. First Enantioselective Synthesis of Brosimacutins H and I[J]. Chinese Journal of Organic Chemistry, ;2016, 36(3): 547-554. doi: 10.6023/cjoc201508021 shu

First Enantioselective Synthesis of Brosimacutins H and I

1.
State Key Laboratory Cultivation Base of Natural Gas Conversion, College of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021

Corresponding author: Yang Jinhui, yang_jh@nxu.edu.cn
Received Date: 24 August 2015
Revised Date: 6 November 2015

Fund Project: the Program for New Century Excellent Talents in University NCET-09-0860the National Natural Science Foundation of China 21362025

Figures(1)

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.
- brosimacutin,
- prenylated flavonoids,
- chalcone,
- dihydrochalcones,
- total synthesis
1. [1]
  Andersen, Ø. M.; Markham, K. R. Flavonoids, Chemistry, Biochemistry and Applications, Taylor & Francis, London, 2006.
2. [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. doi: 10.1021/jm040770b
3. [3]
  Meragelman, T. L.; Tucker, K. D.; McClord, T. G.; Cardel-lina, J. H.; Shoemker, R. H. J. Nat. Prod. 2005, 68, 1790. doi: 10.1021/np0503000
4. [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. doi: 10.1021/np0601861
5. [5]
  Prestos, C.; Boziaris, I. S.; Nychas, J. E. Food Chem. 2005, 93, 1998.
6. [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. doi: 10.1016/j.bmcl.2012.10.130
7. [7]
  Tamotsu, N.; Taichi, O.; Takeshi, K. Chem. Pharm. Bull. 1989, 37, 1392. doi: 10.1248/cpb.37.1392
8. [8]
  Barron, D.; Ibraham, R. K. Phytochemistry 1996, 43, 921. doi: 10.1016/S0031-9422(96)00344-5
9. [9]
  Takashima, J.; Ohsaki, A. J. Nat. Prod. 2002, 65, 1483.
10. [10]
  Takashima, J.; Ohsaki, A. Planta Med. 2005, 71, 654. doi: 10.1055/s-2005-871272
11. [11]
  Feng, Y.; Yang, J. H.; Ma, X. Q.; Cheng, B. B.; Xie, Y. M. Chin. J. Org. Chem. 2014, 34, 2015 (in Chinese). doi: 10.6023/cjoc201406018
12. [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). doi: 10.6023/cjoc201210016
13. [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. doi: 10.1016/j.cclet.2011.11.015
14. [14]
  Yang, J. H.; Chen, B. B.; Xie, Y. M.; Feng, Y.; Ma, X. Q. Chin. Chem. Lett. 2013, 24, 1027. doi: 10.1016/j.cclet.2013.07.007
15. [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).
16. [16]
  Ma, X. Q.; Yang, J. H.; Feng, Y.; Cheng, B. B.; Xie, Y. M. Chin. J. Org. Chem. 2014, 34, 2001 (in Chinese). doi: 10.6023/cjoc201407047
17. [17]
  Fristrup, P.; Jensen, G. H.; Andersen, M. L. N.; Tanner, D.; Norrby, P. O. J. Organomet. Chem. 2006, 2182.
1. [1]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001
2. [2]
  Yurong Tang , Yunren Shi , Yi Xu , Bo Qin , Yanqin Xu , Yunfei Cai . Innovative Experiment and Course Transformation Practice of Visible-Light-Mediated Photocatalytic Synthesis of Isoquinolinone. University Chemistry, 2024, 39(5): 296-306. doi: 10.3866/PKU.DXHX202311087
3. [3]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
4. [4]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
5. [5]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
6. [6]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
7. [7]
  Huijuan Liao , Yulin Xiao , Dong Xue , Mingyu Yang , Jianyang Dong . Synthesis of 1-Benzyl Isoquinoline via the Minisci Reaction. University Chemistry, 2025, 40(7): 294-299. doi: 10.12461/PKU.DXHX202409092
8. [8]
  Guojie Xu , Fang Yu , Yunxia Wang , Meng Sun . Introduction to Metal-Catalyzed β-Carbon Elimination Reaction of Cyclopropenones. University Chemistry, 2024, 39(8): 169-173. doi: 10.3866/PKU.DXHX202401060
9. [9]
  Wei Li , Jinfan Xu , Yongjun Zhang , Ying Guan . 共价有机框架整体材料的制备及食品安全非靶向筛查应用——推荐一个仪器分析综合化学实验. University Chemistry, 2025, 40(6): 276-285. doi: 10.12461/PKU.DXHX202406013
10. [10]
  Linjie ZHU , Xufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416
11. [11]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
12. [12]
  Zian Lin , Yingxue Jin . Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry (MALDI-MS) for Disease Marker Screening and Identification: A Comprehensive Experiment Teaching Reform in Instrumental Analysis. University Chemistry, 2024, 39(11): 327-334. doi: 10.12461/PKU.DXHX202403066
13. [13]
  Yifeng TAN , Ping CAO , Kai MA , Jingtong LI , Yuheng WANG . Synthesis of pentaerythritol tetra(2-ethylthylhexoate) catalyzed by h-MoO₃/SiO₂. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2155-2162. doi: 10.11862/CJIC.20240147
14. [14]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
15. [15]
  Yuhao SUN , Qingzhe DONG , Lei ZHAO , Xiaodan JIANG , Hailing GUO , Xianglong MENG , Yongmei GUO . Synthesis and antibacterial properties of silver-loaded sod-based zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 761-770. doi: 10.11862/CJIC.20230169
16. [16]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-. doi: 10.3866/PKU.WHXB202309027
17. [17]
  Yinwu Su , Xuanwen Zheng , Jianghui Du , Boda Li , Tao Wang , Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092
18. [18]
  Min LIU , Huapeng RUAN , Zhongtao FENG , Xue DONG , Haiyan CUI , Xinping WANG . Neutral boron-containing radical dimers. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 123-130. doi: 10.11862/CJIC.20240362
19. [19]
  Xiao SANG , Qi LIU , Jianping LANG . Synthesis, structure, and fluorescence properties of Zn(Ⅱ) coordination polymers containing tetra-alkenylpyridine ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2124-2132. doi: 10.11862/CJIC.20240158
20. [20]
  Hongjie SHEN , Haozhe MIAO , Yuhe YANG , Yinghua LI , Deguang HUANG , Xiaofeng ZHANG . Synthesis, crystal structure, and fluorescence properties of two Cu(Ⅰ) complexes based on pyridyl ligand. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 855-863. doi: 10.11862/CJIC.20250009

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(964)
HTML views(118)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142