Citation: Chen Wang, Hu Daihua, Feng Zili, Lin Mingyu, Han Meng. Progress in Synthesis of α-Arylnaphthalene Lignan Lactones[J]. Chemistry, ;2018, 81(4): 303-311. shu

Progress in Synthesis of α-Arylnaphthalene Lignan Lactones

Vitamin D Research Institute, Shaanxi University of Technology, Hanzhong 723001

Corresponding author: Chen Wang, chenwang0519@126.com
Received Date: 27 November 2017
Accepted Date: 22 January 2018

Figures(1)

Arylnaphthalene lignan lactones, widely distributed in plants, are a class of natural products containing the phenyl-naphthyl skeleton. These compounds have attracted considerable attention of many scientists for decades because of their wide biological activities. This article reviews the recent progress in chemical synthesis of α-arylnaphthalene lignan lactones since 1980, aiming to provide references for the syntheses and clinical development of α-arylnaphthalene lignan lactones.
- α-Arylnaphthalene lignan lactones,
- Analogues,
- Synthesis
1. [1]
  R B Teponno, S Kusari, M Spiteller. Nat. Prod. Res., 2016, 33(9):1044~1092.
2. [2]
  T Ukita, Y Nakamura, A Kubo et al. J. Med. Chem., 1999, 42(7):1293~1305.
3. [3]
  K Kawazoe, A Yutani, K Tamemoto et al. J. Nat. Prod., 2001, 64(5):588~591.
4. [4]
  D Janmanchi, C H Lin, J Y Hsieh et al. Bioorg. Med. Chem., 2013, 21(7):2163~2176.
5. [5]
  H J Zhang, E Rumschlag-Booms, Y F Guan et al. Phytochemistry, 2017, 136(Supplement C):94~100.
6. [6]
  (a) K Kang, S H Oh, J H Yun et al. Neoplasia, 2011, 13(11):1043~1057; (b) Y Ren, D D Lantvit, Y Deng et al. J. Nat. Prod., 2014, 77(6):1494~1504.
7. [7]
  J Luo, Y Hu, W Kong et al. PloS One, 2014, 9(3):e93516.
8. [8]
  S Hemmati, H Seradj. Molecules, 2016, 21(7):820~840.
9. [9]
  K S Sagar, C C Chang, W K Wang et al. Bioorg. Med. Chem., 2004, 12(15):4045~4054.
10. [10]
  J Y Pan, S L Chen, M H Yang et al. Nat. Prod. Res., 2009, 26(10):1251~1292.
11. [11]
  R Stevenson, J V Weber. J. Nat. Prod., 1989, 52(2):367~375.
12. [12]
  R Stevenson, J V Weber. J. Nat. Prod., 1991, 54(1):310~314.
13. [13]
  P T Anastas, R Stevenson. J. Nat. Prod., 1991, 54(6):1687~1691.
14. [14]
15. [15]
  T Kudoh, A Shishido, K Ikeda et al. Synlett, 2013, 24(12):1509~1512.
16. [16]
  S Mondal, M Maji, A Basak. Tetrahed. Lett., 2011, 52(11):1183~1186.
17. [17]
  L S Kocsis, K M Brummond. Org. Lett., 2014, 16(16):4158~4161.
18. [18]
  J E Park, J Lee, S Y Seo et al. Tetrahed. Lett., 2014, 55(4):818~820.
19. [19]
  (a) S O D Silva, C S Denis, R Rodrigo. Chem. Commun., 1980, 21(21):995~997; (b) H P Plaumann, J G Smith, R Rodrigo. Chem. Commun., 1980, 8(8):354~355.
20. [20]
  X Lu, M G Bi, S Wu et al. J. Asian Nat. Prod. Res., 2012, 14(4):322~326.
21. [21]
  J Hui, Z Yu, L Zhu. Med. Chem. Res., 2012, 21(12):3994~4001.
22. [22]
  J Epsztajn, A Jóźwiak, A K Szcześniak. Tetrahedron, 1993, 49(4):929~938.
23. [23]
  (a) J E Cochran, A Padwa. J. Org. Chem., 1995, 60(13):3938~3939; (b) A Padwa, J E Cochran, C O Kappe. J. Org. Chem., 1996, 61(11):3706~3714.
24. [24]
  A I Meyers, W B Avila. J. Org. Chem., 1981, 46(19):3881~3886.
25. [25]
  (a) T Hattori, H Tanaka, Y Okaishi et al. Chem. Commun., 1995, 26(3):235~241; (b) T Hattori, M Suzuki, Y Komuro et al. J. Chem. Soc., Perkin Transac., 1995, 12(12):1473~1474.
26. [26]
  Y He, X Y Zhang, X S Fan. Chem. Commun., 2014, 50(42):5641~5643.
27. [27]
  F Hayat, L Kang, C Y Lee et al. Tetrahedron, 2015, 71(19):2945~2950.
28. [28]
  D Mal, S Jana. J. Org. Chem., 2016, 81(23):11857~11865.
29. [29]
30. [30]
  Y Ishii, T Ikariya, M Saburi et al. Tetrahed. Lett., 1986, 27(3):365~368.
31. [31]
  T Kim, K H Jeong, K S Kang et al. Eur. J. Org. Chem., 2017, 2017(13):1704~1712.
32. [32]
  (a) T Ogiku, M Seki, M Takahashi et al. Tetrahed. Lett., 1990, 31(31):5487~5490; (b) T Ogiku, S I Yoshida, T Kuroda et al. Synlett, 1992, 1992(8):651~652.
33. [33]
  T Ogiku, S Yoshida, H Ohmizu et al. J. Org. Chem., 1995, 60(14):4585~4590.
34. [34]
  E Yoshida, D Yamashita, R Sakai et al. Synlett, 2010, (15):2275~2278.
35. [35]
  V Gudla, R Balamurugan. J. Org. Chem., 2011, 76(24):9919~9933.
36. [36]
  N Eghbali, J Eddy, P T Anastas. J. Org. Chem., 2008, 73(17):6932~6935.
37. [37]
  P Foley, N Eghbali, P T Anastas. Green. Chem., 2010, 12(5):888~892.
38. [38]
  P Foley, N Eghbali, P T Anastas. J. Nat. Prod., 2010, 73(5):811~813.
39. [39]
  G. Naresh, R Kant, T Narender. Org. Lett., 2015, 17(14):3446~3449.
40. [40]
  Y Sato, T Tamura, A Kinbara et al. Adv. Synth. Catal., 2007, 349(4/5):647~661.
41. [41]
  R M Patel, N P Argade. Org. Lett., 2013, 15(1):14~17.
42. [42]
  D C Harrowven, M Bradley, J L Castro et al. Tetrahed. Lett., 2001, 42(39):6973~6975.
43. [43]
  S R Flanagan, D C Harrowven, M Bradley. Tetrahedron, 2002, 58(30):5989~6001.
44. [44]
  S Takano, S Otaki, K Ogasawara. Tetrahed. Lett., 1985, 26(13):1659~1660.
45. [45]
  T T Kao, C C Lin, K S Shia. J. Org. Chem., 2015, 80(13):6708~6714.
1. [1]
  Yuheng Zhou . 大学课堂的色彩——探索过渡元素的美. University Chemistry, 2025, 40(6): 303-309. doi: 10.12461/PKU.DXHX202407110
2. [2]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
3. [3]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
4. [4]
  Qiaowen CHANG , Ke ZHANG , Guangying HUANG , Nuonan LI , Weiping LIU , Fuquan BAI , Caixian YAN , Yangyang FENG , Chuan ZUO . Syntheses, structures, and photo-physical properties of iridium phosphorescent complexes with phenylpyridine derivatives bearing different substituting groups. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 235-244. doi: 10.11862/CJIC.20240311
5. [5]
  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
6. [6]
  Renxiu Zhang , Xin Zhao , Yunfei Zhang . Application of Electrochemical Synthesis in the Teaching of Organic Chemistry. University Chemistry, 2025, 40(4): 174-180. doi: 10.12461/PKU.DXHX202406116
7. [7]
  Cun WANG , Shaohan XU , Yuqian ZHANG , Yaoyao ZHANG , Tao GONG , Rong WEN , Yuhang LIAO , Yanrong REN . Terbium complex electrochemiluminescent emitters: Synthesis and application in the detection of epinephrine. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1351-1360. doi: 10.11862/CJIC.20240427
8. [8]
  Fei Liu , Dong-Yang Zhao , Kai Sun , Ting-Ting Yu , Xin Wang . Comprehensive Experimental Design for Photochemical Synthesis, Analysis, and Characterization of Seleno-Containing Medium-Sized N-Heterocycles. University Chemistry, 2024, 39(3): 369-375. doi: 10.3866/PKU.DXHX202309047
9. [9]
  Tingting Yu , Si Chen , Lianglong Sun , Tongtong Shi , Kai Sun , Xin Wang . Comprehensive Experimental Design for the Photochemical Synthesis, Analysis, and Characterization of Difluoropyrroles. University Chemistry, 2024, 39(11): 196-203. doi: 10.3866/PKU.DXHX202401022
10. [10]
  Lutian Zhao , Yangge Guo , Liuxuan Luo , Xiaohui Yan , Shuiyun Shen , Junliang Zhang . Electrochemical Synthesis for Metallic Nanocrystal Electrocatalysts: Principle, Application and Challenge. Acta Physico-Chimica Sinica, 2024, 40(7): 2306029-0. doi: 10.3866/PKU.WHXB202306029
11. [11]
  Li Jiang , Changzheng Chen , Yang Su , Hao Song , Yanmao Dong , Yan Yuan , Li Li . Electrochemical Synthesis of Polyaniline and Its Anticorrosive Application: Improvement and Innovative Design of the “Chemical Synthesis of Polyaniline” Experiment. University Chemistry, 2024, 39(3): 336-344. doi: 10.3866/PKU.DXHX202309002
12. [12]
  Qilu DU , Li ZHAO , Peng NIE , Bo XU . Synthesis and characterization of osmium-germyl complexes stabilized by triphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1088-1094. doi: 10.11862/CJIC.20240006
13. [13]
  Hexing SONG , Zan SUN . Synthesis, crystal structure, Hirshfeld surface analysis, and fluorescent sensing for Fe³⁺ of an Mn(Ⅱ) complex based on 1-naphthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 885-892. doi: 10.11862/CJIC.20240402
14. [14]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
15. [15]
  Tao Cao , Fang Fang , Nianguang Li , Yinan Zhang , Qichen Zhan . Green Synthesis of p-Hydroxybenzonitrile Catalyzed by Spinach Extracts under Red-Light Irradiation: Research and Exploration of Innovative Experiments for Pharmacy Undergraduates. University Chemistry, 2024, 39(5): 63-69. doi: 10.3866/PKU.DXHX202309098
16. [16]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
17. [17]
  Cheng Zheng , Shiying Zheng , Yanping Zhang , Shoutian Zheng , Qiaohua Wei . Synthesis, Copper Content Analysis, and Luminescent Performance Study of Binuclear Copper (I) Complexes with Isomeric Luminescence Shift: A Comprehensive Chemical Experiment Recommendation. University Chemistry, 2024, 39(7): 322-329. doi: 10.3866/PKU.DXHX202310131
18. [18]
  Qianping Li , Hua Guan , Changfeng Wan , Yonghai Song , Jianwen Jiang . 大学有机化学复习课项目式教学——以“液晶化合物4-正戊基苯甲酸-4′-正戊基苯酯的合成路线设计与产品制备”为例. University Chemistry, 2025, 40(8): 100-116. doi: 10.12461/PKU.DXHX202410070
19. [19]
  Benhua Wang , Chaoyi Yao , Yiming Li , Qing Liu , Minhuan Lan , Guipeng Yu , Yiming Luo , Xiangzhi Song . 一种基于香豆素氟离子荧光探针的合成、表征及性能测试——“科研反哺教学”在有机化学综合实验教学中的探索与实践. University Chemistry, 2025, 40(6): 201-209. doi: 10.12461/PKU.DXHX202408070
20. [20]
  Hongyan Chen , Yajun Hou , Shui Hu , Zhuoxun Wei , Fang Zhu , Chengyong Su . Construction of Synthetic Chemistry Experiment of the Chemistry “101 Plan”. University Chemistry, 2024, 39(10): 58-63. doi: 10.12461/PKU.DXHX202409109

Get Citation

PDF

XML

Metrics

PDF Downloads(12)
Abstract views(2914)
HTML views(654)

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