Citation: Meng Jin, Du Liyue, Guo Liucheng. Synthesis of Arylnaphthalene Lignan Lactones[J]. Chinese Journal of Organic Chemistry, ;2016, 36(11): 2723-2728. doi: 10.6023/cjoc201603007 shu

Synthesis of Arylnaphthalene Lignan Lactones

1.
Department of Pharmacy, Luohe Medical College, Luohe, Henan 462002

Corresponding author: Meng Jin, mz_511310@163.com
Received Date: 6 March 2016
Revised Date: 21 July 2016

Figures(4)

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. In this study, a convenient method is presented for the multiple parallel synthesis of arylnaphthalene lignans. With vanillic acid as starting material, six arylnaphthalene nature products were prepared in the process with 8 steps, via Diels-Alder reaction, Suzuki reaction and Fetizon oxidation as the key reactions.
- Arylnaphthalene lignan lactones,
- Diels-Alder reaction,
- Suzuki-Miyaura coupling,
- Fetizon oxidation
1. [1]
  Apers, S.; Vlietinck, A.; Pieters, L. Phytochem. Rev. 2004, 2, 201.
2. [2]
  Ukita, T.; Nakamura, Y.; Kubo, A.; Yamamoto, Y.; Takahashi, M.; Kotera, J.; Ikeo, T. J. Med. Chem. 1999, 42, 1293. doi: 10.1021/jm9807048
3. [3]
  Ducharme, Y.; Brideau, C.; Dube, D.; Chan, C. C.; Falgueyret, J. P.; Gillard, J. W.; Guay, J.; Hutchinson, J. H.; McFarlane, C. S.; Riendeau, D. J. Med. Chem. 1994, 37, 512. doi: 10.1021/jm00030a010
4. [4]
  Kawazoe, K.; Yutani, A.; Tamemoto, K.; Yuasa, S.; Shibata, H.; Higuti, T.; Takaishi, Y. J. Nat. Prod. 2001, 64, 588. doi: 10.1021/np000307b
5. [5]
  Asano, J.; Chiba, K.; Tada, M.; Yoshii, T. Phytochemistry 1996, 42, 713. doi: 10.1016/0031-9422(96)00024-6
6. [6]
  Kang, K.; Oh, S. H.; Yun, J. H.; Jho, E. H.; Kang, J. H.; Batsuren, D.; Tunsag, J.; Park, K. H.; Kim, M.; Nho, C. W. Neoplasia 2011, 13, 1043. doi: 10.1593/neo.11972
7. [7]
  Baba, A.; Oda, T.; Taketomi, S.; Notoya, K.; Nishimura, A.; Makino, H.; Sohda, T. Chem. Pharm. Bull. 1999, 47, 369. doi: 10.1248/cpb.47.369
8. [8]
  Chang, C. W.; Lin, M. T.; Lee, S. S.; Liu, K. C. S. C.; Hsu, F. L.; Lin, J. Y. Antiviral Res. 1995, 27, 367. doi: 10.1016/0166-3542(95)00020-M
9. [9]
  Plaumann, H. P.; Smith, J. G.; Rodrigo, R. J. Chem. Soc., Chem Commun. 1980, 354.
  (b) Epsztajn, J.; Jozwiak, A.; Szczesniak, A. K. Tetrahedron 1993, 49, 929.
10. [10]
  Flanagan, S. R.; Harrowven, D. C.; Bradley, M. Tetrahedron 2002, 58, 5989.
  (b) Harrowven, D. C.; Bradley, M.; Lois Castro, J.; Flanagan, S. R. Tetrahedron Lett. 2001, 42, 6973.
11. [11]
  Ogiku, T.; Yoshida, S. I.; Kuroda, T.; Ohmizu, H.; Iwasaki, T. Synlett 1992, 651.
  (b) Ogiku, T.; Yoshida, S. I.; Ohmizu, H.; Iwasaki, T. J. Org. Chem. 1995, 60, 4585.
12. [12]
  Meyers, A.; Avila, W. B. J. Org. Chem. 1981, 46, 3881.
  (b) Hattori, T.; Suzuki, M.; Komuro, Y.; Miyano, S. J. Chem. Soc., Perkin. Trans. 1 1995, 235.
  (c) Hattori, T.; Suzuki, M.; Komuro, Y.; Miyano, S. J. Chem. Soc., Perkin. Trans. 1 1995, 1473.
13. [13]
  Anastas, P. T.; Stevenson, R. J. Nat. Prod. 1991, 54, 1687.
  (b) Stevenson, R. Weber, J. V. J. Nat. Prod. 1991, 54, 310.
14. [14]
  Tang, J. S.; Zheng, M. Chem. Reag. 2011, 10, 29 (in Chinese).
15. [15]
  Park, J. E.; Lee, J.; Seo, S. Y.; Shin, D. Tetrahedron Lett. 2014, 55, 818.
  (b) Kocsis, L. S.; Brummond, K. M. Org. lett. 2014, 16, 4158.
16. [16]
  He, Y.; Zhang, X. Y.; Fan, X. S. Chem. Commun. 2014, 50, 5641. doi: 10.1039/c4cc01738b
17. [17]
  Hayat, F.; Kang, L.; Lee, C. Y.; Shin, D. Tetrahedron 2015, 71, 2945. doi: 10.1016/j.tet.2015.03.023
18. [18]
  Patel, R. M.; Argade, N. P. Org. lett. 2012, 15, 14.
19. [19]
  Gudla, V.; Balamurugan, R. J. Org. Chem. 2011, 76, 9919. doi: 10.1021/jo201918d
20. [20]
  Harig, M.; Neumann, B.; Stammler, H. G.; Kuck, D. Eur. J. Org. Chem. 2004, 2004, 2381. doi: 10.1002/(ISSN)1099-0690
21. [21]
  Winterfeldt, E. Synthesis 1975, 617.
22. [22]
  Keay, B. A.; Lee, D. K. W.; Rodrigo, R. Tetrahedron Lett. 1980, 21, 3663. doi: 10.1016/S0040-4039(00)78738-7
23. [23]
  King, W.; Penprase, W. G.; Kloetzel, M. C. J. Org. Chem. 1961, 26, 3558.
  (b) Fetizon, M.; Golfier, M. C. R. Acad. Sci., Paris, Ser. C 1968, 267, 900.
24. [24]
  Blair, J.; Newbold, G. T. J. Chem. Soc. 1954, 1836. doi: 10.1039/jr9540001836
1. [1]
  Yiying Yang , Dongju Zhang . Elucidating the Concepts of Thermodynamic Control and Kinetic Control in Chemical Reactions through Theoretical Chemistry Calculations: A Computational Chemistry Experiment on the Diels-Alder Reaction. University Chemistry, 2024, 39(3): 327-335. doi: 10.3866/PKU.DXHX202309074
2. [2]
  Ling Fan , Meili Pang , Yeyun Zhang , Yanmei Wang , Zhenfeng Shang . Quantum Chemistry Calculation Research on the Diels-Alder Reaction of Anthracene and Maleic Anhydride: Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(4): 133-139. doi: 10.3866/PKU.DXHX202309024
3. [3]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
4. [4]
  Yu-Hang Miao , Zheng-Xu Zhang , Xu-Yi Huang , Yuan-Zhao Hua , Shi-Kun Jia , Xiao Xiao , Min-Can Wang , Li-Ping Xu , Guang-Jian Mei . Catalytic asymmetric dearomative azo-Diels–Alder reaction of 2-vinlyindoles. Chinese Chemical Letters, 2024, 35(4): 108830-. doi: 10.1016/j.cclet.2023.108830
5. [5]
  Chuanming GUO , Kaiyang ZHANG , Yun WU , Rui YAO , Qiang ZHAO , Jinping LI , Guang LIU . Performance of MnO₂-0.39IrO_x composite oxides for water oxidation reaction in acidic media. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1135-1142. doi: 10.11862/CJIC.20230459
6. [6]
  Tong Zhou , Jun Li , Zitian Wen , Yitian Chen , Hailing Li , Zhonghong Gao , Wenyun Wang , Fang Liu , Qing Feng , Zhen Li , Jinyi Yang , Min Liu , Wei Qi . Experiment Improvement of “Redox Reaction and Electrode Potential” Based on the New Medical Concept. University Chemistry, 2024, 39(8): 276-281. doi: 10.3866/PKU.DXHX202401005
7. [7]
  Ji-Quan Liu , Huilin Guo , Ying Yang , Xiaohui Guo . Calculation and Discussion of Electrode Potentials in Redox Reactions of Water. University Chemistry, 2024, 39(8): 351-358. doi: 10.3866/PKU.DXHX202401031
8. [8]
  Zhuoyan Lv , Yangming Ding , Leilei Kang , Lin Li , Xiao Yan Liu , Aiqin Wang , Tao Zhang . Light-Enhanced Direct Epoxidation of Propylene by Molecular Oxygen over CuO_x/TiO₂ Catalyst. Acta Physico-Chimica Sinica, 2025, 41(4): 100038-. doi: 10.3866/PKU.WHXB202408015
9. [9]
  Zhenxing Liu , Jiaen Hu , Zishi Cheng , Xinqi Hao . 基础有机化学教学中烯烃的氧化反应. University Chemistry, 2025, 40(6): 139-144. doi: 10.12461/PKU.DXHX202408107
10. [10]
  Yi Yang , Xin Zhou , Miaoli Gu , Bei Cheng , Zhen Wu , Jianjun Zhang . Femtosecond transient absorption spectroscopy investigation on ultrafast electron transfer in S-scheme ZnO/CdIn₂S₄ photocatalyst for H₂O₂ production and benzylamine oxidation. Acta Physico-Chimica Sinica, 2025, 41(6): 100064-. doi: 10.1016/j.actphy.2025.100064
11. [11]
  Yu Dai , Xueting Sun , Haoyu Wu , Naizhu Li , Guoe Cheng , Xiaojin Zhang , Fan Xia . Determination of the Michaelis Constant for Gold Nanozyme-Catalyzed Decomposition of Hydrogen Peroxide. University Chemistry, 2025, 40(5): 351-356. doi: 10.12461/PKU.DXHX202407052
12. [12]
  Chunmei GUO , Weihan YIN , Jingyi SHI , Jianhang ZHAO , Ying CHEN , Quli FAN . Facile construction and peroxidase-like activity of single-atom platinum nanozyme. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1633-1639. doi: 10.11862/CJIC.20240162
13. [13]
  Endong YANG , Haoze TIAN , Ke ZHANG , Yongbing LOU . Efficient oxygen evolution reaction of CuCo₂O₄/NiFe-layered bimetallic hydroxide core-shell nanoflower sphere arrays. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 930-940. doi: 10.11862/CJIC.20230369
14. [14]
  Lisha LEI , Wei YONG , Yiting CHENG , Yibo WANG , Wenchao HUANG , Junhuan ZHAO , Zhongjie ZHAI , Yangbin DING . Application of regenerated cellulose and reduced graphene oxide film in synergistic power generation from moisture electricity generation and Mg-air batteries. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1151-1161. doi: 10.11862/CJIC.20240202
15. [15]
  Guowen Xing , Guangjian Liu , Le Chang . Five Types of Reactions of Carbonyl Oxonium Intermediates in University Organic Chemistry Teaching. University Chemistry, 2025, 40(4): 282-290. doi: 10.12461/PKU.DXHX202407058
16. [16]
  Tingbo Wang , Yao Luo , Bingyan Hu , Ruiyuan Liu , Jing Miao , Huizhe Lu . Quantitative Computational Study on the Claisen Rearrangement Reaction of Allyl Phenyl Ethers: An Introduction to a Computational Chemistry Experiment. University Chemistry, 2024, 39(11): 278-285. doi: 10.12461/PKU.DXHX202403082
17. [17]
  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
18. [18]
  Lina Guo , Ruizhe Li , Chuang Sun , Xiaoli Luo , Yiqiu Shi , Hong Yuan , Shuxin Ouyang , Tierui Zhang . 层状双金属氢氧化物的层间阴离子对衍生的Ni-Al₂O₃催化剂光热催化CO₂甲烷化反应的影响. Acta Physico-Chimica Sinica, 2025, 41(1): 2309002-. doi: 10.3866/PKU.WHXB202309002
19. [19]
  Rong Tian , Yadi Yang , Naihao Lu . Comprehensive Experimental Design of Undergraduate Students Based on Interdisciplinarity: Study on the Effect of Quercetin on Chlorination Activity of Myeloperoxidase. University Chemistry, 2024, 39(8): 247-254. doi: 10.3866/PKU.DXHX202312064
20. [20]
  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

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1246)
HTML views(173)

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