Synthetic Progress of Polycyclic Xanthone
- Corresponding author: He Haibing, hbhe@chem.ecnu.edu.cn Gao Shuanhu, shgao@chem.ecnu.edu.cn
Citation:
Xie Tao, He Haibing, Gao Shuanhu. Synthetic Progress of Polycyclic Xanthone[J]. Chinese Journal of Organic Chemistry,
;2020, 40(3): 551-562.
doi:
10.6023/cjoc201911007
Masters, K. S.; Brase, S. Chem. Rev. 2012, 112, 3717.
doi: 10.1021/cr100446h
(a) Cheng, G.; Sun, J.; Fridlender, Z. G.; Ching, L. C. S.; Wang, L. M.; Albelda, S. M. J. Biol. Chem. 2010, 285, 10553.
(b) Gobbi, S.; Zimmer, C.; Belluti, F.; Hartmann, R. W.; Rampa, A.; Recanatini, M.; Bisi, A. J. Med. Chem. 2010, 53, 5347.
(c) Palmeira, A.; Paiva, A.; Sousa, E.; Seca, H.; Almeida, G. M.; Lima, R. T.; Fernandezs, M. X.; Pinto, M.; Vasconcelos, M. H. Chem. Biol. Drug Des. 2010, 76, 43.
Honda, N. K.; Pavan, F. R.; Coelho, R. G.; Micheletti, A. C.; de Andrade Leite, S. R.; Lopes, T. I. B.; Beatriz, A.; Mitsutsu, M. Y.; Brum, R. L.; Leite, C. Q. F. Phytomedicine 2010, 17, 328.
doi: 10.1016/j.phymed.2009.07.018
Pinto, M. M.M.; Sousa, M. E.; Nascimento, M. S. Curr. Med. Chem. 2005, 12, 2517.
doi: 10.2174/092986705774370691
Lesch, B.; Bräse, S. Angew. Chem., Int. Ed. 2004, 43, 115.
doi: 10.1002/anie.200352154
Winter, D. K.; Sloman, D. L.; Porco, J. Nat. Prod. Rep. 2013, 30, 382.
doi: 10.1039/c3np20122h
Peoples, A. J.; Zhang, Q.; Millet, W. P.; Rothfeder, M. T.; Pescatore, B. C.; Madden, A. A.; Ling, L.; Moore, C. M. J. Antibiot. 2008, 61, 457.
doi: 10.1038/ja.2008.62
(a) Ratnayake, R.; Lacey, E.; Tennant, S.; Gill, J. H.; Capon, R. J. Org. Lett. 2006, 8, 5267.
(b) Ratnayake, R.; Lacey, E.; Tennant, S.; Gill, J. H.; Capon, R. J. Chem.-Eur. J. 2007, 13, 1610.
(a) Lee, T. M.; Carter, G. T.; Borders, D. B. J. Chem. Soc., Chem. Commun. 1989, 22, 1771.
(b) Korshalla, J.; Maiese, W. M.; Goodman, J.; Torrey, M. J.; Kantor, S.; Labeda, D. P.; Greenstein, M. J. Antibiot. 1990, 43, 1059.
Kunimoto, S.; Lu, J.; Esumi, H.; Yamazaki, Y.; Kinoshita, N.; Honma, Y.; Hamada, M.; Ohsono, M.; Ishizuka, M.; Takeuchi, T. J. Antibiot. 2003, 56, 1004.
doi: 10.7164/antibiotics.56.1004
Kunimoto, S.; Someno, T.; Yamazaki, Y.; Lu, J.; Esumi, H.; Naganawa, H. J. Antibiot. 2003, 56, 1012.
doi: 10.7164/antibiotics.56.1012
Terui, Y.; Chu, Y.; Li, J.-Y.; Ando, T.; Yamamoto, H.; Kawamura, Y.; Tomishima, Y.; Uchida, S.; Okazaki, T.; Munetomo, E.; Seki, T.; Yamamoto, K.; Murakami, S.; Kawashima, A. Tetrahedron Lett. 2003, 44, 5427.
doi: 10.1016/S0040-4039(03)01318-2
Qiao, Y.-F.; Okazaki, T.; Ando, T.; Mizoue, K.; Kondo, K.; Eguchi, T.; Kakinuma, K. J. Antibiot. 1998, 51, 282.
doi: 10.7164/antibiotics.51.282
Kondo, K.; Eguchi, T.; Kakinuma, K.; Mizoue, K.; Qiao, Y.-F. J. Antibiot. 1998, 51, 288.
doi: 10.7164/antibiotics.51.288
Malet-Cascon, L.; Romero, F.; Espliego-Vazquez, F.; Gravalos, D.; Fernandez-Puentes, J. L. J. Antibiot. 2003, 56, 219.
doi: 10.7164/antibiotics.56.219
Rodriguez, J. C.; Puentes, J. L. F.; Baz, J. P.; Canedo, L. M. J. Antibiot. 2003, 56, 318.
doi: 10.7164/antibiotics.56.318
Omura, S.; Iwai, Y.; Hinotozawa, K.; Takahashi, Y.; Kato, J.; Nakagawa, A.; Hirano, A.; Shimizu, H.; Haneda, K. J. Antibiot. 1982, 35, 645.
doi: 10.7164/antibiotics.35.645
Omura, S.; Nakagawa, A.; Kushida, K.; Lukacs, G. J. Am. Chem. Soc. 1986, 108, 6088.
doi: 10.1021/ja00279a095
Maiese, W. M.; Lechevalier, M. P.; Lechevalier, H. A.; Korshalla, J.; Goodman, J.; Wildey, M. J.; Kuck, N.; Greenstein, M. J. Antibiot. 1989, 42, 846.
doi: 10.7164/antibiotics.42.846
Carter, G. T.; Nietsche, J. A.; Williams, D. R.; Borders, D. B. J. Antibiot. 1990, 43, 504.
doi: 10.7164/antibiotics.43.504
Kelly, T. R.; Jagoe, C. T.; Li, Q. J. Am. Chem. Soc. 1989, 111, 4522.
doi: 10.1021/ja00194a071
(a) Rao, A. V. R.; Yadav, J. S.; Reddy, K. K.; V., U. Tetrahedron Lett. 1991, 32, 5199.
(b) Mehta, G.; Shah, S. R.; Venkateswarlu, Y. Tetrahedron 1994, 50, 11729.
Masuo, R.; Ohmori, K.; Hintermann, L.; Yoshida, S.; Suzuki, K. Angew. Chem., Int. Ed. 2009, 48, 3462.
doi: 10.1002/anie.200806338
Sloman, D. L.; Bacon, J. W.; Porco, J. A. J. Am. Chem. Soc. 2011, 133, 9952.
doi: 10.1021/ja203642n
Butler, J. R.; Wang, C.; Bian, J.; Ready, J. M. J. Am. Chem. Soc. 2011, 133, 9956.
doi: 10.1021/ja204040k
Wang, Y.; Wang, C.; Butler, J. R.; Ready, J. M. Angew. Chem., Int. Ed. 2013, 52, 10796.
doi: 10.1002/anie.201304812
Dai, Y.; Ma, F.; Shen, Y.; Xie, T.; Gao, S. Org. Lett. 2018, 20, 2872.
doi: 10.1021/acs.orglett.8b00901
(a) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525.
(b) Bringmann, G.; Mortimer, J. P.; Keller, P. A.; Gresser, M. J.; Garner, J.; Breuning, M. Angew. Chem., Int. Ed. 2005, 44, 5384.
Tamiya, M.; Ohmori, K.; Kitamura, M.; Kato, H.; Arai, T.; Oorui, M.; Suzuki, K. Chem.-Eur. J. 2007, 13, 9791.
doi: 10.1002/chem.200700863
(a) Karlsson, J. O.; Nguyen, N. V.; Foland, L. D.; Moore, H. W. J. Am. Chem. Soc. 1985, 107, 3392.
(b) Foland, L. D.; Karlsson, J. O.; Perri, S. T.; Schwabe, R.; Xu, S.; Patil, S.; Moore, H. W. J. Am. Chem. Soc. 1989, 111, 975.
Ratnayake, R.; Lacey, E.; Tennant, S.; Gill, J. H.; Capon, R. J. Org. Lett. 2006, 8, 5267.
doi: 10.1021/ol062113e
Winter, D. K.; Endoma-Arias, M. A.; Hudlicky, T.; Beutler, J. A.; Porco, J. A. J. Org. Chem. 2013, 78, 7617.
doi: 10.1021/jo401169z
Sloman, D. L.; Mitasev, B.; Scully, S. S.; Beutler, J. A.; Porco, J. A. Angew. Chem., Int. Ed. 2011, 50, 2511.
doi: 10.1002/anie.201007613
Endoma, M. A. A.; Bai, V. P.; Hansen, J.; Hudlicky, T. Org. Process Res. Dev. 2002, 6, 525.
doi: 10.1021/op020013s
(a) Liu, L.; Yang, B.; Katz, T. J.; Poindexter, M. K. J. Org. Chem. 1991, 56, 3769.
(b) Talele, H. R.; Gohil, J.; Bedekar, A. V. Bull. Chem. Soc. Jpn. 2009, 82, 1182.
Yang, J.; Knueppel, D.; Cheng, B.; Mans, D.; Martin, S. F. Org. Lett. 2015, 17, 114.
doi: 10.1021/ol503336t
Shi, Y. Acc. Chem. Res. 2004, 37, 488.
doi: 10.1021/ar030063x
Nicolaou, K. C.; Li, A. Angew. Chem., Int. Ed. 2008, 47, 6579.
doi: 10.1002/anie.200802632
(a) Li, X.; Hewgley, J. B.; Mulrooney, C. A.; Yang, J.; Kozlowski, M. C. J. Org. Chem. 2003, 68, 5500.
(b) Nakajima, M.; Miyoshi, I.; Kanayama, K.; Hashimoto, S.; Noji, M.; Koga, K. J. Org. Chem. 1999, 64, 2264.
Castillo-Contreras, E. B.; Dake, G. R. Org. Lett. 2014, 16, 1642.
doi: 10.1021/ol5002945
(a) Sakai, N.; Annaka, K.; Konakahara, T. J. Org. Chem. 2006, 71, 3653.
(b) Bianchi, G.; Chiarini, M.; Marinelli, F.; Rossi, L.; Arcadi, A. Adv. Synth. Catal. 2010, 352, 136.
Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.
doi: 10.1021/ar9502341
Ma, A. J.; Ready, J. M. Org. Lett. 2019, 21, 1148.
doi: 10.1021/acs.orglett.9b00098
Hosokawa, S.; Fumiyama, H.; Fukuda, H.; Fukuda, T.; Seki, M.; Tatsuta, K. Tetrahedron Lett. 2007, 48, 7305.
doi: 10.1016/j.tetlet.2007.08.037
Barros, M. T.; Maycock, C. D.; Ventura, M. R. Chem.-Eur. J. 2000, 6, 3991.
doi: 10.1002/1521-3765(20001103)6:21<3991::AID-CHEM3991>3.3.CO;2-M
Marion, N.; Ramon, R. S.; Nolan, S. P. J. Am. Chem. Soc. 2009, 131, 448.
doi: 10.1021/ja809403e
Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983.
doi: 10.1016/S0040-4039(00)78402-4
Tao Yang , Kaijiao Duan , Siyu Li , Jing Wei , Qingdi Yang , Qian Wang . A Comprehensive and Innovative Chemical Experimental Teaching: Extraction and Identification of Tea Polyphenols from Pu'er Tea and the Application in Hand Cream Making. University Chemistry, 2024, 39(8): 270-275. doi: 10.3866/PKU.DXHX202312040
Lijuan Wang , Yuping Ning , Jian Li , Sha Luo , Xiongfei Luo , Ruiwen Wang . Enhancing the Advanced Nature of Natural Product Chemistry Laboratory Courses with New Research Findings: A Case Study of the Application of Berberine Hydrochloride in Photodynamic Antimicrobial Films. University Chemistry, 2024, 39(11): 241-250. doi: 10.12461/PKU.DXHX202403017
Jiahui YU , Jixian DONG , Yutong ZHAO , Fuping ZHAO , Bo GE , Xipeng PU , Dafeng ZHANG . The morphology control and full-spectrum photodegradation tetracycline performance of microwave-hydrothermal synthesized BiVO4:Yb3+,Er3+ photocatalyst. Journal of Fuel Chemistry and Technology, 2025, 53(3): 348-359. doi: 10.1016/S1872-5813(24)60514-1
Xingchao Zhao , Xiaoming Li , Ming Liu , Zijin Zhao , Kaixuan Yang , Pengtian Liu , Haolan Zhang , Jintai Li , Xiaoling Ma , Qi Yao , Yanming Sun , Fujun Zhang . 倍增型全聚合物光电探测器及其在光电容积描记传感器上的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2311021-. doi: 10.3866/PKU.WHXB202311021
Hui Wang , Yiwen Zhang , Dong Liu . “三全育人”理念下培养应用型创新人才——以“赛教结合”模式为例的探索与实践. University Chemistry, 2025, 40(6): 37-42. doi: 10.12461/PKU.DXHX202407091
Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
Zihan Lin , Wanzhen Lin , Fa-Jie Chen . Electrochemical Modifications of Native Peptides. University Chemistry, 2025, 40(3): 318-327. doi: 10.12461/PKU.DXHX202406089
Liang TANG , Jingfei NI , Kang XIAO , Xiangmei LIU . Synthesis and X-ray imaging application of lanthanide-organic complex-based scintillators. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1892-1902. doi: 10.11862/CJIC.20240139
Li'na ZHONG , Jingling CHEN , Qinghua ZHAO . Synthesis of multi-responsive carbon quantum dots from green carbon sources for detection of iron ions and L-ascorbic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(4): 709-718. doi: 10.11862/CJIC.20240280
Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
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
Jianyu Qin , Yuejiao An , Yanfeng Zhang . In Situ Assembled ZnWO4/g-C3N4 S-Scheme Heterojunction with Nitrogen Defect for CO2 Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408002-. doi: 10.3866/PKU.WHXB202408002
Jinwang Wu , Qijing Xie , Chengliang Zhang , Haifeng Shi . 自旋极化增强ZnFe1.2Co0.8O4/BiVO4 S型异质结光催化性能降解四环素. Acta Physico-Chimica Sinica, 2025, 41(5): 100050-. doi: 10.1016/j.actphy.2025.100050
Zhonghong Yan , Chunxia Li , Ruolin Yang . Analysis of the Use and Effectiveness of Concept Mapping Assignments in English Medium Instruction of General Chemistry. University Chemistry, 2025, 40(4): 224-231. doi: 10.12461/PKU.DXHX202405138
Xue Dong , Xiaofu Sun , Shuaiqiang Jia , Shitao Han , Dawei Zhou , Ting Yao , Min Wang , Minghui Fang , Haihong Wu , Buxing Han . 碳修饰的铜催化剂实现安培级电流电化学还原CO2制C2+产物. Acta Physico-Chimica Sinica, 2025, 41(3): 2404012-. doi: 10.3866/PKU.WHXB202404012
Yang Xia , Kangyan Zhang , Heng Yang , Lijuan Shi , Qun Yi . 构建双通道路径增强iCOF/Bi2O3 S型异质结在纯水体系中光催化合成H2O2性能. Acta Physico-Chimica Sinica, 2024, 40(11): 2407012-. doi: 10.3866/PKU.WHXB202407012
Weikang Wang , Yadong Wu , Jianjun Zhang , Kai Meng , Jinhe Li , Lele Wang , Qinqin Liu . 三聚氰胺泡沫支撑的S型硫铟锌镉/硫掺杂氮化碳异质结的绿色H2O2合成:协同界面电荷转移调控与局域光热效应. Acta Physico-Chimica Sinica, 2025, 41(8): 100093-. doi: 10.1016/j.actphy.2025.100093
Min WANG , Dehua XIN , Yaning SHI , Wenyao ZHU , Yuanqun ZHANG , Wei ZHANG . Construction and full-spectrum catalytic performance of multilevel Ag/Bi/nitrogen vacancy g-C3N4/Ti3C2Tx Schottky junction. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1123-1134. doi: 10.11862/CJIC.20230477
Peihong Fan , Hongxiang Lou . 研究生高等天然药物化学课程的教学改革探索——导学互促式混合课堂教学与自主学习能力培养. University Chemistry, 2025, 40(6): 16-21. doi: 10.12461/PKU.DXHX202407078
Yuchen Zhou , Huanmin Liu , Hongxing Li , Xinyu Song , Yonghua Tang , Peng Zhou . Designing thermodynamically stable noble metal single-atom photocatalysts for highly efficient non-oxidative conversion of ethanol into high-purity hydrogen and value-added acetaldehyde. Acta Physico-Chimica Sinica, 2025, 41(6): 100067-. doi: 10.1016/j.actphy.2025.100067