Synthetic Progress of Polycyclic Xanthone

doi:10.6023/cjoc201911007

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (3): 551-562.DOI: 10.6023/cjoc201911007 Previous Articles Next Articles

多环型Xanthone类天然产物的合成研究进展

谢涛^a, 何海兵^b, 高栓虎^a,b

a 华东师范大学化学与分子工程学院上海绿色化学与化工工程绿色化重点实验室上海 200062;
b 华东师范大学上海分子治疗与新药创制工程技术研究中心上海 200062

收稿日期:2019-11-06 修回日期:2019-11-26 发布日期:2020-04-02
通讯作者: 何海兵, 高栓虎 E-mail:hbhe@chem.ecnu.edu.cn;shgao@chem.ecnu.edu.cn
基金资助:
国家自然科学基金（Nos.21971068，21772044）、上海市优秀学术/技术带头人计划（No.18XD1401500）、上海市科委基础研究项目（No.18JC1411303）、教育部创新团队和中央高校基本科研业务费专项资金资助项目.

Synthetic Progress of Polycyclic Xanthone

Xie Tao^a, He Haibing^b, Gao Shuanhu^a,b

a Shanghai Key Laboratory of Green Chemistry and Chemical Processes, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200062;
b Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, Shanghai 200062

Received:2019-11-06 Revised:2019-11-26 Published:2020-04-02
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21971068, 21772044), the Program of Shanghai Academic/Technology Research Leader (No. 18XD1401500), the Program of Shanghai Science and Technology Committee (No. 18JC1411303), the National Young Top-Notch Talent Support Program and the Fundamental Research Funds for the Central Universities.

Polycyclic xanthone natural products are a family of polyketides which are characterized by highly oxygenated angular hexacyclic frameworks. In the last decade, there has been a noticeable increase in reports on both synthetic and pharmacological investigations of this class of natural molecules due to their unique chemical structures and biological activities. Most members of this class of molecules show strong activities towards Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus, potent antifungal activity and antitumour activity. The synthetic studies of some members of this class of natural products is summarized.

Key words: polycyclic xanthone, natural product, total synthesis

Cite this article

Xie Tao, He Haibing, Gao Shuanhu. Synthetic Progress of Polycyclic Xanthone[J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 551-562.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Masters, K. S.; Brase, S. Chem. Rev. 2012, 112, 3717.
[2] (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.
[3] 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.
[4] Pinto, M. M.M.; Sousa, M. E.; Nascimento, M. S. Curr. Med. Chem. 2005, 12, 2517.
[5] Lesch, B.; Bräse, S. Angew. Chem., Int. Ed. 2004, 43, 115.
[6] Winter, D. K.; Sloman, D. L.; Porco, J. Nat. Prod. Rep. 2013, 30, 382.
[7] 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.
[8] (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.
[9] (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.
[10] 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.
[11] Kunimoto, S.; Someno, T.; Yamazaki, Y.; Lu, J.; Esumi, H.; Naganawa, H. J. Antibiot. 2003, 56, 1012.
[12] 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.
[13] Qiao, Y.-F.; Okazaki, T.; Ando, T.; Mizoue, K.; Kondo, K.; Eguchi, T.; Kakinuma, K. J. Antibiot. 1998, 51, 282.
[14] Kondo, K.; Eguchi, T.; Kakinuma, K.; Mizoue, K.; Qiao, Y.-F. J. Antibiot. 1998, 51, 288.
[15] Malet-Cascon, L.; Romero, F.; Espliego-Vazquez, F.; Gravalos, D.; Fernandez-Puentes, J. L. J. Antibiot. 2003, 56, 219.
[16] Rodriguez, J. C.; Puentes, J. L. F.; Baz, J. P.; Canedo, L. M. J. Antibiot. 2003, 56, 318.
[17] Omura, S.; Iwai, Y.; Hinotozawa, K.; Takahashi, Y.; Kato, J.; Nakagawa, A.; Hirano, A.; Shimizu, H.; Haneda, K. J. Antibiot. 1982, 35, 645.
[18] Omura, S.; Nakagawa, A.; Kushida, K.; Lukacs, G. J. Am. Chem. Soc. 1986, 108, 6088.
[19] 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.
[20] Carter, G. T.; Nietsche, J. A.; Williams, D. R.; Borders, D. B. J. Antibiot. 1990, 43, 504.
[21] Kelly, T. R.; Jagoe, C. T.; Li, Q. J. Am. Chem. Soc. 1989, 111, 4522.
[22] (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.
[23] Masuo, R.; Ohmori, K.; Hintermann, L.; Yoshida, S.; Suzuki, K. Angew. Chem., Int. Ed. 2009, 48, 3462.
[24] Sloman, D. L.; Bacon, J. W.; Porco, J. A. J. Am. Chem. Soc. 2011, 133, 9952.
[25] Butler, J. R.; Wang, C.; Bian, J.; Ready, J. M. J. Am. Chem. Soc. 2011, 133, 9956.
[26] Wang, Y.; Wang, C.; Butler, J. R.; Ready, J. M. Angew. Chem., Int. Ed. 2013, 52, 10796.
[27] Dai, Y.; Ma, F.; Shen, Y.; Xie, T.; Gao, S. Org. Lett. 2018, 20, 2872.
[28] (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.
[29] Tamiya, M.; Ohmori, K.; Kitamura, M.; Kato, H.; Arai, T.; Oorui, M.; Suzuki, K. Chem.-Eur. J. 2007, 13, 9791.
[30] (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.
[31] Ratnayake, R.; Lacey, E.; Tennant, S.; Gill, J. H.; Capon, R. J. Org. Lett. 2006, 8, 5267.
[32] Winter, D. K.; Endoma-Arias, M. A.; Hudlicky, T.; Beutler, J. A.; Porco, J. A. J. Org. Chem. 2013, 78, 7617.
[33] Sloman, D. L.; Mitasev, B.; Scully, S. S.; Beutler, J. A.; Porco, J. A. Angew. Chem., Int. Ed. 2011, 50, 2511.
[34] (a) Wei, H.-X.; Timmons, C.; Farag, M. A.; Pare, P. W.; Li, G. Org. Biomol. Chem. 2004, 2, 2893.
(b) Wei, H.-X.; Hu, J.; Jasoni, R. L.; Li, G.; Pare, P. W. Helv. Chim. Acta 2004, 87, 2359.
(c) Dai, Y.; Shen, Y.; Gao, S. Chin. J. Org. Chem. 2018, 38, 1608(in Chinese). (代义华, 申艳芳, 高栓虎, 有机化学, 2018, 38, 1608.)
[35] Endoma, M. A. A.; Bai, V. P.; Hansen, J.; Hudlicky, T. Org. Process Res. Dev. 2002, 6, 525.
[36] (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.
[37] Yang, J.; Knueppel, D.; Cheng, B.; Mans, D.; Martin, S. F. Org. Lett. 2015, 17, 114.
[38] Shi, Y. Acc. Chem. Res. 2004, 37, 488.
[39] Nicolaou, K. C.; Li, A. Angew. Chem., Int. Ed. 2008, 47, 6579.
[40] (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.
[41] Castillo-Contreras, E. B.; Dake, G. R. Org. Lett. 2014, 16, 1642.
[42] (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.
[43] Noyori, R.; Hashiguchi, S. Acc. Chem. Res. 1997, 30, 97.
[44] Ma, A. J.; Ready, J. M. Org. Lett. 2019, 21, 1148.
[45] Hosokawa, S.; Fumiyama, H.; Fukuda, H.; Fukuda, T.; Seki, M.; Tatsuta, K. Tetrahedron Lett. 2007, 48, 7305.
[46] Barros, M. T.; Maycock, C. D.; Ventura, M. R. Chem.-Eur. J. 2000, 6, 3991.
[47] Marion, N.; Ramon, R. S.; Nolan, S. P. J. Am. Chem. Soc. 2009, 131, 448.
[48] Noji, M.; Nakajima, M.; Koga, K. Tetrahedron Lett. 1994, 35, 7983.

多环型Xanthone类天然产物的合成研究进展

Synthetic Progress of Polycyclic Xanthone

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Weizhong Ding, Bingwen Zhang, Yanqing Xue, Yuqi Lin, Zhijun Tang, Jing Wang, Wenchao Yang, Xiaofeng Wang, Wen Liu. A New Polyketide from Fusarium graminearum [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3319-3322.
[2]	Xiurong Wu, Chaojiang Xiao, Yi Shen, Hongxia Tang, Junyi Zhu, Bei Jiang. Research Progress on Antimalarial Natural Sesquiterpenoids from Plants from 1972 to 2022 [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2764-2789.
[3]	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.
[4]	Huaiyuan Zhang, Nuo Xu, Rongping Tang, Xingli Shi. Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3784-3805.
[5]	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.
[6]	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.
[7]	Liangcai Yao, Jinghan Gui. Application of the Radical Polyene Cyclization Reaction in Natural Product Synthesis [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2703-2714.
[8]	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.
[9]	Fasheng Shi, Shengwen Wang, Huan Xu, Xingxing Lu, Xinling Yang, Tengda Sun, Changkai Wang, Xiaoming Zhang, Qing Yang, Yun Ling. Design, Synthesis and Fungicidal Actiνity of Noνel Thiosemicarbazide Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2106-2116.
[10]	Yaqian Yan, Haoxin Wang, Yaoyao Li. Discovery of a New Polycyclic Tetramate Macrolactam 3-Hydroxycombamide I [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1557-1561.
[11]	Jie Luo, Yaqian Yan, Haoxin Wang, Yaoyao Li. Discovery of a New Polycyclic Tetramate Macrolactam Clifednamide K [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1224-1228.
[12]	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.
[13]	Wei Chen, Qiang Liu. Recent Advances in the Oxidative Coupling Reaction of Enol Derivatives [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3414-3430.
[14]	Quancheng Li, Lan Jiang, Rui Bai, Yongkang Han, Zhengning Li. Progress in the Synthesis of 3-Substituted Phthaides [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3390-3399.
[15]	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.