Recent Advance in the Synthesis of Natural Products of Schisandra Triterpenoid

doi:10.6023/cjoc202105049

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (10): 3816-3825.DOI: 10.6023/cjoc202105049 Previous Articles Next Articles

Special Issue: 南开大学化学学科创立100周年

REVIEWS

五味子三萜天然产物的合成进展

郭璐, 汤平平^*()

南开大学化学学院元素有机化学国家重点实验室天津 300071

收稿日期:2021-05-28 修回日期:2021-07-15 发布日期:2021-08-17
通讯作者: 汤平平
基金资助:
国家重点研发计划(2016YFA0602900); 国家自然科学基金(21672110); 国家自然科学基金(21925105); 天津市自然科学基金(18JCJQJC47000)

Recent Advance in the Synthesis of Natural Products of Schisandra Triterpenoid

Lu Guo, Pingping Tang()

State Key Laboratory of Elemento-organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071

Received:2021-05-28 Revised:2021-07-15 Published:2021-08-17
Contact: Pingping Tang
Supported by:
National Key Research and Development Program of China(2016YFA0602900); National Natural Science Foundation of China(21672110); National Natural Science Foundation of China(21925105); Natural Science Foundation of Tianjin City(18JCJQJC47000)

Cite this article

Lu Guo, Pingping Tang. Recent Advance in the Synthesis of Natural Products of Schisandra Triterpenoid[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3816-3825.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 7

Scheme 1. Basic structure of Schisandra triterpenoid natural products

Scheme 2. Segments of synthesis about schisandra triterpenoid natural products

Scheme 3. Total synthesis of Schisandra triterpenoid natural products

Scheme 4. Ding's total synthesis of atrop-schiglautone A

Scheme 5. Anderson's total synthsis of (–)-rubriflordilactone B

Scheme 6. Yang's total synthesis of pre-schisanartanin C

Scheme 7. Gui's total synthesis of propindilactone G

References 56

[1]	Xiao, W. L.; Li, R. T.; Huang, S. X.; Pu, J. X.; Sun, H. D. Nat. Prod. Rep. 2008, 25, 871. doi: 10.1039/b719905h
[2]	Shi, Y. M.; Xiao, W. L.; Pu, J. X.; Sun, H. D. Nat. Prod. Rep. 2015, 32, 367. doi: 10.1039/C4NP00117F
[3]	Tang, Y.; Zhang, Y.; Dai, M.; Luo, T.; Deng, L.; Chen, J.; Yang, Z. Org. Lett. 2005, 7, 885. doi: 10.1021/ol047394+
[4]	Hui, Y. Z. Comprehensive Natural Products in Tradational Chinese Medicine, Shanghai Scientific and Technical Publishers, Shanghai, 2011. (in Chinese)
	(惠永正, 中药天然产物大全, 上海科学技术出版社, 上海, 2011.)
[5]	Li, R. T.; Zhao, Q. S.; Li, S. H.; Han, Q. Bin; Sun, H. D.; Lu, Y.; Zhang, L. L.; Zheng, Q. T. Org. Lett. 2003, 5, 1023. doi: 10.1021/ol027524j
[6]	Zhang, Y. D.; Tang, Y. F.; Luo, T. P.; Shen, J.; Chen, J. H.; Yang, Z. Org. Lett. 2006, 8, 107. pmid: 16381579
[7]	Zhang, Y. D.; Ren, W. W.; Lan, Y.; Xiao, Q.; Wang, K.; Xu, J.; Chen, J. H.; Yang, Z. Org. Lett. 2008, 10, 665. doi: 10.1021/ol703126q pmid: 18215052
[8]	Krishnan, K. S.; Smitha, M.; Suresh, E.; Radhakrishnan, K. V. Tetrahedron 2006, 62, 12345. doi: 10.1016/j.tet.2006.09.102
[9]	Fischer, D.; Theodorakis, E. A. Eur. J. Org. Chem. 2007, 25, 4193.
[10]	Wang, Q.; Chen, C. Org. Lett. 2008, 10, 1223. doi: 10.1021/ol800111j
[11]	Paquette, L. A.; Kwong, W. L. Org. Lett. 2008, 10, 2111. doi: 10.1021/ol800418m pmid: 18454534
[12]	Kwong, W. L.; Paquette, L. A. Org. Lett. 2008, 10, 2115. doi: 10.1021/ol800419v pmid: 18454538
[13]	Paquette, L. A.; Lai, K. W. Org. Lett. 2008, 10, 3781. doi: 10.1021/ol8014607 pmid: 18683932
[14]	Cordonnier, M. C. A.; Jennifer Kan, S. B.; Anderson, E. A. Chem. Commun. 2008, 44, 5818.
[15]	Goh, S. S.; Baars, H.; Gockel, B.; Anderson, E. A. Org. Lett. 2012, 14, 6278. doi: 10.1021/ol303041j
[16]	Gockel, B.; Goh, S. S.; Puttock, E. J.; Baars, H.; Chaubet, G.; Anderson, E. A. Org. Lett. 2014, 16, 4480. doi: 10.1021/ol502027m
[17]	Mehta, G.; Bhat, A. B.; Kumara, T. H. S. Tetrahedron Lett. 2009, 50, 6597. doi: 10.1016/j.tetlet.2009.09.059
[18]	Mehta, G.; Bhat, B. A.; Suresha Kumara, T. H. Tetrahedron Lett. 2010, 51, 4069. doi: 10.1016/j.tetlet.2010.05.130
[19]	Mehta, G.; Bhat, B. A. Tetrahedron Lett. 2009, 50, 2474. doi: 10.1016/j.tetlet.2009.03.040
[20]	Mehta, G.; Yaragorla, S. A. Tetrahedron Lett. 2013, 54, 549. doi: 10.1016/j.tetlet.2012.11.080
[21]	Matcha, K.; Maity, S.; Malik, C. K.; Ghosh, S. Tetrahedron Lett. 2010, 51, 2754. doi: 10.1016/j.tetlet.2010.03.074
[22]	Maity, S.; Matcha, K.; Ghosh, S. J. Org. Chem. 2010, 75, 4192. doi: 10.1021/jo1006448
[23]	Hossain, M. F.; Matcha, K.; Ghosh, S. Tetrahedron Lett. 2011, 52, 6473. doi: 10.1016/j.tetlet.2011.09.104
[24]	Bartoli, A.; Chouraqui, G.; Parrain, J. L. Org. Lett. 2012, 14, 122. doi: 10.1021/ol2029146
[25]	Peng, Y.; Duan, S. M.; Wang, Y. W. Tetrahedron Lett. 2015, 56, 4509. doi: 10.1016/j.tetlet.2015.05.117
[26]	Wang, Y.; Li, Z.; Lv, L.; Xie, Z. Org. Lett. 2016, 18, 792. doi: 10.1021/acs.orglett.6b00057
[27]	Wang, Y.; Zhang, Y.; Li, Z.; Yang, Z.; Xie, Z. Org. Chem. Front. 2017, 4, 47. doi: 10.1039/C6QO00241B
[28]	Werner, B.; Kalesse, M. Org. Lett. 2017, 19, 1524. doi: 10.1021/acs.orglett.7b00288
[29]	Sun, T. W.; Ren, W. W.; Xiao, Q.; Tang, Y. F.; Zhang, Y. D.; Li, Y.; Meng, F. K.; Liu, Y. F.; Zhao, M. Z.; Xu, L. M.; Chen, J. H.; Yang, Z. Chem. Asian J. 2012, 7, 2321. doi: 10.1002/asia.201200363
[30]	Li, Y.; Chen, Z. X.; Xiao, Q.; Ye, Q. D.; Sun, T. W.; Meng, F. K.; Ren, W. W.; You, L.; Xu, L. M.; Wang, Y. F.; Chen, J. H.; Yang, Z. Chem. Asian J. 2012, 7, 2334. doi: 10.1002/asia.201200364
[31]	Ren, W. W.; Chen, Z. X.; Xiao, Q.; Li, Y.; Sun, T. W.; Zhang, Z. Y.; Ye, Q. D.; Meng, F. K.; You, L.; Zhao, M. Z.; Xu, L. M.; Tang, Y. F.; Chen, J. H.; Yang, Z. Chem. Asian J. 2012, 7, 2341. doi: 10.1002/asia.201200365
[32]	Xiao, Q.; Ren, W. W.; Chen, Z. X.; Sun, T. W.; Li, Y.; Ye, Q. D.; Gong, J. X.; Meng, F. K.; You, L.; Liu, Y. F.; Zhao, M. Z.; Xu, L. M.; Shan, Z. H.; Shi, Y.; Tang, Y. F.; Chen, J. H.; Yang, Z. Angew. Chem., nt. Ed. 2011, 50, 7373.
[33]	You, L.; Liang, X. T.; Xu, L. M.; Wang, Y. F.; Zhang, J. J.; Su, Q.; Li, Y. H.; Zhang, B.; Yang, S. L.; Chen, J. H.; Yang, Z. J. Am. Chem. Soc. 2015, 137, 10120. doi: 10.1021/jacs.5b06480
[34]	Han, Y. X.; Jiang, Y. L.; Li, Y.; Yu, H. X.; Tong, B. Q.; Niu, Z.; Zhou, S. J.; Liu, S.; Lan, Y.; Chen, J. H.; Yang, Z. Nat. Commun. 2017, 8, 1. doi: 10.1038/ncomms15797
[35]	Liu, D. D.; Sun, T. W.; Wang, K. Y.; Lu, Y.; Zhang, S. L.; Li, Y. H.; Jiang, Y. L.; Chen, J. H.; Yang, Z. J. Am. Chem. Soc. 2017, 139, 5732. doi: 10.1021/jacs.7b02561
[36]	Jiang, Y. L.; Yu, H. X.; Li, Y.; Qu, P.; Han, Y. X.; Chen, J. H.; Yang, Z. J. Am. Chem. Soc. 2020, 142, 573. doi: 10.1021/jacs.9b11872 pmid: 31789517
[37]	Wang, Y.; Chen, B.; He, X.; Gui, J. J. Am. Chem. Soc. 2020, 142, 5007. doi: 10.1021/jacs.0c00363 pmid: 32119544
[38]	Wang, Y.; Chen, B.; He, X.; Gui, J. Chin. J. Chem. 2020, 38, 1339. doi: 10.1002/cjoc.v38.11
[39]	Li, J.; Yang, P.; Yao, M.; Deng, J.; Li, A. J. Am. Chem. Soc. 2014, 20, 8.
[40]	Yang, P.; Yao, M.; Li, J.; Li, Y.; Li, A. Angew. Chem., nt. Ed. 2016, 55, 6964.
[41]	Goh, S. S.; Chaubet, G.; Gockel, B.; Cordonnier, M.-C. A.; Baars, H.; Phillips, A. W.; Anderson, E. A. Angew. Chem., Int. Ed. 2015, 54, 12618. doi: 10.1002/anie.201506366
[42]	Mohammad, M.; Chintalapudi, V.; Carney, J. M.; Mansfield, S. J.; Sanderson, P.; Christensen, K. E.; Anderson, E. A. Angew. Chem., nt. Ed. 2019, 58, 18177.
[43]	Ma, B.; Zhao, Y.; He, C.; Ding, H. Angew. Chem., nt. Ed. 2018, 57, 15567.
[44]	Wang, H.; Zhang, X.; Tang, P. Chem. Sci. 2017, 8, 7246. doi: 10.1039/C7SC03293E
[45]	Wang, H.; Wang, L.; Li, Y.; Zhang, X.; Tang, P. Chin. J. Chem. 2019, 37, 255.
[46]	Wang, L.; Wang, H.; Li, Y.; Tang, P. Angew. Chem., nt. Ed. 2015, 54, 5732.
[47]	Li, X.; Cheong, P. H. Y.; Carter, R. G. Angew. Chem., nt. Ed. 2017, 56, 1704.
[48]	Yan, B.; Hu, K.; Sun, H.; Puno, P. Chin. J. Org. Chem. 2018, 38, 2259. (in Chinese) doi: 10.6023/cjoc201806002
	(颜秉超, 胡坤, 孙汉董, 普诺•白玛丹增, 有机化学, 2018, 38, 2259.)
[49]	Yang, Z. Acc. Chem. Res. 2019, 52, 480. doi: 10.1021/acs.accounts.8b00569
[50]	Bhat, B. A.; Rashid, S.; Sengupta, S.; Mehta, G. Asian J. Org. Chem. 2020, 9, 449. doi: 10.1002/ajoc.v9.4
[51]	Fu, S.; Liu, B. Org. Chem. Front. 2020, 7, 1903. doi: 10.1039/D0QO00203H
[52]	Meng, F. Y.; Sun, J. X.; Li, X.; Yu, H. Y.; Li, S. M.; Ruan, H. L. Org. Lett. 2011, 13, 1502. doi: 10.1021/ol200188n
[53]	Xiao, W. L.; Yang, L. M.; Gong, N. B.; Wu, L.; Wang, R. R.; Pu, J. X.; Li, X. L.; Huang, S. X.; Zheng, Y. T.; Li, R. T.; Lu, Y.; Zheng, Q. T.; Sun, H. D. Org. Lett. 2006, 8, 991. doi: 10.1021/ol060062f
[54]	Yang, P.; Li, J.; Sun, L.; Yao, M.; Zhang, X.; Xiao, W. L.; Wang, J. H.; Tian, P.; Sun, H. D.; Puno, P. T.; Li, A. J. Am. Chem. Soc. 2020, 142, 13701. doi: 10.1021/jacs.9b09699
[55]	Lei, C.; Xiao, W. L.; Huang, S. X.; Chen, J. J.; Pu, J. X.; Sun, H. D. Tetrahedron 2010, 66, 2306. doi: 10.1016/j.tet.2010.02.002
[56]	Lei, C.; Huang, S. X.; Chen, J. J.; Yang, L. Bin; Xiao, W. L.; Chang, Y.; Lu, Y.; Huang, H.; Pu, J. X.; Sun, H. D. J. Nat. Prod. 2008, 71, 1228. doi: 10.1021/np8001699

五味子三萜天然产物的合成进展

Recent Advance in the Synthesis of Natural Products of Schisandra Triterpenoid

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 7

References 56

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	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.
[2]	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.
[3]	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.
[4]	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.
[5]	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.
[6]	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.
[7]	Minxin Li, Qiuping Zou, Wenrong Du, Jinchun Gao, Yanping Li, Zewei Mao. Total Synthesis and Anti-inflammatory Evaluation of Dorsmerunin A [J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 3292-3296.
[8]	Jian Xiao, Yu Peng, Wei-Dong Z. Li. Advances on the Total Synthesis of Sesquiterpenoid Alkaloid Dendrobine [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2636-2649.
[9]	Xifei Yan, Jianfeng Zheng, Wei-Dong Z. Li. Studies on the Chemical Synthesis of Natural Drugs Berberine [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2217-2227.
[10]	Gang Yang, Xiangyu Feng, Congcong Han, Yang Chen, Shuzhong He. Synthesis of the ABC Ring System of Wallichanol Natural Product [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 726-730.
[11]	Ding Ma, Junli Ao, Naifeng Hu, Guangxin Liang. Progress in Biological Activity and Synthesis of Nematode Hatching Pheromone Glycinoeclepin A [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 553-566.
[12]	Han Jilai, Tang Meilin, Sun Xun. Study on the Total Synthesis of Resveratrol Dimers Quadrangularin A and Pallidol [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1571-1577.
[13]	Dong Wei, Wang Xin, Ge Zemei, He Fang, Li Runtao. Efficient Synthesis of Wogonin [J]. Chinese Journal of Organic Chemistry, 2020, 40(6): 1725-1730.
[14]	Xie Tao, He Haibing, Gao Shuanhu. Synthetic Progress of Polycyclic Xanthone [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 551-562.
[15]	Sun Zezhong, Xu Miao, Wang Yunxia, Hu Xiangdong. Synthetic Progress of Alkaloids against Mycobacterium Tuberculosis: Pseudopteroxazole and Ileabethoxazole [J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4203-4215.