Advances in the Collective Synthesis of Lycopodium Alkaloids

doi:10.6023/cjoc201611032

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (4): 810-823.DOI: 10.6023/cjoc201611032 Previous Articles Next Articles

REVIEW

石松生物碱集成合成的研究进展

肖春霞^a, 曹林^a, 王佳^a, 苗银龙^a, 范华芳^a,b

a. 西北农林科技大学陕西省天然产物化学生物学重点实验室杨凌 712100;
b. 中国科学院上海有机化学研究所中国科学院天然产物有机合成化学重点实验室上海 200032

收稿日期:2016-11-24 修回日期:2016-12-24 发布日期:2017-01-17
通讯作者: 范华芳 E-mail:fhf@nwafu.edu.cn
基金资助:
国家自然科学基金（Nos.21403169，21502153）、中国博士后科学基金（No.2013M532084）、中央高校基本科研业务费（No.2452015079）资助项目.

Advances in the Collective Synthesis of Lycopodium Alkaloids

Xiao Chunxia^a, Cao Lin^a, Wang Jia^a, Miao Yinlong^a, Fan Huafang^a,b

a. Shaanxi Key Laboratory of Natural Products & Chemical Biology, Northwest A&F University, Yangling 712100;
b. Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2016-11-24 Revised:2016-12-24 Published:2017-01-17
Contact: 10.6023/cjoc201611032 E-mail:fhf@nwafu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21403169, 21502153), the Postdoctoral Science Foundation of China (No. 2013M532084) and the Chinese Universities Scientific Fund (No. 2452015079).

In view of the relevance between chemical structures and biosynthetic pathways of compounds that belong to the same family of natural products, MacMillan et al. (2011) proposed a strategy for the rapid and efficient synthesis of natural product within a family from a common intermediate or a group of similar intermediates, which is termed as collective synthesis. In recent years, this strategy has been applied for the synthesis of multiple family of natural products. Lycopodium alkaloids are a class of structurally diverse alkaloids, and many of them exhibiting good biological activity. In this review, the progress in the collective synthesis of Lycopodium alkaloids is summarized.

Key words: Lycopodium alkaloids, natural products, total synthesis, collective synthesis

Cite this article

Xiao Chunxia, Cao Lin, Wang Jia, Miao Yinlong, Fan Huafang. Advances in the Collective Synthesis of Lycopodium Alkaloids[J]. Chin. J. Org. Chem., 2017, 37(4): 810-823.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] (a) Zhao, G.; Dai, S.; Chen, R. Dictionary of Traditional Chinese Medicine, 2 ed., Shanghai Scienfitic & Technical Publishers, Shanghai, 2009, pp. 284~285, 774~775, 1590~1591 (in Chinese).
(赵国平, 戴慎, 陈仁寿, 中药大辞典, 第二版, 上海科学技术出版社, 上海, 2009, pp. 284~285, 774~775, 1590~1591.)
[2] Choo, C. Y.; Hirasawa, Y.; Karimata, C.; Koyama, K.; Sekiguchi, M.; Kobayashi, J. I.; Morita, H. Bioorg. Med. Chem. 2007, 15, 1703.
[3] (a) Mandal, S. K.; Biswas, R.; Bhattacharyya, S. S.; Paul, S.; Dutta, S.; Pathak, S.; Khuda-Bukhsh, A. R. Eur. J. Pharmacol. 2010, 626, 115.
(b) Ham, Y.-M.; Yoon, W.-J.; Park, S.-Y.; Jung, Y.-H.; Kim, D.; Jeon, Y.-J.; Wijesinghe, W.; Kang, S.-M.; Kim, K.-N. Food Chem. Toxicol. 2012, 50, 2629.
[4] He, J.; Chen, X.-Q.; Li, M.-M.; Zhao, Y.; Xu, G.; Cheng, X.; Peng, L.-Y.; Xie, M.-J.; Zheng, Y.-T.; Wang, Y.-P. Org. Lett. 2009, 11, 1397.
[5] Yuan, C.; Chang, C. -T.; Axelrod, A.; Siegel, D. J. Am. Chem. Soc. 2010, 132, 5924.
[6] Feng, X.; Jiang, H.; Zhang, Y.; He, W.; Zhang, L. J. Med. Plants Res. 2012, 6, 1263.
[7] (a) Ayer, W. A. Nat. Prod. Rep. 1991, 8, 455.
(b) Maclean, D. B. In The Alkaloids: Chemistry and Pharmacology, Vol. 26, Ed.: Arnold, B., Academic Press, New York, 1985, Chapter 5.
(c) Luan, X.; Xu, Z. Acta Pharm. Sin. 1986, 21, 310 (in Chinese).
(栾新慧, 徐择邻, 药学学报, 1986, 21, 310.)
(d) Yuan, S.; Luan, X. Bull. Acad. Mil. Med. Sci. 1999, 23, 58 (in Chinese).
(袁珊琴, 栾新慧, 军事医学科学院院刊, 1999, 23, 58.)
(e) Tan, C.; Zhu, D. Chin. J. Nat. Med. 2003, 1, 1 (in Chinese).
(谭昌恒; 朱大元, 中国天然药物, 2003, 1, 1.)
(f) Chen, Y.; Liu, Y.; Jiang, J.; Liu, B. J. Yunnan Normal Univ. (Nat. Sci. Ed.) 2010, 30, 12 (in Chinese).
(陈业高; 刘怡君; 蒋金和; 刘波, 云南师范大学学报(自然科学版), 2010, 30, 12.)
[8] Liu, J.; Yu, C.; Zhou, Y.; Han, Y.; Qi, B.; Zhu, Y. Acta Chim. Sinica 1986, 44, 1035 (in Chinese).
(刘嘉森; 俞超美; 周有作, 化学学报, 1986, 44, 1035.)
[9] (a) Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2012, 75, 311.
(b) Li, J. W. -H.; Vederas, J. C. Science 2009, 325, 161.
[10] (a) Jones, S. B.; Simmons, B.; Mastracchio, A.; MacMillan, D. W. C. Nature 2011, 475, 183.
(b) Schreiber, S. L. Science 2000, 287, 1964.
[11] (a) Yang, H.; Carter, R. G.; Zakharov, L. N. J. Am. Chem. Soc. 2008, 130, 9238.
(b) Yang, H.; Carter, R. G. J. Org. Chem. 2010, 75, 4929.
[12] (a) Saha, M.; Carter, R. G. Org. Lett. 2013, 15, 736.
(b) Saha, M.; Li, X.; Collett, N. D.; Carter, R. G. J. Org. Chem. 2016, 81, 5963.
[13] Ding, R.; Sun, B.-F.; Lin, G.-Q. Org. Lett. 2012, 14, 4446.
[14] (a) Ding, R.; Fu, J.-G.; Xu, G.-Q.; Sun, B.-F.; Lin, G.-Q. J. Org. Chem. 2014, 79, 240.
(b) Fu, J.-G.; Xu, G.-Q.; Ding, R.; Lin, G.-Q.; Sun, B.-F. Org. Chem. Front. 2016, 3, 62.
[15] (a) Heathcock, C. H.; Smith, K. M.; Blumenkopf, T. A. J. Am. Chem. Soc. 1986, 108, 5022.
(b) Heathcock, C. H.; Blumenkopf, T. A.; Smith, K. M. J. Org. Chem. 1989, 54, 1548.
[16] Murphy, R. A.; Sarpong, R. Chem.-Eur. J. 2014, 20, 42.
[17] Nakayama, A.; Kitajima, M.; Takayama, H. Synlett 2012, 23, 2014.
[18] (a) Otsuka, Y.; Inagaki, F.; Mukai, C. J. Org. Chem. 2010, 75, 3420.
(b) Kozaka, T.; Miyakoshi, N.; Mukai, C. J. Org. Chem. 2007, 72, 10147.
(c) Itoh, N.; Iwata, T.; Sugihara, H.; Inagaki, F.; Mukai, C. Chem.-Eur. J. 2013, 19, 8665.
[19] Pan, G.; Williams, R. M. J. Org. Chem. 2012, 77, 4801.
[20] (a) Zaimoku, H.; Taniguchi, T. Chem.-Eur. J. 2014, 20, 9613.
(b) Zaimoku, H.; Nishide, H.; Nishibata, A.; Goto, N.; Taniguchi, T.; Ishibashi, H. Org. Lett. 2013, 15, 2140.
[21] (a) Yang, Y.-R.; Lai, Z.-W.; Shen, L.; Huang, J.-Z.; Wu, X.-D.; Yin, J.-L.; Wei, K. Org. Lett. 2010, 12, 3430.
(b) Yang, Y.-R.; Shen, L.; Wei, K.; Zhao, Q.-S. J. Org. Chem. 2010, 75, 1317.
(c) Yang, Y.-R.; Shen, L.; Huang, J.-Z.; Xu, T.; Wei, K. J. Org. Chem. 2011, 76, 3684.
(d) Dong, L.-B.; Wu, Y.-N.; Jiang, S.-Z.; Wu, X.-D.; He, J.; Yang, Y.-R.; Zhao, Q.-S. Org. Lett. 2014, 16, 2700.
[22] Xu, T.; Luo, X.-L.; Yang, Y.-R. Tetrahedron Lett. 2013, 54, 2858.
[23] Jiang, S.-Z.; Lei, T.; Wei, K.; Yang, Y.-R. Org. Lett. 2014, 16, 5612.
[24] (a) Zhang, X.-M.; Tu, Y.-Q.; Zhang, F.-M.; Shao, H.; Meng, X. Angew. Chem., Int. Ed. 2011, 50, 3916.
(b) Zhang, X.-M.; Shao, H.; Tu, Y.-Q.; Zhang, F.-M.; Wang, S.-H. J. Org. Chem. 2012, 77, 8174.
[25] (a) Li, H.; Wang, X.; Lei, X. Angew Chem., Int. Ed. 2012, 51, 491.
(b) Li, H.; Wang, X.; Hong, B.; Lei, X. J. Org. Chem. 2013, 78, 800.
(c) Wang, X.; Li, H.; Lei, X. Synlett 2013, 24, 1032.
(d) Zhang, J.; Wu, J.; Hong, B.; Ai, W.; Wang, X.; Li, H.; Lei, X. Nat. Commun. 2014, 5, 4614.
(e) Hong, B.; Li, H.; Wu, J.; Zhang, J.; Lei, X. Angew. Chem., Int. Edit. 2015, 54, 1011.
[26] (a) Zeng, C.; Zheng, C.; Zhao, J.; Zhao, G. Org. Lett. 2013, 15, 5846.
(b) Zeng, C.; Zhao, J.; Zhao, G. Tetrahedron 2015, 71, 64.
[27] Hou, S.-H.; Tu, Y.-Q.; Liu, L.; Zhang, F.-M.; Wang, S.-H.; Zhang, X.-M. Angew. Chem., Int. Ed. 2013, 52, 11373.
[28] Wolfe, B. H.; Libby, A. H.; Al-Awar, R. S.; Foti, C. J.; Comins, D. L. J. Org. Chem. 2010, 75, 8564.
[29] Shigeyama, T.; Katakawa, K.; Kogure, N.; Kitajima, M.; Takayama, H. Org. Lett. 2007, 9, 4069.
[30] Tanaka, T.; Kogure, N.; Kitajima, M.; Takayama, H. J. Org. Chem. 2009, 74, 8675.
[31] (a) Bradshaw, B.; Luque-Corredera, C.; Bonjoch, J. Org. Lett. 2013, 15, 326.
(b) Bradshaw, B.; Luque-Corredera, C.; Bonjoch, J. Chem. Commun. 2014, 50, 7099.
(c) Bosch, C.; Bradshaw, B.; Bonjoch, J.; Fiser, B.; Gomez-Bengoa, E. Org. Lett. 2015, 17, 5084.
[32] Nishikawa, Y.; Kitajima, M.; Kogure, N.; Takayama, H. Tetrahedron 2009, 65, 1608.
[33] Liau, B. B.; Shair, M. D. J. Am. Chem. Soc. 2010, 132, 9594.
[34] Lee, A. S.; Liau, B. B.; Shair, M. D. J. Am. Chem. Soc. 2014, 136, 13442.

石松生物碱集成合成的研究进展

Advances in the Collective Synthesis of Lycopodium Alkaloids

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	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.
[2]	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.
[3]	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.
[4]	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.
[5]	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.
[6]	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.
[7]	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.
[8]	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.
[9]	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.
[10]	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.
[11]	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.
[12]	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.
[13]	Haixia Shi, Yaoyao Li, Jing Zhu, Haoxin Wang, Yuemao Shen. Discovery of Germicidin Glucuronides from Streptomyces sp. LZ35 [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2502-2506.
[14]	Ting Jiang, Hong Pu, Yanwen Duan, Xiaohui Yan, Yong Huang. New Natural Products of Streptomyces Sourced from Deep-Sea, Desert, Volcanic, and Polar Regions from 2009 to 2020 [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 1804-1820.
[15]	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.