Citation: Hao Erjun, Zhang Qing, Zhang Qiying, Qu Guirong, Yang Xining, Guo Haiming. Efficient Synthesis of Spirocyclic Nucleosides via Michael Addition-Initiated Intermolecular Cyclopropanation Reaction[J]. Chinese Journal of Organic Chemistry, ;2019, 39(11): 3237-3243. doi: 10.6023/cjoc201904074 shu

Efficient Synthesis of Spirocyclic Nucleosides via Michael Addition-Initiated Intermolecular Cyclopropanation Reaction

Hao Erjun ^a ,
Zhang Qing ^a ,
Zhang Qiying ^a,, ,
Qu Guirong ^a ,
Yang Xining ^b ,
Guo Haiming ^a,,

a.
Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007
b.
Xinxiang Tuoxin Pharmaceutical Co., Ltd., Xinxiang, Henan 453000

Corresponding author: Zhang Qiying, zhangqiying@htu.edu.cn Guo Haiming, ghm@htu.edu.cn
Received Date: 30 April 2019
Revised Date: 7 June 2019
Available Online: 24 November 2019
Fund Project: the Henan Postdoctoral Science Foundation Funded Project 2015071Overseas Expertise Introduction Project for Discipline Innovation D17007Project supported by the National Natural Science Foundation of China (Nos. 21602045, U1604283), the Henan Postdoctoral Science Foundation Funded Project (No. 2015071) and Overseas Expertise Introduction Project for Discipline Innovation (111 Project, No. D17007)the National Natural Science Foundation of China 21602045Overseas Expertise Introduction Project for Discipline Innovation 111计划the National Natural Science Foundation of China U1604283

Figures(3)

An efficient route to synthesize 2'-spiro[2-oxocyclopentyl]cyclopropyl nucleoside analogues via KO^tBu promoted Michael addition-initiated cyclopropanation reactions of α-thymine acrylates with α-chloro-cycloalkanones has been developed. A wide range of C(2')-spirocyclic modified nucleoside analogues were obtained with excellent diastereoselectivities (>20:1) and good yields (up to 85%).
- spirocyclic nucleoside,
- cyclopropanation reaction,
- α-chloro-cycloalkanone
1. [1]
2. [2]
  (a) Prota, A.; Vogt, J.; Pilger, B.; Perozzo, R.; Wurth, C.; Marquez, V. E.; Russ, P.; Schulz, G. E.; Folkers, G.; Scapozza, L. Biochemistry 2000, 39, 9597.
  (b) Jacobson, K. A.; Ji, X.; Li, A.; Melman, N.; Siddiqui, M. A.; Shin, K. J.; Marquez, V. E.; Ravi, R. G. J. Med. Chem. 2000, 43, 2196.
  (c) Nandanan, E.; Jang, S.-Y.; Moro, S.; Kim, H. O.; Siddiqui, M. A.; Russ, P.; Marquez, V. E.; Busson, R.; Herdewijn, P.; Harden, T. K.; Boyer, J. L.; Jacobson, K. A. J. Med. Chem. 2000, 43, 829.
3. [3]
  (a) Lemaire, S.; Diène, C.; Gavryushin, A.; Jourdin, X. M. D.; Paolini, L.; Jusseau, X.; Knochel, P.; Farina, V. J. Org. Chem. 2019, 84, 4910.
  (b) Kumar, R.; Kumar, M.; Singh, A.; Singh, N.; Maity, J.; Prasad, A. K. Carbohydr. Res. 2017, 445, 88.
  (c) Cobb, A. J. A.; Del'Isola, A.; Abdulsattar, B. O.; McLachlan, M. M. W.; Neuman, B. W.; Müller, C.; Shankland, K.; Al-Mulla, H. M. N.; Binks, A. W. D.; Elvidgeb, W. New J. Chem. 2018, 42, 18363.
  (d) Lebreton, J.; Escudier, J.-M.; Arzel, L.; Len, C. Chem. Rev. 2010, 110, 3371.
4. [4]
  Li, H.; Yoo, J. C.; Hong, J. H. Bull. Korean Chem. Soc. 2011, 32, 1146. doi: 10.5012/bkcs.2011.32.4.1146
5. [5]
  Zeng, D.; Zhang, R.; Nie, Q.; Cao, L.; Shang, L.; Yin, Z. ACS Med. Chem. Lett. 2016, 7, 1197. doi: 10.1021/acsmedchemlett.6b00270
6. [6]
  Jonckers, T. H. M.; Lin, T.; Buyck, C.; Lachau-Durand S.; Vandyck, K.; Hoof, S. V.; Vandekerckhove, L. A. M.; Hu, L.; Berke, J. M.; Vijgen, L.; Dillen, L. L. A.; Cummings, M. D.; de Kock, H.; Nilsson, M.; Sund, C.; Rydegård, C.; Samuelsson, B.; Rosenquist, Å.; Fanning, G.; Emelen, K. V.; Simmen, K.; Raboisson, P. J. Med. Chem. 2010, 53, 8150. doi: 10.1021/jm101050a
7. [7]
  de Castro, S.; Lozano, A.; Jimeno, M.-L.; Pérez-Pérez, M.-J.; San-Félix, A.; Camarasa, M.-J.; Velázquez, S. J. Org. Chem. 2006, 71, 1407. doi: 10.1021/jo0520588
8. [8]
  Paquette, L. A.; Seekamp, C. K.; Kahane, A. L. J. Org. Chem. 2003, 68, 8614. doi: 10.1021/jo0301954
9. [9]
10. [10]
1. [1]
  Rui Wang , Yang Liang , Julius Rebek Jr. , Yang Yu . Stabilization and detection of labile reaction intermediates in supramolecular containers. Chinese Chemical Letters, 2024, 35(6): 109228-. doi: 10.1016/j.cclet.2023.109228
2. [2]
  Xin Li , Zhen Xu , Donglei Bu , Jinming Cai , Huamei Chen , Qi Chen , Ting Chen , Fang Cheng , Lifeng Chi , Wenjie Dong , Zhenchao Dong , Shixuan Du , Qitang Fan , Xing Fan , Qiang Fu , Song Gao , Jing Guo , Weijun Guo , Yang He , Shimin Hou , Ying Jiang , Huihui Kong , Baojun Li , Dengyuan Li , Jie Li , Qing Li , Ruoning Li , Shuying Li , Yuxuan Lin , Mengxi Liu , Peinian Liu , Yanyan Liu , Jingtao Lü , Chuanxu Ma , Haoyang Pan , JinLiang Pan , Minghu Pan , Xiaohui Qiu , Ziyong Shen , Shijing Tan , Bing Wang , Dong Wang , Li Wang , Lili Wang , Tao Wang , Xiang Wang , Xingyue Wang , Xueyan Wang , Yansong Wang , Yu Wang , Kai Wu , Wei Xu , Na Xue , Linghao Yan , Fan Yang , Zhiyong Yang , Chi Zhang , Xue Zhang , Yang Zhang , Yao Zhang , Xiong Zhou , Junfa Zhu , Yajie Zhang , Feixue Gao , Yongfeng Wang . Recent progress on surface chemistry Ⅰ: Assembly and reaction. Chinese Chemical Letters, 2024, 35(12): 110055-. doi: 10.1016/j.cclet.2024.110055
3. [3]
  Tiantian Long , Hongmei Luo , Jingbo Sun , Fengniu Lu , Yi Chen , Dong Xu , Zhiqin Yuan . Carbonization-engineered ultrafast chemical reaction on nanointerface. Chinese Chemical Letters, 2025, 36(3): 109728-. doi: 10.1016/j.cclet.2024.109728
4. [4]
  Yi Zhang , Biao Wang , Chao Hu , Muhammad Humayun , Yaping Huang , Yulin Cao , Mosaad Negem , Yigang Ding , Chundong Wang . Fe–Ni–F electrocatalyst for enhancing reaction kinetics of water oxidation. Chinese Journal of Structural Chemistry, 2024, 43(2): 100243-100243. doi: 10.1016/j.cjsc.2024.100243
5. [5]
  Xianxu Chu , Lu Wang , Junru Li , Hui Xu . Surface chemical microenvironment engineering of catalysts by organic molecules for boosting electrocatalytic reaction. Chinese Chemical Letters, 2024, 35(8): 109105-. doi: 10.1016/j.cclet.2023.109105
6. [6]
  Kebo Xie , Qian Zhang , Fei Ye , Jungui Dai . A multi-enzymatic cascade reaction for the synthesis of bioactive C-oligosaccharides. Chinese Chemical Letters, 2024, 35(6): 109028-. doi: 10.1016/j.cclet.2023.109028
7. [7]
  Zhao Li , Huimin Yang , Wenjing Cheng , Lin Tian . Recent progress of in situ/operando characterization techniques for electrocatalytic energy conversion reaction. Chinese Chemical Letters, 2024, 35(9): 109237-. doi: 10.1016/j.cclet.2023.109237
8. [8]
  Kunsong Hu , Yulong Zhang , Jiayi Zhu , Jinhua Mai , Gang Liu , Manoj Krishna Sugumar , Xinhua Liu , Feng Zhan , Rui Tan . Nano-engineered catalysts for high-performance oxygen reduction reaction. Chinese Chemical Letters, 2024, 35(10): 109423-. doi: 10.1016/j.cclet.2023.109423
9. [9]
  Zhuwen Wei , Jiayan Chen , Congzhen Xie , Yang Chen , Shifa Zhu . Divergent de novo construction of α-functionalized pyrrole derivatives via coarctate reaction. Chinese Chemical Letters, 2024, 35(12): 109677-. doi: 10.1016/j.cclet.2024.109677
10. [10]
  Guoliang Gao , Guangzhen Zhao , Guang Zhu , Bowen Sun , Zixu Sun , Shunli Li , Ya-Qian Lan . Recent advancements in noble-metal electrocatalysts for alkaline hydrogen evolution reaction. Chinese Chemical Letters, 2025, 36(1): 109557-. doi: 10.1016/j.cclet.2024.109557
11. [11]
  Xuhui Fan , Fan Wang , Mengjiao Li , Faiza Meharban , Yaying Li , Yuanyuan Cui , Xiaopeng Li , Jingsan Xu , Qi Xiao , Wei Luo . Visible light excitation on CuPd/TiN with enhanced chemisorption for catalyzing Heck reaction. Chinese Chemical Letters, 2025, 36(1): 110299-. doi: 10.1016/j.cclet.2024.110299
12. [12]
  Jialin Cai , Yizhe Chen , Ruiwen Zhang , Cheng Yuan , Zeyu Jin , Yongting Chen , Shiming Zhang , Jiujun Zhang . Interfacial Pt-N coordination for promoting oxygen reduction reaction. Chinese Chemical Letters, 2025, 36(2): 110255-. doi: 10.1016/j.cclet.2024.110255
13. [13]
  Yan Guo , Hongtao Bian , Le Yu , Jiani Ma , Yu Fang . Photochemical reaction mechanism of benzophenone protected guanosine at N7 position. Chinese Chemical Letters, 2025, 36(3): 109971-. doi: 10.1016/j.cclet.2024.109971
14. [14]
  Xuan Liu , Qing Li . Tailoring interatomic active sites for highly selective electrocatalytic biomass conversion reaction. Chinese Chemical Letters, 2025, 36(4): 110670-. doi: 10.1016/j.cclet.2024.110670
15. [15]
  Xin Li , Jia-Min Lu , Bo Li , Chen Zhao , Bei-Bei Yang , Li Li . Chiroptical sensing for remote chiral amines via a C–H activation reaction. Chinese Chemical Letters, 2025, 36(5): 110310-. doi: 10.1016/j.cclet.2024.110310
16. [16]
  Haixia Wu , Kailu Guo . Sulfur reduction reaction mechanism elucidated with in situ Raman spectroscopy. Chinese Chemical Letters, 2025, 36(6): 110654-. doi: 10.1016/j.cclet.2024.110654
17. [17]
  Xiao Li , Wanqiang Yu , Yujie Wang , Ruiying Liu , Qingquan Yu , Riming Hu , Xuchuan Jiang , Qingsheng Gao , Hong Liu , Jiayuan Yu , Weijia Zhou . Metal-encapsulated nitrogen-doped carbon nanotube arrays electrode for enhancing sulfion oxidation reaction and hydrogen evolution reaction by regulating of intermediate adsorption. Chinese Chemical Letters, 2024, 35(8): 109166-. doi: 10.1016/j.cclet.2023.109166
18. [18]
  Jing Cao , Dezheng Zhang , Bianqing Ren , Ping Song , Weilin Xu . Mn incorporated RuO₂ nanocrystals as an efficient and stable bifunctional electrocatalyst for oxygen evolution reaction and hydrogen evolution reaction in acid and alkaline. Chinese Chemical Letters, 2024, 35(10): 109863-. doi: 10.1016/j.cclet.2024.109863
19. [19]
  Fenglin Wang , Chengwei Kuang , Zhicheng Zheng , Dan Wu , Hao Wan , Gen Chen , Ning Zhang , Xiaohe Liu , Renzhi Ma . Noble metal clusters substitution in porous Ni substrate renders high mass-specific activities toward oxygen evolution reaction and methanol oxidation reaction. Chinese Chemical Letters, 2025, 36(6): 109989-. doi: 10.1016/j.cclet.2024.109989
20. [20]
  Zizhuo Liang , Fuming Du , Ning Zhao , Xiangxin Guo . Revealing the reason for the unsuccessful fabrication of Li3Zr2Si2PO12 by solid state reaction. Chinese Journal of Structural Chemistry, 2023, 42(11): 100108-100108. doi: 10.1016/j.cjsc.2023.100108

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(750)
HTML views(68)

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