Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution for the Construction of Carbocyclic N3-Purine Nucleosides

doi:10.6023/cjoc201907053

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (2): 376-383.DOI: 10.6023/cjoc201907053 Previous Articles Next Articles

通过不对称氢转移/动态动力学拆分合成碳环N³-嘌呤核苷

张齐英, 张一铭, 郝二军, 白娟, 渠桂荣, 郭海明

河南师范大学化学化工学院绿色化学介质与反应教育部重点实验室精细化学品绿色制造河南省协同创新中心河南省有机功能分子与药物创新重点实验室河南新乡 453007

收稿日期:2019-07-30 修回日期:2019-09-30 发布日期:2019-10-25
通讯作者: 郭海明 E-mail:ghm@htu.edu.cn
基金资助:
国家自然科学基金（Nos.21602045，U1604283）和高等学校学科创新引智计划（111计划，No.D17007）资助项目.

Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution for the Construction of Carbocyclic N³-Purine Nucleosides

Zhang Qiying, Zhang Yiming, Hao Erjun, Bai Juan, Qu Guirong, Guo Haiming

Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007

Received:2019-07-30 Revised:2019-09-30 Published:2019-10-25
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21602045, U1604283), and the Overseas Expertise Introduction Project for Discipline Innovation (111 Project, No. D17007).

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Abstract

N³-Purine nucleoside can be employed as a potent dual inhibitor to inhibit viruses more effectively because it could be possibly recognized by both purine-and pyrimidine-metabolizing enzymes. Herein, an asymmetric transfer hydrogenation via dynamic kinetic resolution of rac-α-(purin-3-yl)cyclopentones has been developed to produce a wide range of carbocyclic N³-purine nucleosides in high yields and excellent stereoselectivities. Moreover, the catalytic system was suitable for rac-α-pyrimidinyl cyclopentones. With additional transformations, several 2'-F-, AcS-, N₃-modified carbocyclic nucleosides could be obtained with good to excellent yields and excellent enantioselectivities.

Key words: carbocyclic nucleosides, dual inhibitors, dynamic kinetic resolution, asymmetric transfer hydrogenation

Cite this article

Zhang Qiying, Zhang Yiming, Hao Erjun, Bai Juan, Qu Guirong, Guo Haiming. Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution for the Construction of Carbocyclic N³-Purine Nucleosides[J]. Chinese Journal of Organic Chemistry, 2020, 40(2): 376-383.

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[1] (a) Zhou, H.; Zeng, X.; Ding, L.; Xie, Y.; Zhong, G. Org. Lett. 2015, 17, 2385.
(b) Trost, B. M.; Madsen, R.; Guile, S. D.; Brown, B. J. Am. Chem. Soc. 2000, 122, 5947.
(c) Kakuda, T. N. Clin. Ther. 2000, 22, 685.
(d) Boutureira, O.; Matheu, M. I.; Díaz, Y.; Castillón, S. Chem. Soc. Rev. 2013, 42, 5056.
(e) Forsman, J. J.; Leino, R. Chem. Rev. 2011, 111, 3334.
(f) Lebreton, J.; Escudier, J.-M.; Arzel, Len, C. Chem. Rev. 2010, 110, 3371.
(g) Amblard, F.; Cho, J. H.; Schinazi, R. F. Chem. Rev. 2009, 109, 4207.
(h) Liu, Y.; Guo, X.; Bai, P. Chin. J. Org. Chem. 2014, 34, 2202(in Chinese). (刘亚君, 郭翔海, 白鹏, 有机化学, 2014, 34, 2202.)
(i) Fan, X.-S; Zhang, X.-Y.; Wang, X.; Qu, G.-R. Chin. J. Org. Chem. 2008, 28, 1888(in Chinese). (范学森, 张新迎, 王霞, 渠桂荣, 有机化学, 2008, 28, 1888.)
[2] (a) Barral, K.; Courcambeck, J.; Pèpe, G.; Balzarini, J.; Neyts, J.; Clercq, E. D.; Camplo, M. J. Med. Chem. 2005, 48, 450.
(b) Keane, S. J.; Ford, A.; Mullins, N. D.; Maguire, N. M.; Legigan, T.; Balzarini, J.; Maguire, A. R. J. Org. Chem. 2015, 80, 2479.
(c) Gai, X.; Song, W.; Heng, S.; Yang, W. Chin. J. Integr. Tradit. West. Med. Liver Dis. 2005, 15, 50(in Chinese). (盖欣, 宋万玲, 桓树学, 杨文东, 中西医结合肝病杂志, 2005, 15, 50.)
[3] (a) Hu, L.; Ren, Y.; Ramström, O. J. Org. Chem. 2015, 80, 8478.
(b) Singh, U. S.; Mishra, R. C.; Shankar, R.; Chu, C. K. J. Org. Chem. 2014, 79, 3917.
(c) Caso, M. F.; D'Alonzo, D.; D'Errico, S.; Palumbo, G.; Guaragna, A. Org. Lett. 201517, 2626.
[4] (a) Silverman, R. B. The Organic Chemistry of Drug Design and Drug Action, Elsevier, Evanston, 2004.
(b) Kompis, I. M.; Islam, K.; Then, R. L. Chem. Rev. 2005, 105, 583.
(c) Lyon, M. A.; Ducruet, A. P.; Wipf, P.; Lazo, J. S. Nat. Rev. Drug Disc. 2002, 1, 961.
(d) Gangjee, A.; Li, W.; Yang, J.; Kisliuk, R. L. J. Med. Chem. 2008, 51, 68.
[5] (a) Jeong, L. S.; Lee, J. A. Antiviral Chem. Chemother. 2004, 15, 235.
(b) Liu, Y.; Guo, X.; Bai, P. Chin. J. Org. Chem. 2014, 34, 2202.
(c) Boutureira, O.; Matheu, M. I.; Díaz, Y.; Castillón, S. Chem. Soc. Rev. 2013, 42, 5056.
[6] (a) Xie, M.-S.; Wang, Y.; Li, J.-P.; Du, C.; Zhang, Y.-Y.; Hao, E.-J.; Zhang, Y.-M.; Qu, G.-R.; Guo, H.-M. Chem. Commun. 2015, 51, 12451.
(b) Huang, K.-X.; Xie, M.-S.; Zhang, Q.-Y.; Niu, H.-Y.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2018, 20, 5398.
(c) Wang, J.; Zhang, Q.-Y.; Xie, M.-S.; Wang, D.-C.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2018, 20, 6578.
(d) Gao, Y.-W.; Niu, H.; Zhang, Q.-Y.; Xie, M.; Qu, G.; Guo, H. Adv. Synth. Catal. 2018, 360, 2813.
[7] (a) Bhat, B.; Neelima, N. J.; Leonard, H.; Robinson, A.; Wang, H.-J. J. Am. Chem. Soc. 1996, 118, 3065.
(b) Leonard, N. J.; Laursenf, R. A. Biosci., Biotechnol., Biochem. 1965, 4, 354.
[8] (a) Sadler, J. M.; Mosley, S. L.; Dorgan, K. M.; Zhou, Z. S.; Seley-Radtke, K. L. Bioorg. Med. Chem. 2009, 17, 5520.
(b) Jiang, M. X.-W.; Warshakoon, N. C.; Miller, M. J. J. Org. Chem. 2005, 70, 2824.
[9] (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029.
(b) Liu, S.; Xie, J.-H.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem. 2007, 119, 7650; Angew. Chem., Int. Ed. 2007, 46, 7506.
(c) Liu, S.; Xie, J.-H.; Li, W.; Kong, W.-L.; Wang, L.-X.; Zhou, Q.-L. Org. Lett. 2009, 11, 4994.
(d) Zhou, Q.; Xie, J.; Zhu, S.; Wang, L. Tianjin Sci. Technol. 2014, 41, 11(in Chinese). (周其林, 谢建华, 朱守非, 王立新, 天津科技, 2014, 41, 11.)
[10] (a) Zhang, Q.; Ma, B.-W.; Wang, Q.-.Q.; Wang, X.-X.; Hu, X.; Xie, M.-S.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2014, 16, 2014.
(b) Vyas, V. K.; Bhanage, B. M. Org. Lett. 2016, 18, 6436.
(c) Matsunami, A.; Ikeda, M.; Nakamura, H.; Yoshida, M.; Kuwata, S.; Kayaki, Y. Org. Lett. 2018, 20, 5213.
(d) Vyas, V. K.; Bhanage, B. M. Asian J. Org. Chem. 2018, 7, 346.
(e) Liu, Q.; Wang, C.; Zhou, H.; Wang, O.; Lv, J.; Cao, Lu; Fu, Y. Org. Lett. 2018, 20, 971.
[11] (a) Zhang, Y.-M.; Zhang, Q.-Y.; Wang, D.-C.; Xie, M.-S.; Qu, G.-R.; Guo, H.-M. Org. Lett. 2019, 21, 2998.
(b) Sun, H.-L.; Chen, F.; Xie, M.-S.; Guo, H.-M.; Qu, G.-R.; He, Y.-M.; Fan, Q.-H. Org. Lett. 2016, 18, 2260.
[12] (a) Chan, A. S. C.; Pluth, J. J.; Halpern, J. J. Am. Chem. Soc. 1980, 102, 5952.
(b) Miyashita, A.; Yasuda, A.; Takaya, H.; Toriumi, K.; Ito, T.; Souchi, T.; Noyori, R. J. Am. Chem. Soc. 1980, 102, 7932.

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通过不对称氢转移/动态动力学拆分合成碳环N³-嘌呤核苷

Asymmetric Transfer Hydrogenation via Dynamic Kinetic Resolution for the Construction of Carbocyclic N³-Purine Nucleosides

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通过不对称氢转移/动态动力学拆分合成碳环N3-嘌呤核苷