Chinese Journal of Organic Chemistry >
Research Progress on the Synthetic Method of Five-Membered Spirooxindole Derivatives at C-3 Position
Received date: 2021-04-04
Revised date: 2021-05-03
Online published: 2021-06-02
Supported by
National Natural Science Foundation of China(22071113); Key Technologies R & D Program of Tianjin City(19YFZCSN00240)
As the core skeleton structure of many drugs and natural products, spirooxindole derivatives have a wide range of applications in the field of biology and medicine. Efficient synthesis of spirooxindole derivatives with high enantioselectivity and diastereoselectivity has gained much attention in organic chemical community. In this paper, the asymmetric synthetic methods for C-3 five-membered spirooxindoles by catalytic intramolecular reactions, intermolecular reactions and three- component reactions are reviewed. The future development direction of this field is also prospected.
Key words: spirooxindoles; synthetic method; asymmetric synthesis
Yitong Liu , Xiyuan Zhang , Zhiwei Miao . Research Progress on the Synthetic Method of Five-Membered Spirooxindole Derivatives at C-3 Position[J]. Chinese Journal of Organic Chemistry, 2021 , 41(10) : 3965 -3982 . DOI: 10.6023/cjoc202104008
[1] | Mei, G.-J.; Shi, F. Chem. Commun. 2018, 54, 6607. |
[2] | Cui, C.-B.; Kakeya, H.; Osada, H. Tetrahedron 1996, 52, 12651. |
[3] | Cui, C.-B.; Kakeya, H.; Osada, H. J. Antibiot. 1996, 49, 832. |
[4] | Watson, A. F.; Liu, J.-F.; Bennaceur, K.; Drummond, C. J.; Endicott, J. A.; Golding, B. T.; Griffin, R. J.; Haggerty, K.; Lu, X.-H.; McDonnell, J. M.; Newell, D. R.; Noble, M. E. M.; Revill, C. H.; Riedinger, C.; Xu, Q.; Zhao, Y.; Lunec, J.; Hardcastle, L. R. Bioorg. Med. Chem. Lett. 2011, 21, 5916. |
[5] | Zhou, J.-Y.; Zhou, S.-W. J. Ethnopharmacol. 2010, 132, 15. |
[6] | Xiao, Y.-L.; Zhou, Y.; Wang, J.; Wang, J.-X.; Liu, H. Chin. J. Org. Chem. 2015, 35, 2035. (in Chinese) |
[6] | (肖永龙, 周宇, 王江, 王进欣, 柳红, 有机化学, 2015, 35, 2035.) |
[7] | Ohmatsu, K.; Ando, Y.; Nakashima, T.; Ooi, T. Chem 2016, 1, 802. |
[8] | Yin, B.-L.; Lai, J.-Q.; Zhang, Z.-R.; Jiang, H.-F. Adv. Synth. Catal. 2011, 353, 1961. |
[9] | Yin, B.-L.; Huang, L.; Zhang, X.-Y.; Ji, F.-H.; Jiang, H.-F. J. Org. Chem. 2012, 77, 6365. |
[10] | Yin, B.-L.; Huang, L.; Wang, X.-J.; Liu, J.-C.; Jiang, H.-F. Adv. Synth. Catal. 2013, 355, 370. |
[11] | Yin, X.-P.; Zeng, X.-P.; Liu, Y.-L.; Liao, F.-M.; Yu, J.-S.; Zhou, F.; Zhou, J. Angew. Chem., Int. Ed. 2014, 53, 13740. |
[12] | Nakagawa, M.; Matsuki, K.; Hasegawa, K.; Hino, T. J. Chem. Soc., Chem. Commun. 1982, 742. |
[13] | Xu, J.; Liang, L.-X.; Zheng, H.-H.; Chi, Y.-R.; Tong, R.-B. Nat. Commun. 2019, 10, 4754. |
[14] | Li, G.-F.; Huang, L.-W.; Xu, J.-C.; Sun, W.-S.; Xie, J.-Q.; Hong, L.; Wang, R. Adv. Synth. Catal. 2016, 358, 2873. |
[15] | Wang, D.-G.; Lu, X.-B.; Sun, S.-H.; Yu, H.-B.; Su, H.-M.; Wu, Y.-Z.; Zhong, F.-R. Eur. J. Org. Chem. 2019, 6028. |
[16] | Liu, J.-C.; Peng, H.; Lu, L.; Xu, X.-B.; Jiang, H.-F.; Yin, B.-L. Org. Lett. 2016, 18, 6440. |
[17] | Liu, J.-C.; Xu, X.-B.; Li, J.-Y.; Liu, B.; Jiang, H.-F.; Yin, B.-L. Chem. Commun. 2016, 52, 9550. |
[18] | Liu, J.-C.; Peng, H.; Yang, Y.-J.; Jiang, H.-F.; Yin, B.-L. J. Org. Chem. 2016, 81, 9695. |
[19] | Chen, J.-Q.; Wei, Y.-L.; Xu, G.-Q.; Liang, Y.-M.; Xu, P.-F. Chem. Commun. 2016, 52, 6455. |
[20] | Ratushnyy, M.; Kvasovs, N.; Sarkar, S.; Gevorgyan, V. Angew. Chem., Int. Ed. 2020, 59, 10316. |
[21] | Ying, A.-G.; Wu, C.-L.; Fu, Y.-Q.; Ren, S.-B.; Liang, H.-D. Chin. J. Org. Chem. 2012, 32, 1587. (in Chinese) |
[21] | (应安国, 武承林, 付永前, 任世斌, 梁华定, 有机化学, 2012, 32, 1587.) |
[22] | Sankar, M. G.; Castro, M. G.; Golz, C.; Strohmann, C.; Kumar, K.; Ihsar, M. P. S. Angew. Chem., Int. Ed. 2016, 55, 9709. |
[23] | Feng, J.-X.; Huang, Y. Chem. Commun. 2019, 55, 14011. |
[24] | Yu, C.-B.; Zheng, W.-P.; Zhan, J.-C.; Sun, Y.-C.; Miao, Z.-W. RSC Adv. 2014, 4, 63246. |
[25] | Zhang, J.-Y.; Cheng, C.; Wang, D.; Miao, Z.-W. J. Org. Chem. 2017, 82, 10121. |
[26] | Lin, Y.; Du, D.-M. Chin. J. Org. Chem. 2020, 40, 3214. (in Chinese) |
[26] | (林晔, 杜大明, 有机化学, 2020, 40, 3214.) |
[27] | Duan, S.-W.; Li, Y.; Liu, Y.-Y.; Zou, Y.-Q.; Shi, D.-Q.; Xiao, W.-J. Chem. Commun. 2012, 48, 5160. |
[28] | Ding, L.-Z.; Zhong, T.-S.; Wu, H.; Wang, Y.-M. Eur. J. Org. Chem. 2014, 5139. |
[29] | Buxton, C. S.; Blakemore, D. C.; Bower, J. F. Angew. Chem., Int. Ed. 2017, 56, 13824. |
[30] | Zhou, P.-F.; Cai, Y.-F.; Lin, L.-L.; Lian, X.-J.; Xia, Y.; Liu, X.-H.; Feng, X.-M. Adv. Synth. Catal. 2015, 357, 695. |
[31] | Tan, W.; Zhu, X.-T.; Zhang, S.; Xing, G.-J.; Zhu, R.-Y.; Shi, F. RSC Adv. 2013, 3, 10875. |
[32] | Yu, B.; Sun, X.-N. Shi, X.-J.; Qi, P.-P.; Zheng, Y.-C.; Yu, D.-Q.; Liu, H.-M. Steroids 2015, 102, 92. |
[33] | Shi, F.; Tao, Z.-L.; Luo, S.-W.; Tu, S.-J.; Gong, L.-Z. Chem.-Eur. J. 2012, 18, 6885. |
[34] | Guo, C.; Song, J.; Gong, L.-Z. Org. Lett. 2013, 15, 2676. |
[35] | Yang, J.; Liu, X.-W.; Wang, D.-D.; Tian, M.-Y.; Han, S.-N.; Feng, T.-T.; Liu, X.-L.; Mei, R.-Q.; Zhou, Y. Tetrahedron 2016, 72, 8523. |
[36] | Wu, M.-Y.; He, W.-W.; Liu, X.-Y.; Tan, B. Angew. Chem., Int. Ed. 2015, 54, 9409. |
[37] | Salahi, F.; Taghizadeh, M. J.; Arvinnezhad, H.; Moemeni, M.; Jadidi, K.; Notas, B. Tetrahedron Lett. 2014, 55, 1515. |
[38] | Miao, Y.-H.; Hua, Y.-Z.; Wang, M.-C. Org. Biomol. Chem. 2019, 17, 7172. |
/
〈 |
|
〉 |