C-3位五元螺环吲哚酮衍生物合成方法研究进展
收稿日期: 2021-04-04
修回日期: 2021-05-03
网络出版日期: 2021-06-02
基金资助
国家自然科学基金(22071113); 天津市重点研发计划(19YFZCSN00240)
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)
刘奕彤 , 张茜苑 , 苗志伟 . C-3位五元螺环吲哚酮衍生物合成方法研究进展[J]. 有机化学, 2021 , 41(10) : 3965 -3982 . DOI: 10.6023/cjoc202104008
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
[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. |
/
〈 |
|
〉 |