Chinese Journal of Organic Chemistry >
Advances in the Catalytic Asymmetric Synthesis of Chiral Spiroketals
Received date: 2022-05-01
Revised date: 2022-06-13
Online published: 2022-06-29
Supported by
National Natural Science Foundation of China(22171081)
As an unique spiro skeleton, spiroketals are ubiquitous motifs in many natural products, biologically active molecules, and privileged chiral ligands. The development of efficient synthetic methods for the preparation of spiroketals has long been a hot research topic in organic synthesis. In particular, the remarkable advances regarding the catalytic asymmetric synthesis of chiral spiroketals have been achieved over the past decade. The progress in the field of catalytic asymmetric synthesis of chiral spiroketals is summarized according to the reaction types. The future development direction of this field is also prospected.
Key words: asymmetric catalysis; enantioselectivity; spiroketals
Hui Yan , Man Zhang , Lin Li , Teng Hu , Wulin Yang . Advances in the Catalytic Asymmetric Synthesis of Chiral Spiroketals[J]. Chinese Journal of Organic Chemistry, 2022 , 42(11) : 3640 -3657 . DOI: 10.6023/cjoc202205001
| [1] | (a) Zhu, S.-F.; Zhou, Q.-L. In Privileged Chiral Ligands and Catalysts, Ed.: Zhou, Q.-L., Wiley-VCH, Weinheim, 2011, pp. 137-170. |
| [1] | (b) Ding, K.; Han, Z.; Wang, Z. Chem. Asian J. 2009, 4, 32. |
| [1] | (c) Ramon, R. Chem. Soc. Rev. 2012, 41, 1060. |
| [2] | (a) Perron, F.; Albizati, K. F. Chem. Rev. 1989, 89, 1617. |
| [2] | (b) Wilsdorf, M.; Reissig, H. U. Angew. Chem., Int. Ed. 2012, 51, 9486. |
| [3] | (a) Aho, J. E.; Pihko, P. M.; Rissa, T. K. Chem. Rev. 2005, 105, 4406. |
| [3] | (b) Sperry, J.; Wilson, Z. E.; Rathwell, D. C. K.; Brimble, M. A. Nat. Prod. Rep. 2010, 27, 1117. |
| [3] | (c) Atkinson, D. J.; Brimble, M. A. Nat. Prod. Rep. 2015, 32, 811. |
| [3] | (d) Zhang, F.-M.; Zhang, S.-Y.; Tu, Y.-Q. Nat. Prod. Rep. 2018, 35, 75. |
| [3] | (e) Gillard, R. M.; Brimble, M. A. Org. Biomol. Chem. 2019, 17, 8272. |
| [4] | Liu, W.-Z.; Ma, L.-Y.; Liu, D.-S.; Huang, Y.-L.; Wang, C.-H.; Shi, S.-S.; Pan, X.-H.; Song, X.-D.; Zhu, R.-X. Org. Lett. 2014, 16, 90. |
| [5] | Fujimoto, H.; Nozawa, M.; Okuyama, E.; Ishibashi, M. Chem. Pharm. Bull. 2002, 50, 330. |
| [6] | Li, J.; Li, L.; Si, Y.; Jiang, X.; Guo, L.; Che, Y. Org. Lett. 2011, 13, 2670. |
| [7] | Stierle, A. A.; Stierle, D. B.; Kelly, K. J. Org. Chem. 2006, 71, 5357; |
| [8] | Zhuravleva, O. I.; Sobolevskaya, M. P.; Afiyatullov, S. S.; Kirichuk, N. N.; Denisenko, V. A.; Dmitrenok, P. S.; Yurchenko, E. A.; Dyshlovoy, S. A. Mar. Drugs 2014, 12, 5930. |
| [9] | Namikoshi, M.; Kobayashi, H.; Yoshimoto, T.; Meguro, S. Chem. Lett. 2000, 29, 308. |
| [10] | (a) Twiner, M. J.; Doucette, G. J.; Pang, Y.; Fang, C.; Forsyth, C. J.; Miles, C. O. Mar. Drugs 2016, 14, 207. |
| [10] | (b) Fu, L.-L.; Zhao, X.-Y.; Ji, L.-D.; Xu, J. Toxicon 2019, 160, 1. |
| [11] | Reddy, C. R.; Srikanth, B.; Dilipkumar, U.; Rao, K. M. V.; Jagadeesh, B. Eur. J. Org. Chem. 2013, 525. |
| [12] | Trost, B. M.; Weiss, A. H. Angew. Chem., Int. Ed. 2007, 46, 7664. |
| [13] | Uckun, F. M.; Mao, C.; Vassilev, A. O.; Huang, H.; Jan, S.-T. Bioorg. Med. Chem. Lett. 2000, 10, 541. |
| [14] | Scheepstra, M.; Andrei, S. A.; Unver, M. Y.; Hirsch, A. K. H.; Leysen, S.; Ottmann, C.; Brunsveld, L.; Milroy, L.-G. Angew. Chem., Int. Ed. 2017, 56, 5480. |
| [15] | (a) Wang, X.; Ding, K. Chin. J. Chem. 2018, 36, 899. |
| [15] | (b) Wang, X.; Han, Z.; Wang, Z.; Ding, K. Acc. Chem. Res. 2021, 54, 668. |
| [15] | (c) Li, J.; Chen, G.; Wang, Z.; Zhang, R.; Zhang, X.; Ding, K. Chem. Sci. 2011, 2, 1141. |
| [16] | (a) Argüelles, A. J.; Sun, S.; Budaitis, B. G.; Nagorny, P. Angew. Chem., Int. Ed. 2018, 57, 5325. |
| [16] | (b) Huang, J.; Hong, M.; Wang, C.-C.; Kramer, S.; Lin, G.-Q.; Sun, X.-W. J. Org. Chem. 2018, 83, 12838. |
| [17] | (a) Rizzacasa, M. A.; Pollex, A. Org. Biomol. Chem. 2009, 7, 1053. |
| [17] | (b) Raju, B. R.; Saikia, A. K. Molecules 2008, 13, 1942. |
| [17] | (c) Sperry, J.; Liu, Y.-C.; Brimble, M. A. Org. Biomol. Chem. 2010, 8, 29. |
| [17] | (d) Palmes, J. A.; Aponick, A. Synthesis 2012, 44, 3699. |
| [17] | (e) Quach, R.; Chorley, D. F.; Brimble, M. A. Org. Biomol. Chem. 2014, 12, 7423. |
| [17] | (f) Quach, R.; Furkert, D. P.; Brimble, M. A. Org. Biomol. Chem. 2017, 15, 3098. |
| [18] | ?ori?, I.; List, B. Nature 2012, 483, 315. |
| [19] | (a) Sun, Z.; Winschel, G. A.; Borovika, A.; Nagorny, P. J. Am. Chem. Soc. 2012, 134, 8074. |
| [19] | (b) Khomutnyk, Y. Y.; Argu?elles, A. J.; Winschel, G. A.; Sun, Z.; Zimmerman, P. M.; Nagorny, P. J. Am. Chem. Soc. 2016, 138, 444. |
| [20] | Wang, X.; Han, Z.; Wang, Z.; Ding, K. Angew. Chem., Int. Ed. 2012, 51, 936; |
| [21] | Wang, X.; Guo, P.; Wang, X.; Wang, Z.; Ding, K. Adv. Synth. Catal. 2013, 355, 2900. |
| [22] | Liu, N.; Zhu, W.; Yao, J.; Yin, L.; Lu, T.; Dou, X. ACS Catal. 2020, 10, 2596. |
| [23] | Han, X.; Floreancig, P. E. Angew. Chem., Int. Ed. 2014, 53, 11075. |
| [24] | Rexit, A. A.; Mailikezati, M. Tetrahedron Lett. 2015, 56, 2651. |
| [25] | Yoneda, N.; Fukata, Y.; Asano, K.; Matsubara, S. Angew. Chem., Int. Ed. 2015, 54, 15497. |
| [26] | Xue, J.; Zhang, H.; Tian, T.; Yin, K.; Liu, D.; Jiang, X.; Li, Y.; Jin, X.; Yao, X. Adv. Synth. Catal. 2016, 358, 370. |
| [27] | Hamilton, J. Y.; Ro?ssler, S. L.; Carreira, E. M. J. Am. Chem. Soc. 2017, 139, 8082. |
| [28] | R?ssler, S. L.; Schreib, B. S.; Ginterseder, M.; Hamilton, J. Y.; Carreira, E. M. Org. Lett. 2017, 19, 5533. |
| [29] | Midya, A.; Maity, S.; Ghorai, P. Chem. Eur. J. 2017, 23, 11216. |
| [30] | Roy, T. K.; Gorad, S. S.; Ghorai, P. Org. Lett. 2022, 24, 1889. |
| [31] | Reddy, R. R.; Panda, S.; Ghorai, P. J. Org. Chem. 2019, 84, 5357. |
| [32] | Zheng, T.; Wang, X.; Ng, W.-H.; Tse, Y.-L. S.; Yeung, Y.-Y. Nat. Catal. 2020, 3, 993. |
| [33] | Xu, S.; Huang, A.; Yang, Y.; Wang, Y.; Zhang, M.; Sun, Z.; Zhao, M.; Wei, Y.; Li, G.; Hong, L. Org. Lett. 2022, 24, 2978. |
| [34] | Hilby, K. M.; Denmark, S. E. J. Org. Chem. 2021, 86, 14250. |
| [35] | Audrain, H.; Thorhauge, J.; Hazell, R. G.; J?rgensen, K.-A. J. Org. Chem. 2000, 65, 4487. |
| [36] | Yu, S.; Gao, L.; Yan, Y.; Yin, Z.; Shang, Y. Chin. J. Org. Chem. 2021, 41, 582. (in Chinese) |
| [36] | ( 余述燕, 高丽宏, 闫溢哲, 尹志刚, 商永嘉, 有机化学 2021, 41, 582.) |
| [37] | Wu, H.; He, Y.-P.; Gong, L.-Z. Org. Lett. 2013, 15, 460. |
| [38] | Cala, L.; Mendoza, A.; Fa?anás, F. J.; Rodríguez, F. Chem. Commun. 2013, 49, 2715. |
| [39] | (a) Wang, X.; Dong, S.; Yao, Z.; Feng, L.; Daka, P.; Wang, H.; Xu, Z. Org. Lett. 2014, 16, 22. |
| [39] | (b) Liang, M.; Zhang, S.; Jia, J.; Tung, C.-H.; Wang, J.; Xu, Z. Org. Lett. 2017, 19, 2526. |
| [39] | (c) Teng, Q.; Qi, J.; Zhou, L.; Xu, Z.; Tung, C.-H. Org. Chem. Front. 2018, 5, 990. |
| [39] | (d) Mao, W.; Lin, S.; Zhang, L.; Lu, H.; Jia, J.; Xu, Z. Org. Chem. Front. 2020, 7, 856. |
| [40] | Li, J.; Lin, L.; Hu, B.; Lian, X.; Wang, G.; Liu, X.; Feng, X. Angew. Chem., Int. Ed. 2016, 55, 6075. |
| [41] | Gong, J.; Wan, Q.; Kang, Q. Adv. Synth. Catal. 2018, 360, 4031. |
| [42] | (a) Yang, W.-L.; Shang, X.-Y.; Luo, X.; Deng, W.-P. Angew. Chem., Int. Ed. 2022, 61, e202203661. |
| [42] | (b) Yuen, D.-Y.; Yang, S.-H.; Brimble, M. A. Angew. Chem., nt. Ed. 2011, 50, 8350. |
| [43] | Yang, W.-L.; Wang, Y.-L.; Li, W.; Gu, B.-M.; Wang, S.-W.; Luo, X.; Tian, B.-X.; Deng, W.-P. ACS Catal. 2021, 11, 12557. |
| [44] | Chen, J.-R.; Hu, X.-Q.; Xiao, W.-J. Angew. Chem., Int. Ed. 2014, 53, 4038. |
| [45] | (a) Wang, D.; Liu, S.; Lan, X.-C.; Paniagua, A.; Hao, W.-J.; Li, G.; Tu, S.-J.; Jiang, B. Adv. Synth. Catal. 2017, 359, 3186. |
| [45] | (b) Liu, S.; Chen, K.; Lan, X.-C.; Hao, W.-J.; Li, G.; Tu, S.-J.; Jiang, B. Chem. Commun. 2017, 53, 10692. |
| [45] | (c) Liu, S.; Lan, X.-C.; Chen, K.; Hao, W.-J.; Li, G.; Tu, S.-J.; Jiang, B. Org. Lett. 2017, 19, 3831. |
| [45] | (d) Qiu, J.-K.; Hao, W.-J.; Li, G.; Jiang, B. Adv. Synth. Catal. 2018, 360, 1182. |
| [45] | (e) Ji, C.-L.; Pan, Y.; Geng, F.-Z.; Hao, W.-J.; Tu, S.-J.; Jiang, B. Org. Chem. Front. 2019, 6, 474. |
| [46] | Ge, S.; Cao, W.; Kang, T.; Hu, B.; Zhang, H.; Su, Z.; Liu, X.; Feng, X. Angew. Chem., Int. Ed. 2019, 58, 4017. |
| [47] | Dong, K.; Gurung, R.; Xu, X.; Doyle, M. P. Org. Lett. 2021, 23, 3955. |
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