Chinese Journal of Organic Chemistry >
Enantioselective Total Synthesis of (–)-Angustureine
Received date: 2021-01-17
Revised date: 2021-02-05
Online published: 2021-02-26
Supported by
National Natural Science Foundation of China-Henan(U1804283); Postgraduate Education Reform and Quality Improvement Project of Henan Province(YJS2021KC03)
(–)-Angustureine is an important member of the tetrahydroquinoline alkaloid family. Such natural products have attracted the attention of synthetic chemists because of their potential biological activities. Starting from methyl (R)-N-Boc- indoline-2-carboxylate, the enantioselective total synthesis of (–)-angustureine was accomplished in 7 steps. The key step of our synthesis involves a rearrangement ring-expansion reaction.
Lulu Yu , Qunshan Ding , Chuanjun Song , Junbiao Chang . Enantioselective Total Synthesis of (–)-Angustureine[J]. Chinese Journal of Organic Chemistry, 2021 , 41(6) : 2507 -2510 . DOI: 10.6023/cjoc202101025
[1] | Sridharan, V.; Suryavanshi, P. A.; Menéndez, J. C. Chem. Rev. 2011, 111,7157. |
[2] | Katritzky, A. R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52,15031. |
[3] | Jacquemond-Collet, I.; Hannedouche, S.; Fabre, N.; Fourasté, I.; Moulis, C. Phytochemistry 1999, 51,1167. |
[4] | Rakotoson, J. H.; Fabre, N.; Jacquemond-Collet, I.; Hannedouche, S.; Fourasté, I.; Moulis, C. Planta Med. 1998, 64,762. |
[5] | Houghton, P. J.; Woldemariam, T. Z.; Watanabe, Y. Planta Med. 1999, 65,250. |
[6] | Rueping, M.; Antonchick, A. P.; Theissmann, T. Angew. Chem., Int. Ed. 2006, 45,3683. |
[7] | Wang, T.; Zhuo, L.-G.; Li, Z.; Chen, F.; Ding, Z.; He, Y.; Fan, Q.-H.; Xiang, J.; Yu, Z.-X.; Chan, A. S. C. J. Am. Chem. Soc. 2011, 133,9878. |
[8] | Wang, Y.; Liu, Y.; Zhang, D.; Wei, H.; Shi, M.; Wang, F. Angew. Chem., Int. Ed. 2016, 55,3776. |
[9] | Zhou, Y.-G. Acc. Chem. Res. 2007, 40,1357. |
[10] | Rueping, M.; Koenigs, R. M. Chem. Commun. 2011, 47,304. |
[11] | Sun, S.; Nagorny, P. Chem. Commun. 2020, 56,8432. |
[12] | Wang, Z.-J.; Zhou, H.-F.; Wang, T.-L.; He, Y.-M.; Fan, Q.-H. Green Chem. 2009, 11,767. |
[13] | Wang, W.-B.; Lu, S.-M.; Yang, P.-Y.; Han, X.-W.; Zhou, Y.-G. J. Am. Chem. Soc. 2003, 125,10536. |
[14] | Tang, W.; Sun, Y.; Xu, L.; Wang, T.; Fan, Q.; Lam, K.-H.; Chan, A. S. C. Org. Biomol. Chem. 2010, 8,3464. |
[15] | Pappoppula, M.; Cardoso, F. S. P.; Garrett, B. O.; Aponick, A. Angew. Chem., Int. Ed. 2015, 54,15202. |
[16] | Sirvent, J. A.; Foubelo, F.; Yus, M. J. Org. Chem. 2014, 79,1356. |
[17] | Chen, B.-L.; Wang, B.; Lin, G.-Q. J. Org. Chem. 2010, 75,941. |
[18] | Davies, S. G.; Fletcher, A. M.; Houlsby, I. T. T.; Roberts, P. M.; Thomson, J. E.; Zimmer, D. J. Nat. Prod. 2018, 81,2731. |
[19] | Nack, W. A.; He, G.; Zhang, S.-Y.; Lu, C.; Chen, G. Org. Lett. 2013, 15,3440. |
[20] | Cosgrove, S. C.; Plane, J. M.; Marsden, S. P. Chem. Sci. 2018, 9,6647. |
[21] | Sirvent, J. A.; Foubelo, F.; Yus, M. Heterocycles 2014, 88,1163. |
[22] | Patil, N. T.; Wu, H.; Yamamoto, Y. J. Org. Chem. 2007, 72,6577. |
[23] | Xu, C.; Feng, Y.; Li, F.; Han, J.; He, Y.-M.; Fan, Q.-H. Organometallics 2019, 38,3979. |
[24] | Fustero, S.; Moscardo, J.; Jimenez, D.; Perez-Carrion, M. D.; Sanchez-Rosello, M.; Del, Pozo, C. Chem.-Eur. J. 2008, 14,9868. |
[25] | Bentley, S. A.; Davies, S. G.; Lee, J. A.; Roberts, P. M.; Thomson, J. E. Org. Lett. 2011, 13,2544. |
[26] | Guo, Y.; Harutyunyan, S. R. Angew. Chem., Int. Ed. 2019, 58,12950. |
[27] | Satyanarayana, G.; Pflästerer, D.; Helmchen, G. Eur. J. Org. Chem. 2011,6877. |
[28] | Kothandaraman, P.; Foo, S. J.; Chan, P. W. H. J. Org. Chem. 2009, 74,5947. |
[29] | Garg, Y.; Gahalawat, S.; Pandey, S. K. RSC Adv. 2015, 5,38846. |
[30] | Theeraladanon, C.; Arisawa, M.; Nakagawa, M.; Nishida, A. Tetrahedron: Asymmetry 2005, 16,827. |
[31] | Ye, K.-Y.; He, H.; Liu, W.-B.; Dai, L.-X.; Helmchen, G.; You, S.-L. J. Am. Chem. Soc. 2011, 133,19006. |
[32] | Taylor, L. L.; Goldberg, F. W.; Hii, K. K. Org. Biomol. Chem. 2012, 10,4424. |
[33] | Saito, K.; Miyashita, H.; Akiyama, T. Chem. Commun. 2015, 51,16648. |
[34] | Tummatorn, J.; Muñoz, G. D.; Dudley, G. B. Tetrahedron Lett. 2013, 54,1312. |
[35] | Ori, M.; Toda, N.; Takami, K.; Tago, K.; Kogen, H. Angew. Chem., Int. Ed. 2003, 42,2540. |
[36] | Zhang, Q.; Ding, Q.; Song, C.; Chang, J. Chin. J. Org. Chem. 2018, 38,221(in Chinese). |
[36] | (张倩倩, 丁群山, 宋传君, 常俊标, 有机化学, 2018, 38,221.) |
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