Citation: Zhiguo Zhang, Xiaoqing Song, Guofeng Li, Xiang Li, Dan Zheng, Xuna Zhao, Huanran Miao, Guisheng Zhang, Lantao Liu. Synthesis of polycyclic spiro-fused indolines via IBX-mediated cascade cyclization[J]. Chinese Chemical Letters, ;2021, 32(4): 1423-1426. doi: 10.1016/j.cclet.2020.11.001 shu

Synthesis of polycyclic spiro-fused indolines via IBX-mediated cascade cyclization

Zhiguo Zhang ^{a, *,} ,
Xiaoqing Song ^a ,
Guofeng Li ^a ,
Xiang Li ^a ,
Dan Zheng ^b ,
Xuna Zhao ^a ,
Huanran Miao ^a ,
Guisheng Zhang ^{a, *,} ,
Lantao Liu ^c

a.
Henan Key Laboratory of Organic Functional Molecule 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 453007, China
b.
Quality and Technique Supervision, Inspection and Testing Center of Xuchang City, Xuchang 461000, China
c.
The College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000, China

zhangzg@htu.edu.cn

zgs6668@yahoo.com

Received Date: 6 September 2020
Revised Date: 20 October 2020
Accepted Date: 2 November 2020
Available Online: 2 November 2020

Figures(4)

We report a 2-iodoxybenzoic acid (IBX)-mediated intarmolecular oxidative spiro-fused tandem cyclization reaction of tryptophan analogs bearing an N-arylamides side-chain to rapidly afford polycyclic spiroindolines featuring multiple stereocenters including a quaternary stereocenters under mild reaction conditions. Among them, a novelty azaphosphol idine-containing spiroindoline compound is synthesized for the first time. It may open the door to azaphos pholidine-containing spiroindoline compound of potential interest in synthetic and medicinal chemistry. A plausible mechanism is proposed.
- Spiro-indolines,
- Fused indolines,
- 2-Iodoxybenzoic acid,
- Hypervalent iodine reagents
1. [1]
  M. Zhu, Y. Han, C. Liu, W. Ma, C.G. Yan, Chin. Chem. Lett. 31(2020) 1554-1557. doi: 10.1016/j.cclet.2019.12.028
2. [2]
  Y. Sasaki, D. Kato, D.L. Boger, J. Am. Chem. Soc. 132(2010) 13533-13544. doi: 10.1021/ja106284s
3. [3]
  J.W. Blunt, B.R. Copp, M.H.G. Munro, P.T. Northcote, M.R. Prinsep, Nat. Prod. Rep. 23(2006) 26-78.
4. [4]
  W. Gul, M.T. Hamann, Life Sci. 78(2005) 442-453. doi: 10.1016/j.lfs.2005.09.007
5. [5]
  P.W. Xu, J.S. Yu, C. Chen, et al., ACS Catal. 9(2019) 1820-1882. doi: 10.1021/acscatal.8b03694
6. [6]
  L. Kortekaas, W.R. Browne, Chem. Soc. Rev. 48(2019) 3406-3424. doi: 10.1039/C9CS00203K
7. [7]
  R. Dalpozzo, G. Bartoli, G. Bencivenni, Chem. Soc. Rev. 41(2012) 7247-7290. doi: 10.1039/c2cs35100e
8. [8]
  B.M. Trost, M.K. Brennan, Synthesis 2009(2009) 3003-3025. doi: 10.1055/s-0029-1216975
9. [9]
  C. Marti, Erick M. Carreira, Eur. J. Org. Chem. 2003(2003) 2209-2219. doi: 10.1002/ejoc.200300050
10. [10]
  J.Q. Zhao, X.J. Zhou, Y. Zhou, et al., Org. Lett. 20(2018) 909-912. doi: 10.1021/acs.orglett.7b03667
11. [11]
  G.S. Singh, Z.Y. Desta, Chem. Rev. 112(2012) 6104-6155. doi: 10.1021/cr300135y
12. [12]
  J. Bariwal, L.G. Voskressensky, E.V. Van der Eycken, Chem. Soc. Rev. 47(2018) 3831-3848. doi: 10.1039/C7CS00508C
13. [13]
  L.J. Zhang, Y. Wang, X.Q. Hu, P.F. Xu, Chem. Asian J. 11(2016) 834-838. doi: 10.1002/asia.201600013
14. [14]
  J.Y. Du, C. Zeng, X.J. Han, et al., J. Am. Chem. Soc. 137(2015) 4267-4273. doi: 10.1021/jacs.5b01926
15. [15]
  J. Pereira, M. Barlier, C. Guillou, Org. Lett. 9(2007) 3101-3103. doi: 10.1021/ol0712576
16. [16]
  J.M. Saya, T.R. Roose, J.J. Peek, et al., Angew. Chem. Int. Ed. 57(2018) 15232-15236. doi: 10.1002/anie.201809678
17. [17]
  K. Sun, Y. Li, R. Feng, et al., J. Org. Chem. 85(2020) 1001-1008. doi: 10.1021/acs.joc.9b02941
18. [18]
  W. He, J. Hu, P. Wang, et al., Angew. Chem. Int. Ed. 57(2018) 3806-3809. doi: 10.1002/anie.201800567
19. [19]
  W. Chen, X.D. Yang, W.Y. Tan, et al., Angew. Chem. Int. Ed. 56(2017) 12327-12331. doi: 10.1002/anie.201707249
20. [20]
  T. Morikawa, S. Harada, A. Nishida, J. Org. Chem. 80(2015) 8859-8867. doi: 10.1021/acs.joc.5b01393
21. [21]
  S. Zhao, G. Sirasani, S. Vaddypally, M.J. Zdilla, R.B. Andrade, Angew. Chem. Int. Ed. 52(2013) 8309-8311. doi: 10.1002/anie.201302517
22. [22]
  S.B. Jones, B. Simmons, A. Mastracchio, D.W.C. MacMillan, Nature 475(2011) 183-188. doi: 10.1038/nature10232
23. [23]
  A. Sabahi, A. Novikov, J.D. Rainier, Angew. Chem. Int. Ed. 45(2006) 4317-4320. doi: 10.1002/anie.200601278
24. [24]
  Y.L. Liu, G.S. Chen, S.J. Chen, et al., Angew. Chem. Int. Ed. 59(2020) 614-621. doi: 10.1002/anie.201911614
25. [25]
  N. Wang, S. Du, D. Li, X. Jiang, Org. Lett. 19(2017) 3167-3170. doi: 10.1021/acs.orglett.7b01292
26. [26]
  L.W. Feng, H. Ren, H. Xiong, et al., Angew. Chem. Int. Ed. 56(2017) 3055-3058. doi: 10.1002/anie.201611734
27. [27]
  J. Zhu, Y.J. Cheng, X.K. Kuang, et al., Angew. Chem. Int. Ed. 55(2016) 9224-9228. doi: 10.1002/anie.201603991
28. [28]
  X. Zhao, X. Liu, Q. Xiong, et al., Chem. Commun. 51(2015) 16076-16079. doi: 10.1039/C5CC06353A
29. [29]
  X. Zhao, X. Liu, H. Mei, et al., Angew. Chem. Int. Ed. 54(2015) 4032-4035. doi: 10.1002/anie.201410814
30. [30]
  X. Wang, S.Y. Wang, S.J. Ji, J. Org. Chem. 79(2014) 8577-8583. doi: 10.1021/jo501143m
31. [31]
  X. Wang, S.Y. Wang, S.J. Ji, Org. Lett. 15(2013) 1954-1957. doi: 10.1021/ol400606c
32. [32]
  Y.L. Liu, X.Y. Mao, X.T. Lin, G.S. Chen, Org. Chem. Front. 5(2018) 2303-2307. doi: 10.1039/C8QO00382C
33. [33]
  J.M. Saya, B. Oppelaar, R.C. Cioc, et al., Chem. Commun. 52(2016) 12482-12485. doi: 10.1039/C6CC07459F
34. [34]
  N.A. Braun, J.D. Bray, M.A. Ciufolini, Tetrahedron Lett. 40(1999) 4985-4988. doi: 10.1016/S0040-4039(99)00872-2
35. [35]
  K.C. Nicolaou, P.S. Baran, Y.L. Zhong, K. Sugita, J. Am. Chem. Soc. 124(2002) 2212-2220. doi: 10.1021/ja012124x
36. [36]
  I. Chataigner, S.R. Piettre, Org. Lett. 9(2007) 4159-4162. doi: 10.1021/ol701608b
37. [37]
  S. Beaumont, V. Pons, P. Retailleau, R.H. Dodd, P. Dauban, Angew. Chem. Int. Ed. 49(2010) 1634-1637. doi: 10.1002/anie.200906650
38. [38]
  X. Zhang, Y. Cong, G. Lin, et al., Chin. J. Org. Chem. 36(2016) 2513-2529. doi: 10.6023/cjoc201605034
39. [39]
  Y. Duan, S. Jiang, Y. Han, B. Sun, C. Zhang, Chin. J. Org. Chem. 36(2016) 1973-1984. doi: 10.6023/cjoc201605007
40. [40]
  S.V. Kohlhepp, T. Gulder, Chem. Soc. Rev. 45(2016) 6270-6288. doi: 10.1039/C6CS00361C
41. [41]
  V.V. Zhdankin, P.J. Stang, Chem. Rev. 108(2008) 5299-5358.
42. [42]
  V.V. Zhdankin, P.J. Stang, Chem. Rev. 102(2002) 2523-2584. doi: 10.1021/cr010003+
43. [43]
  P.J. Stang, V.V. Zhdankin, Chem. Rev. 96(1996) 1123-1178. doi: 10.1021/cr940424+
44. [44]
  J. Chen, H. Qu, J. Peng, C. Chen, Chin. J. Org. Chem. 35(2015) 937-946. doi: 10.6023/cjoc201501004
45. [45]
  Z. Zhang, X. Li, M. Song, et al., J. Org. Chem. 84(2019) 12792-12799. doi: 10.1021/acs.joc.9b01362
46. [46]
  Z. Zhang, D. Zheng, Y. Wan, et al., J. Org. Chem. 83(2018) 1369-1376. doi: 10.1021/acs.joc.7b02880
47. [47]
  C. Yan, J. Sun, C.G. Yan, Chin. Chem. Lett. (2020), doi: http://dx.doi.org/10.1016/j.cclet.2020.08.052. doi: 10.1016/j.cclet.2020.08.052
48. [48]
  K.K. Wang, W. Du, J. Zhu, Y.C. Chen, Chin. Chem. Lett. 28(2017) 512-516. doi: 10.1016/j.cclet.2016.11.003
49. [49]
  R.G. Shi, C.G. Yan, Chin. Chem. Lett. 27(2016) 575-578. doi: 10.1016/j.cclet.2016.02.016
50. [50]
  B. Wang, W.A. Nack, G. He, S.Y. Zhang, G. Chen, Chem. Sci. 5(2014) 3952-3957. doi: 10.1039/C4SC01545B
51. [51]
  Y. Feng, G. Chen, Angew. Chem. Int. Ed. 49(2010) 958-961. doi: 10.1002/anie.200905134
52. [52]
  P.X. Ling, S.L. Fang, X.S. Yin, et al., Chem. Commun. 53(2017) 6351-6354. doi: 10.1039/C7CC02426F
53. [53]
  K. Chen, X. Li, S.Q. Zhang, B.F. Shi, Org. Chem. Front. 3(2016) 204-208. doi: 10.1039/C5QO00319A
54. [54]
  T.T. Nguyen, O. Daugulis, Chem. Commun. 53(2017) 4609-4611. doi: 10.1039/C7CC02063E
55. [55]
  H. Wang, Z. Bai, T. Jiao, et al., J. Am. Chem. Soc. 140(2018) 3542-3546. doi: 10.1021/jacs.8b00641
56. [56]
  K.S. Yang, J.A. Gurak, Z. Liu, K.M. Engle, J. Am. Chem. Soc. 138(2016) 14705-14712. doi: 10.1021/jacs.6b08850
57. [57]
  K.C. Nicolaou, K. Sugita, P.S. Baran, Y.L. Zhong, J. Am. Chem. Soc. 124(2002) 2221-2232. doi: 10.1021/ja012125p
58. [58]
  A. Duschek, S.F. Kirsch, Angew. Chem. Int. Ed. 50(2011) 1524-1552.
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