Citation: Chen Zhitao, Xiao Tao, Song Hao, Qin Yong. Asymmetric Synthesis of the Tetracyclic Skeleton of Natural Product Arborisidine[J]. Chinese Journal of Organic Chemistry, ;2018, 38(9): 2427-2434. doi: 10.6023/cjoc201805025 shu

Asymmetric Synthesis of the Tetracyclic Skeleton of Natural Product Arborisidine

Chen Zhitao ^a ,
Xiao Tao ^a ,
Song Hao ^b,, ,
Qin Yong ^b,,

a.
School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331
b.
West China School of Pharmacy, Sichuan University, Chengdu 610041

Corresponding author: Song Hao, songhao@scu.edu.cn Qin Yong, yongqin@scu.edu.cn
Received Date: 10 May 2018
Revised Date: 4 June 2018
Available Online: 15 September 2018
Fund Project: the National Natural Science Foundation of China 21732005Project supported by the National Natural Science Foundation of China (Nos. 21572140, 21732005)the National Natural Science Foundation of China 21572140

Figures(5)

Asymmetric synthesis of the tetracyclic skeleton of arborisidine is reported. Starting from the enantiomerically pure compound 10, 9-di-tert-butyl5-ethyl(4S, 8R)-6-hydroxy-7, 8-dihydro-9H-8a, 4b-(epiminoethano)carbazole-5, 9, 10-tricar-boxylate (11) which was reported earlier by our group, a Krapcho decarboxylation reaction was used to afford the ketone, and then a reductive ring-opening method was applied to open the pyrrolidine ring of the substrate. The C(15)-C(16) double bond and the methyl group at C(16) of A/B/D tricyclic skeleton were introduced via Saegusa oxidation and Michael reaction, respectively. Finally, an intramolecular aza-Michael addition reaction was used as a key reaction to construct the C-ring and C(16) quaternary center, which led to the efficiently asymmetric synthesis of A/B/C/D tetracyclic skeleton of arborisidine.
- indole alkaloid,
- arborisidine,
- Saegusa oxidation,
- aaz-Michael addition,
- asymmetric synthesis
1. [1]
  Wong, S.-P.; Chong, K.-W.; Lim, K.-H.; Lim, S.-H.; Low, Y.-Y.; Kam, T.-S. Org. Lett. 2016, 18, 1618.
2. [2]
  Wong, S.-P.; Gan, C.-Y.; Lim, K.-H.; Ting, K.-N.; Low, Y.-Y.; Kam, T.-S. Org. Lett. 2015, 17, 3628. doi: 10.1021/acs.orglett.5b01757
3. [3]
  Subramaniam, G.; Hiraku, O.; Hayashi, M.; Koyano, T.; Komiyama, K.; Kam, T.-S. J. Nat. Prod. 2007, 70, 1783. doi: 10.1021/np0703747
4. [4]
  Schnoes, H. K.; Biemann, K.; Mokry, J.; Kompis, L.; Chatterjee, A.; Ganguli, G. J. Org. Chem. 1966, 31, 1641. doi: 10.1021/jo01343a507
5. [5]
  Li, L.; Yang, T.; Liu, Y.; Liu, J.; Li, M.; Wang, Y.; Yang, S.; Zou, Q.; Li, G. Org. Lett. 2012, 14, 3450. doi: 10.1021/ol301400e
6. [6]
  Gan, P.; Pitzen, J.; Qu, P.; Snyder, S. A. J. Am. Chem. Soc. 2018, 140, 919. doi: 10.1021/jacs.7b07724
7. [7]
  (a) Zu, L.; Boal, B. W.; Garg, N. K. J. Am. Chem. Soc. 2011, 133, 8877.
  (b) Ren, W.; Wang, Q.; Zhu, J. Angew. Chem., Int. Ed. 2014, 53, 1818.
  (c) Teng, M.; Zi, W.; Ma, D. Angew. Chem., Int. Ed. 2014, 53, 1814.
8. [8]
  (a) Moreno, J.; Picazo, E.; Morrill, L. A.; Smith, J. M.; Garg, N. K. J. Am. Chem. Soc. 2016, 138, 1162.
  (b) Jiang, S.-Z.; Zeng, X.-Y.; Liang, X.; Lei, T.; Wei, K.; Yang, Y.-R. Angew. Chem., Int. Ed. 2016, 55, 4044.
  (c) Wang, T.; Duan, X.; Zhao, H.; Zhai, S.; Tao, C.; Wang, H.; Li, Y.; Cheng, B.; Zhai, H. Org. Lett. 2017, 19, 1650.
9. [9]
  Moreno, J.; Picazo, E.; Morrill, L. A.; Smith, J. M.; Garg, N. K. J. Am. Chem. Soc. 2016, 138, 1162. doi: 10.1021/jacs.5b12880
10. [10]
  Ren, W.; Wang, Q.; Zhu, J. Angew. Chem., Int. Ed. 2016, 55, 3500. doi: 10.1002/anie.201511638
11. [11]
  (a) Xie, X.; Wei, B.; Li, G.; Zu, L. Org. Lett. 2017, 19, 5430.
  (b) Li, G.; Xie, X.; Zu, L. Angew. Chem., Int. Ed. 2016, 55, 10483.
12. [12]
  Nishiyama, D.; Ohara, A.; Chiba, H.; Kumagai, H.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2016, 18, 1670. doi: 10.1021/acs.orglett.6b00536
13. [13]
  (a) Eckermann, R.; Breunig, M.; Gaich, T. Chem. Commun. 2016, 52, 11363.
  (b) Eckermann, R.; Breunig, M.; Gaich, T. Chem.-Eur. J. 2017, 23, 3938.
14. [14]
  Smith, M. W.; Zhou, Z.; Gao, A. X.; Shimbayashi, T.; Snyder, S. A. Org. Lett. 2017, 19, 1004. doi: 10.1021/acs.orglett.6b03839
15. [15]
  (a) Xiao, T.; Chen, Z.-T.; Deng, L.-F.; Zhang, D.; Liu, X.-Y.; Song, H.; Qin, Y. Chem. Commun. 2017, 53, 12665.
  (b) Chen, Z.-T.; Xiao, T.; Tang, P.; Zhang, D.; Qin, Y. Tetrahedron 2018, 74, 1129.
16. [16]
  Zhang, D.; Song, H.; Qin, Y. Acc. Chem. Res. 2011, 44, 447 doi: 10.1021/ar200004w
17. [17]
  Shen, L.; Zhang, M.; Wu, Y.; Qin, Y. Angew. Chem., Int. Ed. 2008, 47, 3618.
18. [18]
  Zhang, M.; Huang, X.; Shen, L.; Qin, Y. J. Am. Chem. Soc. 2009, 131, 6013. doi: 10.1021/ja901219v
19. [19]
  (a) Eckermann, R.; Gaich, T. Synthesis 2013, 45, 2813.
  (b) Smith, J. M.; Moreno, J.; Boal, B. W.; Garg, N. K. Angew. Chem., Int. Ed. 2015, 54, 400.
  (c) Adams, G, L; Smith, A. B. The Alkaloids. Chemistry and Biology, Elsevier, New York, 2016, 76, 171.
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