Asymmetric Synthesis of the Tetracyclic Skeleton of Natural Product Arborisidine

doi:10.6023/cjoc201805025

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (9): 2427-2434.DOI: 10.6023/cjoc201805025 Previous Articles Next Articles

Special Issue: 合成科学

Articles

天然产物Arborisidine四环骨架的不对称合成

陈志涛^a, 肖涛^a, 宋颢^b, 秦勇^b

a 重庆大学药学院重庆 401331;
b 四川大学华西药学院成都 610041

收稿日期:2018-05-10 修回日期:2018-06-04 发布日期:2018-06-15
通讯作者: 宋颢, 秦勇 E-mail:songhao@scu.edu.cn;yongqin@scu.edu.cn
基金资助:
国家自然科学基金（Nos.21572140，21732005）资助项目.

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

Received:2018-05-10 Revised:2018-06-04 Published:2018-06-15
Contact: 10.6023/cjoc201805025 E-mail:songhao@scu.edu.cn;yongqin@scu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21572140, 21732005).

1. Asymmetric Synthesis of the Tetracyclic Skeleton of Natural Product Arborisidine.PDF(1169KB)

Abstract

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.

Key words: indole alkaloid, arborisidine, Saegusa oxidation, aaz-Michael addition, asymmetric synthesis

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Chen Zhitao, Xiao Tao, Song Hao, Qin Yong. Asymmetric Synthesis of the Tetracyclic Skeleton of Natural Product Arborisidine[J]. Chin. J. Org. Chem., 2018, 38(9): 2427-2434.

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[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] Wong, S.-P.; Gan, C.-Y.; Lim, K.-H.; Ting, K.-N.; Low, Y.-Y.; Kam, T.-S. Org. Lett. 2015, 17, 3628.
[3] Subramaniam, G.; Hiraku, O.; Hayashi, M.; Koyano, T.; Komiyama, K.; Kam, T.-S. J. Nat. Prod. 2007, 70, 1783.
[4] Schnoes, H. K.; Biemann, K.; Mokry, J.; Kompis, L.; Chatterjee, A.; Ganguli, G. J. Org. Chem. 1966, 31, 1641.
[5] Li, L.; Yang, T.; Liu, Y.; Liu, J.; Li, M.; Wang, Y.; Yang, S.; Zou, Q.; Li, G. Org. Lett. 2012, 14, 3450.
[6] Gan, P.; Pitzen, J.; Qu, P.; Snyder, S. A. J. Am. Chem. Soc. 2018, 140, 919.
[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] (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] Moreno, J.; Picazo, E.; Morrill, L. A.; Smith, J. M.; Garg, N. K. J. Am. Chem. Soc. 2016, 138, 1162.
[10] Ren, W.; Wang, Q.; Zhu, J. Angew. Chem., Int. Ed. 2016, 55, 3500.
[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] Nishiyama, D.; Ohara, A.; Chiba, H.; Kumagai, H.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2016, 18, 1670.
[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] Smith, M. W.; Zhou, Z.; Gao, A. X.; Shimbayashi, T.; Snyder, S. A. Org. Lett. 2017, 19, 1004.
[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] Zhang, D.; Song, H.; Qin, Y. Acc. Chem. Res. 2011, 44, 447
[17] Shen, L.; Zhang, M.; Wu, Y.; Qin, Y. Angew. Chem., Int. Ed. 2008, 47, 3618.
[18] Zhang, M.; Huang, X.; Shen, L.; Qin, Y. J. Am. Chem. Soc. 2009, 131, 6013.
[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.

天然产物Arborisidine四环骨架的不对称合成

Asymmetric Synthesis of the Tetracyclic Skeleton of Natural Product Arborisidine

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