Construction of the [6,5,7,5] Tetracyclic Core of Calyciphylline A Type Alkaloids via a Tandem Semipinacol Rearrangement/Nicholas Reaction

Organic Letters

Volumn 19, Issue 17, 2017, Pages 4648-4651

  Shao, Hui ^a   Bao, Wen ^b   Jing, Ze Ran ^b   Wang, Yun Peng ^b   Zhang, Fu Min ^b   Wang, Shao Hua ^b   Tu, Yong Qiang ^a,b  

^a SHANGHAI JIAO TONG UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85028749374     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.7b02274     Document Type: Article

References (45)

1. Wu, H.; Zhang, X.; Ding, L.; Chen, S.; Yang, J.; Xu, X. Planta Med. 2013, 79, 1589-1598 10.1055/s-0033-1351024
2. Kobayashi, J. i.; Kubota, T. Nat. Prod. Rep. 2009, 26, 936-962 10.1039/b813006j
3. Dong, M.; Zhang, M. L.; Shi, Q. W.; Gu, Y. C.; Kiyota, H. Curr. Org. Chem. 2009, 13, 646-682 10.2174/138527209787847345
4. Li, Z.-Y.; Guo, Y.-W. Chin. J. Org. Chem. 2007, 27, 565
5. Zhang, H.; Zhang, D.-D.; Li, J.-Y.; Shyaula, S. L.; Li, J.; Yue, J.-M. RSC Adv. 2016, 6, 44402-44409 10.1039/C6RA06420E
6. Zhang, H.; Shyaula, S. L.; Li, J.-Y.; Li, J.; Yue, J.-M. J. Nat. Prod. 2015, 78, 2761-2767 10.1021/acs.jnatprod.5b00741
7. Xu, J.-B.; Zhang, H.; Gan, L.-S.; Han, Y.-S.; Wainberg, M. A.; Yue, J.-M. J. Am. Chem. Soc. 2014, 136, 7631-7633 10.1021/ja503995b
8. Büschleb, M.; Dorich, S.; Hanessian, S.; Tao, D.; Schenthal, K. B.; Overman, L. E. Angew. Chem., Int. Ed. 2016, 55, 4156-4186 10.1002/anie.201507549
9. Long, R.; Huang, J.; Gong, J.; Yang, Z. Nat. Prod. Rep. 2015, 32, 1584-1601 10.1039/C5NP00046G
10. Chattopadhyay, A. K.; Hanessian, S. Chem. Rev. 2017, 117, 4104-4146 10.1021/acs.chemrev.6b00412
11. Kang, B.; Jakubec, P.; Dixon, D. J. Nat. Prod. Rep. 2014, 31, 550-562 10.1039/C3NP70115H
12. Coussanes, G.; Bonjoch, J. Org. Lett. 2017, 19, 878-881 10.1021/acs.orglett.7b00035
13. Guo, J.-J.; Li, Y.; Cheng, B.; Xu, T.; Tao, C.; Yang, X.; Zhang, D.; Yan, G.; Zhai, H. Chem.-Asian J. 2015, 10, 865-868 10.1002/asia.201403061
14. Stockdill, J. L.; Lopez, A. M.; Ibrahim, A. A. Tetrahedron Lett. 2015, 56, 3503-3506 10.1016/j.tetlet.2015.01.121
15. Ma, D.; Cheng, H.; Huang, C.; Xu, L. Tetrahedron Lett. 2015, 56, 2492-2495 10.1016/j.tetlet.2015.03.097
16. Diaba, F.; Martínez-Laporta, A.; Coussanes, G.; Fernández, I.; Bonjoch, J. Tetrahedron 2015, 71, 3642-3651 10.1016/j.tet.2014.11.044
17. Xiong, X.; Li, Y.; Lu, Z.; Wan, M.; Deng, J.; Wu, S.; Shao, H.; Li, A. Chem. Commun. 2014, 50, 5294-5297 10.1039/c3cc47873d
18. Ibrahim, A. A.; Golonka, A. N.; Lopez, A. M.; Stockdill, J. L. Org. Lett. 2014, 16, 1072-1075 10.1021/ol4034868
19. Wang, L.; Xu, C.; Chen, L.; Hao, X.; Wang, D. Z. Org. Lett. 2014, 16, 1076-1079 10.1021/ol403609c
20. Darses, B.; Michaelides, I. N.; Sladojevich, F.; Ward, J. W.; Rzepa, P. R.; Dixon, D. J. Org. Lett. 2012, 14, 1684-1687 10.1021/ol3002267
21. Yao, Y.; Liang, G. Org. Lett. 2012, 14, 5499-5501 10.1021/ol3026395
22. Yang, M.; Wang, L.; He, Z.-H.; Wang, S.-H.; Zhang, S.-Y.; Tu, Y.-Q.; Zhang, F.-M. Org. Lett. 2012, 14, 5114-5117 10.1021/ol302386g
23. Xu, C.; Wang, L.; Hao, X.; Wang, D. Z. J. Org. Chem. 2012, 77, 6307-6313 10.1021/jo300776d
24. Xu, C.; Liu, Z.; Wang, H.; Zhang, B.; Xiang, Z.; Hao, X.; Wang, D. Z. Org. Lett. 2011, 13, 1812-1815 10.1021/ol200312q
25. Sladojevich, F.; Michaelides, I. N.; Darses, B.; Ward, J. W.; Dixon, D. J. Org. Lett. 2011, 13, 5132-5135 10.1021/ol202000w
26. Solé, D.; Urbaneja, X.; Bonjoch, J. Org. Lett. 2005, 7, 5461-5464 10.1021/ol052230u
27. Wang, S.-H.; Li, B.-S.; Tu, Y.-Q. Chem. Commun. 2014, 50, 2393-2408 10.1039/C3CC48547A
28. Wang, B.; Tu, Y. Q. Acc. Chem. Res. 2011, 44, 1207-1222 10.1021/ar200082p
29. Song, Z.-L.; Fan, C.-A.; Tu, Y.-Q. Chem. Rev. 2011, 111, 7523-7556 10.1021/cr200055g
30. Green, J. Synlett 2012, 23, 1271-1282 10.1055/s-0031-1290486
31. Kann, N. Curr. Org. Chem. 2012, 16, 322-334 10.2174/138527212799499949
32. Green, J. R. Eur. J. Org. Chem. 2008, 2008, 6053-6062 10.1002/ejoc.200800836
33. Nicholas, K. M. Acc. Chem. Res. 1987, 20, 207-214 10.1021/ar00138a001
34. Teobald, B. J. Tetrahedron 2002, 58, 4133-4170 10.1016/S0040-4020(02)00315-0
35. Muller, T. J. J. Eur. J. Org. Chem. 2001, 2001, 2021-2033 10.1002/1099-0690(200106)2001:11<2021::AID-EJOC2021>3.0.CO;2-G
36. Welker, M. E. Curr. Org. Chem. 2001, 5, 785-807 10.2174/1385272013375175
37. Green, J. R. Curr. Org. Chem. 2001, 5, 809-826 10.2174/1385272013375247
38. For our previous study, see: Shao, H.; Zhang, X. M.; Wang, S. H.; Zhang, F. M.; Tu, Y. Q.; Yang, C. Chem. Commun. 2014, 50, 5691-5695 10.1039/C3CC49650C
39. Nicolaou, K. C.; Bulger, P. G.; Sarlah, D. Angew. Chem., Int. Ed. 2005, 44, 4490-4527 10.1002/anie.200500369
40. Wu, K.-M.; Okamura, W. H. J. Org. Chem. 1990, 55, 4025-4033 10.1021/jo00300a015
41. Catino, A. J.; Forslund, R. E.; Doyle, M. P. J. Am. Chem. Soc. 2004, 126, 13622-13623 10.1021/ja045330o
42. Ilardi, E. A.; Stivala, C. E.; Zakarian, A. Chem. Soc. Rev. 2009, 38, 3133-3148 10.1039/b901177n
43. Watanabe, H.; Iwamoto, M.; Nakada, M. J. Org. Chem. 2005, 70, 4652-4658 10.1021/jo050349a
44. Jacquemot, G.; Maertens, G.; Canesi, S. Chem.-Eur. J. 2015, 21, 7713-7715 10.1002/chem.201500185
45. Nagaoka, H.; Shibuya, K.; Yamada, Y. Tetrahedron 1994, 50, 661-688 10.1016/S0040-4020(01)80785-7