Synthesis of the azatricyclic ACD ring system of calyciphylline A-type Daphniphyllum alkaloids via a nonstabilized azomethine ylide generated by desilylation

Tetrahedron Letters

Volumn 56, Issue 19, 2015, Pages 2492-2495

  Ma, Ding ^a   Cheng, Hang ^a   Huang, Chunmei ^a   Xu, Liang ^a  

^a SICHUAN UNIVERSITY   (China)

Author keywords

A type alkaloids; ACD ring system 3+2 cycloaddition; Calyciphylline; Desilylation; Nonstabilized azomethine ylide

Indexed keywords

EID: 84937764017     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.03.097     Document Type: Article

References (52)

1. J. Kobayashi, and T. Kubota Nat. Prod. Rep. 26 2009 936 962
2. S.-P. Yang, and J.-M. Yue Acta Pharmacol. Sin. 33 2012 1147 1158
3. H. Morita, and J. Kobayashi Org. Lett. 5 2003 2895 2898
4. For recent isolations see: C.-S. Li, Y.-T. Di, Q. Zhang, Y. Zhang, C.-J. Tan, and X.-J. Hao Helv. Chim. Acta 92 2009 653 659
5. Y. Zhang, Y. Di, H. He, S. Li, Y. Lu, N. Gong, and X. Hao Eur. J. Org. Chem. 2011 2011 4103 4107
6. C.-R. Zhang, C.-Q. Fan, S.-H. Dong, H.-B. Liu, W.-B. Zhou, Y. Wu, and J.-M. Yue Org. Lett. 13 2011 2440 2443
7. T.-Q. Yang, Y.-T. Di, H.-P. He, Q. Zhang, Y. Zhang, and X.-J. Hao Helv. Chim. Acta 94 2011 397 403
8. T. He, Y. Zhou, Y.-H. Wang, S.-Z. Mu, and X.-J. Hao Helv. Chim. Acta 94 2011 1019 1023
9. Q.-Y. Zhang, T.-Q. Zhang, Y.-T. Yang, Y.-T. Di, and X.-J. Hao RSC Adv. 3 2013 9658 9661
10. For recent synthetic approaches to calyciphylline A-type alkaloids, see: D. Solé, X. Urbaneja, and J. Bonjoch Org. Lett. 7 2005 5461 5464
11. S. Ikeda, M. Shibuya, N. Kanoh, and Y. Iwabuchi Org. Lett. 11 2009 1833 1836
12. C. Xu, Z. Liu, H. Wang, B. Zhang, Z. Xiang, X. Hao, and D.-Z. Wang Org. Lett. 13 2011 1812 1815
13. F. Sladojevich, I.N. Michaelides, B. Darses, J.W. Ward, and D.J. Dixon Org. Lett. 13 2011 5132 5135
14. B. Darses, I.N. Michaelides, F. Sladojevich, J.W. Ward, P.R. Rzepa, and D.J. Dixon Org. Lett. 14 2012 1684 1687
15. C. Xu, L. Wang, X. Hao, and D.Z. Wang J. Org. Chem. 77 2012 6307 6313
16. B. Feng, H. Zheng, C. Zhao, P. Jing, H. Li, X. Xie, and X. She J. Org. Chem. 77 2012 8367 8373
17. M. Yang, L. Wang, Z.-H. He, S.-H. Wang, S.-Y. Zhang, Y.-Q. Tu, and F.-M. Zhang Org. Lett. 14 2012 5114 5117
18. H.-L. Li, J.-Y. Zheng, S.-A. Xu, D.-H. Ma, C.-G. Zhao, B. Fang, X.-A. Xie, and X.-G. She Chem. Asian J. 7 2012 2519 2522
19. Y.-M. Yao, and G.-X. Liang Org. Lett. 14 2012 5499 5501
20. L. Wang, C. Xu, L. Chen, X. Hao, and D.-Z. Wang Org. Lett. 16 2014 1076 1079
21. A.A. Ibrahim, A.N. Golonka, A.M. Lopez, and J.L. Stockdill Org. Lett. 16 2014 1072 1075
22. X.-C. Xiong, Y. Li, Z.-Y. Lu, M. Wan, J. Deng, S.-H. Wu, H.-W. Shao, and A. Li Chem. Commun. 2014 5294 5297
23. For a review, see: B. Kang, P. Jakubec, and D.J. Dixon Nat. Prod. Rep. 31 2014 550 562
24. For a total synthesis of one special member of calyciphylline A-type alkaloid, daphenylline with a unique arene-containing structure, see: Z. Lu, Y. Li, J. Deng, and A. Li Nat. Chem. 5 2013 679 684
25. For synthetic efforts toward Daphniphyllum alkaloids using [3+2] cycloaddition strategies, see: S.E. Denmark, and R.Y. Baiazitov J. Org. Chem. 71 2006 593 605
26. S.E. Denmark, R.Y. Baiazitov, and S.T. Nguyen Tetrahedron 65 2009 6535 6548
27. I. Coldham, A.J.M. Burrel, H.D.S. Guerrand, and N. Oram Org. Lett. 13 2011 1267 1269
28. I. Coldham, L. Watson, H. Adams, and N.G. Martin J. Org. Chem. 76 2011 2360 2366
29. G. Belanger, J. Boudreault, and F. Levesque Org. Lett. 13 2011 6204 6207
30. B.M. Trost, A.C. Gutierrez, and E.M. Ferreira J. Am. Chem. Soc. 132 2010 9206 9218
31. I. Kuwajima, and H. Urabe Org. Synth. 66 1988 87 92
32. For examples, see: T. Nagai, K. Ogawa, M. Morita, M. Koyama, A. Ando, T. Miki, and I. Kumadaki Chem. Pharm. Bull. 37 1989 1750 1755
33. J.-Q. Yu, and E.J. Corey Org. Lett. 4 2002 2727 2730
34. T.K.M. Shing, Y.-Y. Yeung, and P.L. Su Org. Lett. 8 2006 3149 3151
35. G. Pandey, K.N. Tiwari, and V.G. Puranik Org. Lett. 10 2008 3611 3614
36. E.C. McLaughlin, H. Choi, K. Wang, G. Chiou, and M.P. Doyle J. Org. Chem. 74 2009 730 738
37. R. Martin, A.W. Schmidt, G. Theumer, T. Krause, E.V. Entchev, T.V. Kurzchalia, and H.-J. Knölker Org. Biomol. Chem. 7 2009 909 920
38. N. Chidambaram, and S. Chandrasekaran J. Org. Chem. 52 1987 5048 5051
39. J.-Q. Yu, and E.J. Corey J. Am. Chem. Soc. 125 2003 3232 3233
40. A.M. Zaed, M.D. Swift, and A. Sutherland Org. Biomol. Chem. 7 2009 2678 2680
41. W.G. Salmond, M.A. Barta, and J.L. Havens J. Org. Chem. 43 1978 2057
42. The report of intramolecular [3+2] cycloaddition of azomethine ylide employing enolizable aldehyde was scarce. For a review of detailed discussion for this subject, see: I. Coldham, and R. Hufton Chem. Rev. 105 2005 2765 2809
43. W.H. Pearson, P. Stoy, and Y. Mi J. Org. Chem. 69 2004 1919 1939
44. For examples of intramolecular cycloaddition of the azomethine ylides derived from α-amino acids, see: S. Kanemasa, K. Doi, and E. Wada Bull. Chem. Soc. Jpn. 63 1990 2866 2871
45. A.G.P.R. Figueiredo, A.C. Tomé, and A.M.S. Silva Tetrahedron 63 2007 910 917
46. C. Draghici, Q. Huang, and M. Brewer J. Org. Chem. 74 2009 8410 8413
47. A.J.M. Burrell, I. Coldham, and N. Oram Org. Lett. 11 2009 1515 1518
48. I. Coldham, A.J.M. Burrell, H.D.S. Guerrand, and N. Oram Org. Lett. 13 2011 1267 1269
49. I. Coldham, A.J.M. Burrell, L.E. White, H. Adams, and N. Oram Angew. Chem., Int. Ed. 46 2007 6159 6162
50. E. Vedejs, and F.G. West Chem. Rev. 86 1986 941 955
51. S. Torii, H. Okumoto, and A. Genba Chem. Lett. 1996 747 748
52. A. Padwa, and W. Dent J. Org. Chem. 52 1987 235 244