Mg(ClO 4) 2-catalyzed intramolecular allylic amination: Application to the total synthesis of demethoxyfumitremorgin C

Tetrahedron

Volumn 68, Issue 22, 2012, Pages 4225-4232

  Jiang, Danfeng ^a   Xu, Zhengren ^a   Jia, Yanxing ^a,b  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

Amination; Magnesium; Natural product; Nitrogen heterocycles; Total synthesis

Indexed keywords

ALCOHOL; ALLYL COMPOUND; ANTIFUNGAL AGENT; CARBAMIC ACID DERIVATIVE; DEMETHOXYFUMITREMORGIN C; MAGNESIUM PERCHLORATE; NITROGEN; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; DRUG SYNTHESIS; EPIMER; NUCLEOPHILICITY; PRIORITY JOURNAL; SUBSTITUTION REACTION;

EID: 84860487721     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.03.097     Document Type: Article

References (66)

1. P.M. Dewick Medicinal Natural Products - A Biosynthetic Approach 2nd ed. 2001 Wiley Chichester, UK
2. J.D. Scott, and R.M. Williams Chem. Rev. 102 2002 1669 1730
3. E.D. Cox, and J.M. Cook Chem. Rev. 95 1995 1797 1842
4. J. Royer, M. Bonin, and L. Micouin Chem. Rev. 104 2004 2311 2352
5. M. Chrzanowska, and M.D. Rozwadowska Chem. Rev. 104 2004 3341 3370 For reviews of palladium-catalyzed C-N bond formation, see
6. G. Zeni, and R.C. Larock Chem. Rev. 104 2004 2285 2309
7. G. Zeni, and R.C. Larock Chem. Rev. 106 2006 4644 4680
8. D.S. Surry, and S.L. Buchwald Chem. Sci. 2 2011 27 50
9. D.S. Surry, and S.L. Buchwald Angew. Chem., Int. Ed. 47 2008 6338 6361
10. D. Ma, and Q. Cai Acc. Chem. Res. 41 2008 1450 1460
11. M. Johannsen, and K.A. Jorgensen Chem. Rev. 98 1998 1689 1708 For recent reviews of palladium-catalyzed C-N bond formation from allylic alcohols, see
12. J. Muzart Tetrahedron 61 2005 4179 4212
13. J. Muzart Eur. J. Org. Chem. 2007 3077 3089
14. Y. Tamaru Eur. J. Org. Chem. 2005 2647 2656
15. T. Nishikata, and B.H. Lipshutz Org. Lett. 11 2009 2377 2379
16. I. Usui, S. Schmidt, M. Keller, and B. Breit Org. Lett. 10 2008 1207 1210
17. H. Kinoshita, H. Shinokubo, and K. Oshima Org. Lett. 6 2004 4085 4088
18. Y.-J. Shue, S.-C. Yang, and H.-C. Lai Tetrahedron Lett. 44 2003 1481 1485
19. F. Ozawa, H. Okamoto, S. Kawagishi, S. Yamamoto, T. Minami, and M. Yoshifuji J. Am. Chem. Soc. 124 2002 10968 10969 For Pt- or Au-catalyzed amination using simple amines or anilines as nucleophiles, see
20. T. Ohshima, Y. Miyamoto, J. Ipposhi, Y. Nakahara, M. Utsunomiya, and K. Mashima J. Am. Chem. Soc. 131 2009 14317 14328
21. M. Utsunomiya, Y. Miyamoto, J. Ipposhi, T. Ohshima, and K. Mashima Org. Lett. 9 2007 3371 3374
22. P. Mukherjee, and R.A. Widenhoefer Org. Lett. 13 2011 1334 1337 For Bronsted acids-catalyzed amination using simple amines or anilines as nucleophiles, see
23. K. Motokura, N. Nakagiri, T. Mizugaki, K. Ebitani, and K. Kaneda J. Org. Chem. 72 2007 6006 6015
24. Y. Yokoyama, H. Hikawa, M. Mitsuhashi, A. Uyama, Y. Hiroki, and Y. Murakami Eur. J. Org. Chem. 2004 1244 1253
25. Y. Yokoyama, T. Matsumoto, and Y. Murakami J. Org. Chem. 60 1995 1486 1487 For asymmetric amination, see
26. M. Roggen, and E.M. Carreira J. Am. Chem. Soc. 132 2010 11917 11919
27. C. Defieber, M.A. Ariger, P. Moriel, and E.M. Carreira Angew. Chem., Int. Ed. 46 2007 3139 3143
28. Y. Yamashita, A. Gospalarathnam, and J.F. Hartwig J. Am. Chem. Soc. 129 2007 7508 7509
29. S.M. Hande, N. Kawai, and J. Uenishi J. Org. Chem. 74 2009 244 253
30. L. Banfi, A. Basso, V. Cerulli, G. Guanti, and R. Riva J. Org. Chem. 73 2008 1608 1611
31. J.-M. Ku, B.-S. Jeong, S.-s. Jew, and H.-g. Park J. Org. Chem. 72 2007 8115 8118
32. J. Eustache, P.V. de Weghe, D. Le Nouen, H. Uyehara, C. Kabuto, and Y. Yamamoto J. Org. Chem. 70 2005 4043 4054
33. H. Yokoyama, H. Ejiri, M. Miyazawa, S. Yamaguchi, and Y. Hirai Tetrahedron: Asymmetry 18 2007 852 856
34. H. Makabe, L.K. Kong, and M. Hirota Org. Lett. 5 2003 27 29
35. H. Yokoyama, K. Otaya, H. Kobayashi, M. Miyazawa, S. Yamaguchi, and Y. Hirai Org. Lett. 2 2000 2427 2429
36. H. Yokoyama, K. Otaya, S. Yamaguchi, and Y. Hirai Tetrahedron Lett. 39 1998 5971 5974
37. P.J. Harrington, L.S. Hegedus, and K.F. McDaniel J. Am. Chem. Soc. 109 1987 4335 4338
38. C.-W. Chien, C. Shi, C.-F. Lin, and I. Ojima Tetrahedron 67 2011 6513 6523
39. C. Shi, and I. Ojima Tetrahedron 63 2007 8563 8570
40. P. Kothandaraman, S.J. Foo, and P.W.H. Chan J. Org. Chem. 74 2009 5947 5952
41. S. Guo, F. Song, and Y. Liu Synlett 2007 964 968
42. A. Guérinot, A. Serra-Muns, C. Gnamm, C. Bensoussan, S. Reymond, and J. Cossy Org. Lett. 12 2010 1808 1811
43. U. Jana, S. Maiti, and S. Biswas Tetrahedron Lett. 49 2008 858 862
44. N. Kawai, M. Matsuda, and J. Uenishi Tetrahedron 67 2011 8648 8653
45. N. Kawai, R. Abe, M. Matsuda, and J. Uenishi J. Org. Chem. 76 2011 2102 2114
46. N. Kawai, R. Abe, and J. Uenishi Tetrahedron Lett. 50 2009 6580 6583
47. H.B. Qin, N. Yamagiwa, S. Matsunaga, and M. Shibasaki Angew. Chem., Int. Ed. 46 2007 409 413
48. H. Yang, L. Fang, M. Zhang, and C. Zhu Eur. J. Org. Chem. 2009 666 672
49. H. Yamamoto, E. Ho, K. Namba, H. Imagawa, and M. Nishizawa Chem. - Eur. J. 16 2010 11271 11274
50. W. Wu, W. Rao, Y.Q. Er, J.K. Loh, C.Y. Poh, and P.W.H. Chan Tetrahedron Lett. 49 2008 2620 2624
51. K. Motokura, N. Nakagiri, K. Mori, T. Mizugaki, K. Ebitani, K. Jitsukawa, and K. Kaneda Org. Lett. 8 2006 4617 4620
52. S. Shirakawa, and S. Shimizu Synlett 2008 1539 1542
53. G.-W. Wang, Y.-B. Shen, and X.-L. Wu Eur. J. Org. Chem. 2008 4367 4371
54. Z. Xu, Q. Li, L. Zhang, and Y. Jia J. Org. Chem. 74 2009 6859 6862
55. Z. Xu, W. Hu, Q. Liu, L. Zhang, and Y. Jia J. Org. Chem. 75 2010 7626 7635
56. J.N. Hernández, M.A. Ramírez, M.L. Rodríguez, and V.S. Martín Org. Lett. 10 2008 2349 2352
57. C.-B. Cui, H. Kakeya, and H. Osada J. Antibiot. 49 1996 534 540
58. R. Plate, P. Hermkens, H. Behm, and H. Ottenheijm J. Org. Chem. 52 1987 560 564
59. R. Plate, P. Hermkens, and H. Ottenheijm Tetrahedron 44 1988 1991 2000
60. S. Kotato, M. Nakagawa, M. Hongu, T. Kawate, and T. Hino Tetrahedron 44 1988 359 377
61. P. Bailey, S. Hollinshead, and N. Mclay Tetrahedron Lett. 30 1989 6421 6422
62. P. Bailey, P. Cochrane, K. Lorenz, I. Collier, D. Pearson, and G. Rosair Tetrahedron Lett. 42 2001 113 115
63. P.D. Bailey, S.P. Hollinshead, N.R. McLay, J.H. Everett, C.D. Reynolds, S.D. Wood, and F. Giordano J. Chem. Soc., Perkin Trans. 1 1993 451 458
64. H. Wang, and A. Ganesan Tetrahedron Lett. 38 1997 4327 4328
65. H. Wang, and A. Ganesan Org. Lett. 1 1999 1647 1649
66. A. Coste, M. Toumi, K. Wright, V. Razafimahaléo, F. Couty, J. Marrot, and G. Evano Org. Lett. 10 2008 3841 3844