Protecting-group-free total synthesis of (-)-rhazinilam and (-)-rhazinicine using a gold-catalyzed cascade cyclization

Angewandte Chemie - International Edition

Volumn 52, Issue 28, 2013, Pages 7168-7171

  Sugimoto, Kenji ^a   Toyoshima, Kazuki ^a   Nonaka, Shiori ^a   Kotaki, Kenta ^a   Ueda, Hirofumi ^a   Tokuyama, Hidetoshi ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

alkaloids; cyclization; gold; natural products; total synthesis

Indexed keywords

ASYMMETRIC TOTAL SYNTHESIS; CASCADE CYCLIZATION; CASCADE REACTIONS; INDOLIZINONES; NATURAL PRODUCTS; TOTAL SYNTHESIS;

ALKALOIDS; CATALYSIS; GOLD; SYNTHESIS (CHEMICAL);

CYCLIZATION;

ALKALOID; FUSED HETEROCYCLIC RINGS; GOLD; INDOLIZINE DERIVATIVE; LACTAM; RHAZINICINE; RHAZINILAM;

APOCYNACEAE; ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; NATURAL PRODUCTS; STEREOISOMERISM; SYNTHESIS; TOTAL SYNTHESIS;

ALKALOIDS; CYCLIZATION; GOLD; NATURAL PRODUCTS; TOTAL SYNTHESIS;

ALKALOIDS; APOCYNACEAE; CATALYSIS; CYCLIZATION; GOLD; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; INDOLIZINES; LACTAMS; STEREOISOMERISM;

EID: 84880143408     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201303067     Document Type: Article

References (53)

1. O. Baudoin, D. Guénard, F. Guéritte, Mini-Rev. Org. Chem. 2004, 1, 333-341, and references therein.
2. H. H. A. Linde, Helv. Chim. Acta 1965, 48, 1822-1842
3. D. J. Abraham, R. D. Rosenstein, R. L. Lyon, H. H. S. Fong, Tetrahedron Lett. 1972, 13, 909-912.
4. I. Gerasimenko, Y. Sheludko, J. Stöckigt, J. Nat. Prod. 2001, 64, 114-116
5. T. S. Kam, G. Subramaniam, W. Chen, Phytochemistry 1999, 51, 159-169.
6. B. David, T. Sévenet, M. Morgat, D. Guénard, A. Moisand, Y. Tollon, O. Thoison, M. Wright, Cell Motil. Cytoskeleton 1994, 28, 317-326.
7. A. H. Ratcliffe, G. F. Smith, G. N. Smith, Tetrahedron Lett. 1973, 14, 5179-5184
8. J. A. Johnson, D. Sames, J. Am. Chem. Soc. 2000, 122, 6321-6322
9. P. Magnus, T. Rainey, Tetrahedron 2001, 57, 8647-8651
10. A. L. Bowie, Jr., C. C. Hughes, D. Trauner, Org. Lett. 2005, 7, 5207-5209. For syntheses of (-)-rhazinilam, see
11. J. A. Johnson, N. Li, D. Sames, J. Am. Chem. Soc. 2002, 124, 6900-6903
12. Z. Liu, A. S. Wasmuth, S. G. Nelson, J. Am. Chem. Soc. 2006, 128, 10352-10353
13. M. G. Banwell, D. A. S. Beck, A. C. Willis, ARKIVOC 2006, 163-174
14. Z. Gu, A. Zakarian, Org. Lett. 2010, 12, 4224-4227. For synthesis of (±)-rhazinicine, see
15. E. M. Beck, R. Hatley, M. J. Gaunt, Angew. Chem. 2008, 120, 3046-3049
16. Angew. Chem. Int. Ed. 2008, 47, 3004-3007
17. L. McMurray, E. M. Beck, M. J. Gaunt, Angew. Chem. 2012, 124, 9422-9425
18. Angew. Chem. Int. Ed. 2012, 51, 9288-9291.
19. A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211
20. D. J. Gorin, F. D. Toste, Nature 2007, 446, 395-403
21. Z. Li, C. Brouwer, C. He, Chem. Rev. 2008, 108, 3239-3265
22. A. Arcadi, Chem. Rev. 2008, 108, 3266-3325
23. E. Jiménez-Núñez, A. M. Echavarren, Chem. Rev. 2008, 108, 3326-3350
24. D. J. Gorin, B. D. Sherry, F. D. Toste, Chem. Rev. 2008, 108, 3351-3378
25. A. S. K. Hashmi, Angew. Chem. 2010, 122, 5360-5369
26. Angew. Chem. Int. Ed. 2010, 49, 5232-5241.
27. R. A. Widenhoefer, X. Han, Eur. J. Org. Chem. 2006, 4555-4563
28. T. E. Müller, K. C. Hultzsch, M. Yus, F. Foubelo, M. Tada, Chem. Rev. 2008, 108, 3795-3892.
29. S. Obika, Y. Yasui, R. Yamada, Y. Takemoto, J. Org. Chem. 2008, 73, 5206-5209
30. G. Verniest, A. Padwa, Org. Lett. 2008, 10, 4379-4382
31. T. Enomoto, A.-L. Girard, Y. Yasui, Y. Takemoto, J. Org. Chem. 2009, 74, 9158-9164.
32. D. J. Gorin, N. R. Davis, F. D. Toste, J. Am. Chem. Soc. 2005, 127, 11260-11261
33. T. J. Harrison, J. A. Kozak, M. Corbella-Pané, G. R. Dake, J. Org. Chem. 2006, 71, 4525-4529
34. M. Egi, K. Azechi, S. Akai, Org. Lett. 2009, 11, 5002-5005
35. A. Aponick, C.-Y. Li, J. Malinge, E. F. Marques, Org. Lett. 2009, 11, 4624-4627
36. A. Saito, T. Konishi, Y. Hanzawa, Org. Lett. 2010, 12, 372-374.
37. K. Sonogashira, Y. Tohda, N. Hagiwara, Tetrahedron Lett. 1975, 16, 4467-4470.
38. J. H. Teles, S. Brode, M. Chabanas, Angew. Chem. 1998, 110, 1475-1478
39. Angew. Chem. Int. Ed. 1998, 37, 1415-1418.
40. N. Mézailles, L. Ricard, F. Gagosz, Org. Lett. 2005, 7, 4133-4136.
41. C. Nieto-Oberhuder, S. Lõpez, A. M. Echavarren, J. Am. Chem. Soc. 2005, 127, 6178-6179.
42. A substrate bearing ortho-nitro phenyl group did not provide the desired product possibly because of participation of the nitro group to the activated C-C triple bond:, N. Asao, K. Sato, Y. Yamamoto, Tetrahedron Lett. 2003, 44, 5675-5677.
43. J. d'Angelo, D. Desmaële, F. Dumas, A. Guingant, Tetrahedron: Asymmetry 1992, 3, 459-505.
44. G. A. Macalpine, J. Warkentin, Can. J. Chem. 1978, 56, 308-315.
45. Preparation of this aldehyde by the same strategy, see:, R. Nakajima, T. Ogino, S. Yokoshima, T. Fukuyama, J. Am. Chem. Soc. 2010, 132, 1236-1237.
46. G. A. Kraus, M. J. Taschner, J. Org. Chem. 1980, 45, 1175-1176
47. B. S. Bal, W. E. Childers, Jr., H. W. Pinnick, Tetrahedron 1981, 37, 2091-2096.
48. High reactivity of N-acyl pyrroles toward nucleophiles, see:, D. A. Evans, G. Borg, K. A. Scheidt, Angew. Chem. 2002, 114, 3320-3323
49. Angew. Chem. Int. Ed. 2002, 41, 3188-3191.
50. J. T. Markiewicz, O. Wiest, P. Helquist, J. Org. Chem. 2010, 75, 4887-4890.
51. G. Olah, S. C. Narang, B. G. B. Gupta, R. Malhotra, J. Org. Chem. 1979, 44, 1247-1251.
52. D. P. Phillips, X.-F. Zhu, T. L. Lau, X. He, K. Yang, H. Liu, Tetrahedron Lett. 2009, 50, 7293-7296.
53. I. S. Young, P. S. Baran, Nat. Chem. 2009, 1, 193-205.