A simple enantioselective route to functionalized indolizidines: Synthesis of (+)-ipalbidine and (+)-antofine

European Journal of Organic Chemistry

Volumn , Issue 12, 2011, Pages 2235-2238

  Pansare, Sunil V ^a   Lingampally, Rajinikanth ^a   Dyapa, Rajendar ^a  

^a MEMORIAL UNIVERSITY OF NEWFOUNDLAND   (Canada)

Author keywords

Alkaloids; Antofine; Ipalbidine; Michael addition; Organocatalysis

Indexed keywords

EID: 79953680223     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201100125     Document Type: Article

References (85)

1. J. P. Michael, Nat. Prod. Rep. 2008, 25, 139, and previous reviews on indolizidine and quinolizidine alkaloids in the series
2. J. W. Daly, T. F. Spande, H. M. Garraffo, J. Nat. Prod. 2005, 68,1556.
3. N. Asano, R. J. Nash, R. J. Molyneux, G. W. J. Fleet, Tetrahedron: Asymmetry 2000, 11, 1645.
4. Iminosugars as Glycosidase Inhibitors (Ed.:, A. E. Stütz), Wiley-VCH, Weinheim, Germany, 1999.
5. A. A. Watson, G. W. J. Fleet, N. Asano, R. J. Molyneux, R. J. Nash, Phytochemistry 2001, 56, 265.
6. C.-H. Wong, R. L. Halcomb, Y. Ichibaka, T. Kajimoto, Angew. Chem. 1995, 107, 569.
7. P. Compain, O. R. Martin, Curr. Top. Med. Chem. 2003, 3, 541.
8. S. R. Chemler, Curr. Bioact. Compd. 2009, 5, 2.
9. J. Cluzeau, W. D. Lubell, J. Org. Chem. 2004, 69, 1504.
10. For reviews on phenanthro-indolizidine alkaloids, see
11. Z. Li, Z. Jin, R. Huang, Synthesis 2001, 2365.
12. I. Bick, C. Ralph, W. Sinchai, Alkaloids 1981, 19, 193.
13. T. R. Govindachari, N. Vishwanathan, Heterocycles 1978, 11, 587. For selected recent reports, see
14. M. G. Banwell, M. O. Sydnes, Aust. J. Chem. 2004, 57, 537.
15. V. M. Sharma, K. V. Adi Seshu, C. V. Krishna, P. Prasanna, V. C. Shekhar, A. Venkateswarlu, S. Rajagopal, R. Ajaykumar, D. S. Deevi, N. V. S. R. Mamidi, R. Rajagopalan, Bioorg. Med. Chem. Lett. 2003, 13, 1679.
16. W. Zhu, G. Cai, D. Ma, Org. Lett. 2005, 7, 5545.
17. R. T. Yu, T. Rovis, J. Am. Chem. Soc. 2006, 128, 2782.
18. A. Boto, L. De, G. Yolanda, A. Juan, R. Hernandez, Eur. J. Org. Chem. 2005, 3461.
19. For reviews, see
20. A. Brandi, F. Cardona, S. Cicchi, F. M. Cordero, A. Goti, Chem. Eur. J. 2009, 15, 7808.
21. S. Perreault, T. Rovis, Chem. Soc. Rev. 2009, 38, 3149.
22. B. B. Toure, D. G. Hall, Chem. Rev. 2009, 109, 4439.
23. for a thematic series on indolizidines and quinolizidines, see: Beilstein, J. Org. Chem. 2007, 3, no. 27.
24. C. W. Jefford, Curr. Org. Chem. 2000, 4, 205.
25. S. Rajeswari, S. Chandrasekharan, T. R. Govindachari, Heterocycles 1987, 25, 659. Selected recent reports
26. A. Iza, L. Carrillo, J. L. Vicario, D. Badia, E. Reyes, J. Martinez, Org. Biomol. Chem. 2010, 8, 2238.
27. N. Sirisha, R. Raghunathan, Tetrahedron Lett. 2010, 51, 2515.
28. D. Yang, G. C. Micalizio, J. Am. Chem. Soc. 2009, 131, 17548.
29. R. Affani, S. Comesse, A. Daich, L. Hamon, C. Kadouri-Puchot, Heterocycles 2009, 78, 2193.
30. G. Barbe, G. Pelletier, A. B. Charette, Org. Lett. 2009, 11, 3398.
31. M. Katoh, H. Mizutani, T. Honda, Heterocycles 2006, 69, 193.
32. For a synthesis of (+)-ipalbidine, see
33. T. Honda, H. Namiki, H. Nagase, H. Mizutani, Tetrahedron Lett. 2003, 44, 3035.
34. L. Zhujin, L. Renrong, C. Qi, H. Hai, Acta Chim. Sinica 1985, 43, 992.
35. M. J. Niphakis, G. I. Georg, J. Org. Chem. 2010, 75, 6019. Selected syntheses of racemic ipalbidine
36. T. R. Govindachari, A. R. Sidhaye, N. Viswanathan, Tetrahedron 1970, 26, 3829.
37. H. Iida, Y. Watanabe, C. Kibayashi, J. Chem. Soc. Perkin Trans. 1 1985, 261.
38. C. W. Jefford, T. Kubota, A. Zeslona, Helv. Chim. Acta 1986, 69, 2048.
39. J. Zhou, G. Zhao, W. Jin, W. Zheng, Z. Chi, Chin. Acad. Sci., Shanghai 1988, 9, 107.
40. X. Chen, Y. Chu, Zhongguo Yaolixue Tongbao 1998, 14, 243.
41. For synthesis of (+)-antofine, see
42. [8c]
43. Z. Wang, Z. Li, K. Wang, Q. Wang, Eur. J. Org. Chem. 2010, 2, 292.
44. L. Faber, W. Wiegrebe, Helv. Chim. Acta 1973, 56, 2882. For synthesis of (-)-antofine, see
45. M. Cui, H. Song, A. Feng, Z. Wang, Q. Wang, J. Org. Chem. 2010, 75, 7018.
46. X. Yang, Q. Shi, K. F. Bastow, K.-H. Lee, Org. Lett. 2010, 12, 1416.
47. A. Fuerstner, J. W. Kennedy, Chem. Eur. J. 2006, 12, 7398.
48. S. Kim, T. Lee, E. Lee, J. Lee, G.-J. Fan, S. K. Lee, D. Kim, J. Org. Chem. 2004, 69, 3144.
49. S. Kim, J. Lee, T. Lee, H.-G. Park, D. Kim, Org. Lett. 2003, 5, 2703. For selected syntheses of racemic antofine, see
50. L. M. Ambrosini, T. A. Cernak, T. H. Lambert, Tetrahedron 2010, 66, 4882.
51. K.-L. Wang, M.-Y. Lue, Q.-M. Wang, R.-Q. Huang, Tetrahedron 2008, 64, 7504.
52. C.-R. Su, A. G. Damu, P.-C. Chiang, K. F. Bastow, S. L. Morris-Natschke, K.-H. Lee, T.-S. Wu, Bioorg. Med. Chem. 2008, 16, 6233.
53. S. Kim, Y. M. Lee, J. Lee, T. Lee, Y. Fu, Y. Song, J. Cho, D. Kim, J. Org. Chem. 2007, 72, 4886.
54. A. Camacho-Davila, J. W. Herndon, J. Org. Chem. 2006, 71, 6682.
55. S. Yamashita, N. Kurono, H. Senboku, M. Tokuda, K. Orito, Eur. J. Org. Chem. 2009, 8, 1173.
56. H.-Y. Min, H.-J. Chung, E.-H. Kim, S. Kim, E.-J. Park, S. K. Lee, Biochem. Pharmacol. 2010, 80, 1356.
57. W. Gao, A. P. C. Chen, C. H. Leung, E. A. Gullen, A. Fürstner, Q. Shi, L. Wei, K. H. Lee, Y. C. Cheng, Bioorg. Med. Chem. Lett. 2008, 18, 704.
58. K. Wang, B. Su, Z. Wang, M. Wu, Z. Li, Y. Hu, Z. Fan, N. Mi, Q. Wang, J. Agric. Food Chem. 2010, 58, 2703.
59. S. V. Pansare, K. Pandya, J. Am. Chem. Soc. 2006, 128, 9624.
60. S. V. Pansare, R. L. Kirby, Tetrahedron 2009, 65, 4557.
61. For reviews, see
62. H. Kotsuki, H. Ikishima, A. Okuyama, Heterocycles 2008, 75, 757.
63. S. Sulzer-Mosse, A. Alexakis, Chem. Commun. 2007, 30, 3123.
64. D. Enders, A. Seki, Eur. J. Org. Chem. 2002, 1877.
65. For a review on enamine catalysis, see:, S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471. For selected recent reports, see
66. B. Ni, Q. Zhang, K. Dhungana, A. D. Headley, Org. Lett. 2009, 11, 1041.
67. T. Mandal, C.-G. Zhao, Angew. Chem. 2008, 120, 7828
68. Angew. Chem. Int. Ed. 2008, 47, 7714.
69. D. Almasi, D. A. Alonso, E. Gomez-Benoga, Y. Nagel, C. Najera, Eur. J. Org. Chem. 2007, 2328.
70. For reports on the application of organocatalytic Michael addition products in total synthesis, see
71. S. Zhu, S. Yu, Y. Wang, D. Ma, Angew. Chem. Int. Ed. 2010, 49, 4656.
72. H. Ishikawa, T. Suzuki, Y. Hayashi, Angew. Chem. 2009, 121, 1330
73. Angew. Chem. Int. Ed. 2009, 48, 1304.
74. J. Pavol, D. M. Cockfield, D. J. Dixon, J. Am. Chem. Soc. 2009, 131, 16632.
75. P. Elsner, H. Jiang, J. B. Nielsen, F. Pasi, K. A. Jorgensen, Chem. Commun. 2008, 5827.
76. O. Andrey, A. Vidonne, A. Alexakis, Tetrahedron Lett. 2003, 44, 7901.
77. P. S. Hynes, P. A. Stupple, D. J. Dixon, Org. Lett. 2008, 10, 1389.
78. B.-C. Hong, P. Kotame, C.-W. Tsai, J.-H. Liao, Org. Lett. 2010, 12, 776.
79. S. V. Pansare, R. Lingampally, R. L. Kirby, Org. Lett. 2010, 12, 556.
80. B.-C. Hong, R. Y. Nimje, M.-F. Wu, A. A. Sadani, Eur. J. Org. Chem. 2008, 1149.
81. D. A. Evans, K. T. Chapman, E. A. Carriera, J. Am. Chem. Soc. 1988, 110, 3560.
82. T. Oh-e, N. Miyaura, A. Suzuki, J. Org. Chem. 1993, 58, 2201.
83. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457.
84. M. V. Gill, E. Roman, J. Sorrano, Trends Org. Chem. 2001, 9, 17.
85. Organocatalytic Enantioselective Conjugate Addition Reactions (Eds.:, J. L. Vicario, D. Badia, L. Carrillo, E. Reyes), Royal Society, Cambridge, UK, 2010, chapter 2.