Enantioselective organocatalytic construction of hexahydropyrroloindole by means of α-alkylation of aldehydes leading to the total synthesis of (+)-gliocladin C

Chemistry - A European Journal

Volumn 19, Issue 10, 2013, Pages 3319-3323

  Song, Jin ^a   Guo, Chang ^a   Adele, Arafate ^a   Yin, Hao ^a   Gong, Liu Zhu ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

alkaloids; amines; asymmetric catalysis; phosphoric acid; total synthesis

Indexed keywords

3-HYDROXYOXINDOLES; ASYMMETRIC ALKYLATION; ASYMMETRIC CATALYSIS; CINCHONA ALKALOID; ENANTIOSELECTIVE; ENANTIOSELECTIVE TOTAL SYNTHESIS; ORGANOCATALYTIC; OXINDOLES; TOTAL SYNTHESIS;

ALDEHYDES; ALKALOIDS; AMINES; C (PROGRAMMING LANGUAGE); ENANTIOSELECTIVITY; METABOLITES; NITROGEN COMPOUNDS; PHOSPHORIC ACID; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

2 PYRROLIDONE DERIVATIVE; ALDEHYDE; ALKALOID; ANTINEOPLASTIC AGENT; GLIOCLADIN C; PIPERAZINE DERIVATIVE;

ALKYLATION; ANIMAL; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; LEUKEMIA P 388; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; ALKALOIDS; ALKYLATION; ANIMALS; ANTINEOPLASTIC AGENTS; CATALYSIS; CYCLIZATION; LEUKEMIA P388; MOLECULAR STRUCTURE; PIPERAZINES; PYRROLIDINONES; STEREOISOMERISM;

EID: 84874440796     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201204522     Document Type: Article

References (89)

1. G. A. Cordell, J. E. Saxton, The Alkaloids: Chemistry and Physiology, Vol. 20, New York, 1981, p. 3-295
2. T. Hino, M. Nakagawa, The Alkaloids: Chemistry and pharmacology, Vol. 34, New York, 1989, pp. 1-75
3. T. Sevenet, J. Pusset, The Alkaloids: Chemistry and Pharmacology, Vol. 48, New York, 1996, pp. 1-73
4. U. Anthoni, C. Christophersen, P. H. Nielsen, Alkaloids: chemical and Biological Perspectivese, Vol. 13, NewYork, 1999, pp. 163-236
5. D. Crich, A. Banerjee, Acc. Chem. Res. 2007, 40, 151-161
6. A. Steven, L. E. Overman, Angew. Chem. 2007, 119, 5584-5605
7. Angew. Chem. Int. Ed. 2007, 46, 5488-5508.
8. Y. Usami, J. Yamaguchi, A. Numata, Heterocycles 2004, 63, 1123-1129.
9. D. Greiner, T. Bonaldi, R. Eskeland, E. Roemer, A. Imhof, Nat. Chem. Biol. 2005, 1, 143-145.
10. P. Ruiz-Sanchis, S. A. Savina, F. Albericio, M. Álvarez, Chem. Eur. J. 2011, 17, 1388.
11. A. D. Lebsack, J. T. Link, L. E. Overman, B. A. Stearns, J. Am. Chem. Soc. 2002, 124, 9008-9009
12. L. E. Overman, E. A. Peterson, Angew. Chem. 2003, 115, 2629-2632
13. Angew. Chem. Int. Ed. 2003, 42, 2525-2528
14. J. J. Kodanko, L. E. Overman, Angew. Chem. 2003, 115, 2632-2635
15. Angew. Chem. Int. Ed. 2003, 42, 2528-2531
16. A. Huang, J. J. Kodanko, L. E. Overman, J. Am. Chem. Soc. 2004, 126, 14043-14053
17. J. E. Delorbe, S. Y. Jabri, S. M. Mennen, L. E. Overman, F. Zhang, J. Am. Chem. Soc. 2011, 133, 6549-6552.
18. M. Movassaghi, M. A. Schmidt, Angew. Chem. 2007, 119, 3799-3802
19. Angew. Chem. Int. Ed. 2007, 46, 3725-3728
20. M. Movassaghi, M. A. Schmidt, J. A. Ashehurst, Angew. Chem. 2008, 120, 1507-1509
21. Angew. Chem. Int. Ed. 2008, 47, 1485-1487
22. J. Kim, J. A. Ashenhurst, M. Movassaghi, Science 2009, 324, 238-241
23. J. Kim, M. Movassaghi, J. Am. Chem. Soc. 2010, 132, 14376-14378
24. M. Movassaghi, O. K. Ahmad, S. P. Lathrop, J. Am. Chem. Soc. 2011, 133, 13002-13005.
25. L. E. Overman, Y. Shin, Org. Lett. 2007, 9, 339-341.
26. L. Furst, J. M. R. Narayanam, C. R. J. Stephenson, Angew. Chem. 2011, 123, 9829-9833
27. Angew. Chem. Int. Ed. 2011, 50, 9655-9659.
28. N. Boyer, M. Movassaghi, Chem. Sci. 2012, 3, 1798-1803.
29. B. M. Trost, J. Xie, J. D. Sieber, J. Am. Chem. Soc. 2011, 133, 20611-20622. "
30. G. Guo, J. Song, J. Huang, P. Chen, S. Luo, L. Z. Gong, Angew. Chem. 2012, 124, 1070-1074
31. Angew. Chem. Int. Ed. 2012, 51, 1046-1050.
32. S. Mukherjee, J. W. Yang, S. Hoffmann, B. List, Chem. Rev. 2007, 107, 5471-5569
33. P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232-6265
34. Angew. Chem. Int. Ed. 2008, 47, 6138-6171. For selected examples of alkylation of carbonyl compounds, see
35. R. R. Shaikh, A. Mazzanti, M. Petrini, G. Bartoli, P. Melchiorre, Angew. Chem. 2008, 120, 8835-8838
36. Angew. Chem. Int. Ed. 2008, 47, 8707-8710
37. P. G. Cozzi, F. Benfatti, L. Zoli, Angew. Chem. 2009, 121, 1339-1342
38. Angew. Chem. Int. Ed. 2009, 48, 1313-1316
39. A. Gualandi, E. Emer, M. G. Capdevila, P. G. Cozzi, Angew. Chem. 2011, 123, 7988-7992
40. Angew. Chem. Int. Ed. 2011, 50, 7842-7846
41. F. Benfatti, E. Benedetto, P. G. Cozzi, Chem. Asian J. 2010, 5, 2047
42. L. Zhang, L. Cui, X. Li, J. Li, S. Luo, J.-P. Cheng, Chem. Eur. J. 2010, 16, 2045
43. B. Han, Y.-C. Xiao, Y. Yao, Y.-C. Chen, Angew. Chem. 2010, 122, 10387-10389
44. Angew. Chem. Int. Ed. 2010, 49, 10189-10191
45. J. Xiao, Org. Lett. 2012, 14, 1716-1719.
46. L.-W. Xu, J. Luo, Y. Lu, Chem. Commun. 2009, 1807-1821; for reviews focusing on the reasons that have brought about the development of cinchona-based primary amines, see
47. L. Jiang, Y.-C. Chen, Catal. Sci. Technol. 2011, 1, 354-365
48. G. Bartoli, P. Melchiorre, Synlett 2008, 1759-1771
49. Y.-C. Chen, Synlett 2008, 1919-1930
50. P. Melchiorre, Angew. Chem. 2012, 124, 9886-9909
51. Angew. Chem. Int. Ed. 2012, 51, 9748-9770.
52. W. Chen, W. Du, L. Yue, R. Li, Y. Wu, L.-S. Ding, Y.-C. Chen, Org. Biomol. Chem. 2007, 5, 816-821
53. S. H. McCooey, S. J. Connon, Org. Lett. 2007, 9, 599-602
54. J.-W. Xie, W. Chen, R. Li, M. Zeng, W. Du, L. Yue, Y.-C. Chen, Y. Wu, J. Zhu, J.-G. Deng, Angew. Chem. 2007, 119, 393-396
55. Angew. Chem. Int. Ed. 2007, 46, 389-392
56. G. Bartoli, M. Bosco, A. Carlone, F. Pesciaioli, L. Sambri, P. Melchiorre, Org. Lett. 2007, 9, 1403
57. F. Pesciaioli, F. D. Vincentiis, P. Galzerano, G. Bencivenni, G. Bartoli, A. Mazzanti, P. Melchiorre, Angew. Chem. 2008, 120, 8831-8834
58. Angew. Chem. Int. Ed. 2008, 47, 8703-8706
59. X. Lu, Y. Liu, B. Sun, B. Cindric, L. Deng, J. Am. Chem. Soc. 2008, 130, 8134-8135
60. R. P. Singh, K. Bartelson, Y. Wang, H. Su, X. Lu, L. Deng, J. Am. Chem. Soc. 2008, 130, 2422-2423
61. G. Bencivenni, L. Wu, A. Mazzanti, B. Giannichi, F. Pesciaioli, M. Song, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 7336-7339
62. Angew. Chem. Int. Ed. 2009, 48, 7200-7203
63. L. Wu, G. Bencivenni, M. Mancinelli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 7332-7335
64. Angew. Chem. Int. Ed. 2009, 48, 7196-7199
65. P. Galzerano, F. Pesciaioli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew. Chem. 2009, 121, 8032-8034
66. Angew. Chem. Int. Ed. 2009, 48, 7892-7894
67. G. Bergonzini, S. Vera, P. melchiorre, Angew. Chem. 2010, 122, 9879-9882
68. Angew. Chem. Int. Ed. 2010, 49, 9685-9688
69. G. Bencivenni, P. Galzerano, A. Mazzanti, G. Bartoli, P. Melchiorre, Proc. Natl. Acad. Sci. USA 2010, 107, 20642-20647.
70. M. Rueping, B. J. Nachtsheim, S. A. Moreth, M. Bolte, Angew. Chem. 2008, 120, 603-606
71. Angew. Chem. Int. Ed. 2008, 47, 593-596
72. F. Sun, M. Zeng, Q. Gu, S. You, Chem. Eur. J. 2009, 15, 8709-8712
73. Q.-X. Guo, Y.-G. Peng, J.-W. Zhang, L. Song, Z. Feng, L.-Z. Gong, Org. Lett. 2009, 11, 4620-4623
74. C. Guo, J. Song, L.-Z. Gong, Angew. Chem. 2010, 122, 5690-5694
75. Angew. Chem. Int. Ed. 2010, 49, 5558-5562
76. B. Xu, Z. Guo, W. Jin, Z. Wang, Y. Peng, Q. Guo, Angew. Chem. 2012, 124, 1083-1086
77. Angew. Chem. Int. Ed. 2012, 51, 1059-1062
78. L. Song, Q. Guo, X. Li, J. Tian, Y. Peng, Angew. Chem. 2012, 124, 1935-1938
79. Angew. Chem. Int. Ed. 2012, 51, 1899-1902.
80. J.-W. Xie, X. Huang, L.-P. Fan, D.-C. Xu, X.-S. Li, H. Su, Y.-H. Wen, Adv. Synth. Catal. 2009, 351, 3077-3082.
81. X. Tian, C. Cassani, Y. Liu, A. Moran, A. Urakawa, P. Galzerano, E. Arceo, P. Melchiorre, J. Am. Chem. Soc. 2011, 133, 17934-17941.
82. O. Lifchits, C. M. Reisinger, B. List, J. Am. Chem. Soc. 2010, 132, 10227-10229.
83. D. Uraguchi, M. Terada, J. Am. Chem. Soc. 2004, 126, 5356-5357
84. T. Akiyama, J. Itoh, K. Yokota, K. Fuchibe, Angew. Chem. 2004, 116, 1592-1594
85. Angew. Chem. Int. Ed. 2004, 43, 1566-1568
86. T. Akiyama, Chem. Rev. 2007, 107, 5744-5758
87. A. G. Doyle, E. Jacobsen, Chem. Rev. 2007, 107, 5713-5743
88. M. Terada, Chem. Commun. 2008, 4097-4112
89. M. Terada, Synthesis 2010, 1929-1982.