Synthetic studies on statins. Part 1: A short and cyanide-free synthesis of atorvastatin calcium via an enantioselective aldol strategy

Tetrahedron Asymmetry

Volumn 24, Issue 4, 2013, Pages 207-211

  Hu, Lemeng ^a   Xiong, Fangjun ^a   Chen, Xiaofei ^a   Chen, Wenxue ^a   He, Qiuqin ^a   Chen, Fener ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACROLEIN; ATORVASTATIN; SCHIFF BASE;

ADDITION REACTION; ALDOL REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; DRUG STRUCTURE; ENANTIOMER; ENANTIOSELECTIVITY; HYDROGENATION; POLYMERIZATION; PRIORITY JOURNAL; STEREOCHEMISTRY; TEMPERATURE;

EID: 84874625750     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.12.009     Document Type: Article

References (70)

1. A. Graul, and J. Castaner Drugs Future 22 1997 956
2. E.S. Istvan, and J. Deisenhofer Science 292 2001 1160
3. Z. Časar Curr. Org. Chem. 14 2010 816
4. P.L. Brower, D.E. Butler, C.F. Deering, T.V. Le, A. Millar, T.N. Nanninga, and B.D. Roth Tetrahedron Lett. 33 1992 2279
5. G. Wess, K. Kesseler, E. Baader, W. Bartmann, G. Beck, A. Bergmann, H. Jendralla, K. Bock, O. Holzstein, H. Kleine, and M. Schnierer Tetrahedron Lett. 31 1990 2545
6. T. Konoike, and Y. Araki J. Org. Chem. 59 1994 7849
7. Cho, Y.-H.; Roh, K. R.; Shin, J. H.; Chun, J. P.; Yu, H. S.; Cho, C.-W. WO 2002096915, 2002.
8. T. Konoike, T. Okada, and Y. Araki J. Org. Chem. 63 1998 3037
9. M. Sletzinger, T.R. Verhoeven, R.P. Volante, J.M. McNamara, E.G. Corley, and T.M.H. Liu Tetrahedron Lett. 26 1985 2951
10. Millar, A.; Butler, D. E. US 5103024, 1992.
11. S. Rádl Synth. Commun. 33 2003 2275
12. K.L. Baumann, D.E. Butler, C.F. Deering, K.E. Mennen, A. Millar, T.N. Nanninga, C.W. Palmer, and B.D. Roth Tetrahedron Lett. 33 1992 2283
13. Thottathil, J. K.; Pendri, Y.; Li, W.-S.; Kronenthal D. R. US 5278313, 1994.
14. Butler, D. E.; Le, T. V.; Millar, A.; Nanninga, T. N. US 5155251, 1992.
15. H. Jendralla, E. Granzer, B.V. Kerekjarto, R. Krause, U. Schacht, E. Baader, W. Bartmann, G. Beck, A. Bergmann, K. Kesseler, G. Wess, L.J. Chen, S. Granata, J. Herchen, H. Kleine, H. Schussler, and K. Wagner J. Med. Chem. 34 1991 2962
16. H. Shin, B.S. Choi, K.K. Lee, H. Choi, J.H. Chang, K.W. Lee, D.H. Nam, and N.S. Kim Synthesis 16 2004 2629
17. D.M. Bowles, G.L. Bolton, D.C. Boyles, T.T. Curran, R.H. Hutchings, S.D. Larsen, J.M. Miller, W.K.C. Park, K.G. Ritsema, and D.C. Schineman Org. Process Res. Dev. 12 2008 1183
18. Lim, Y. M.; Han, Y. T.; Lee, B. G.; Song, Y. S. WO 2009054693, 2009.
19. Khamar, B. M.; Prabhakar, M. T.; Bapat, U. R.; Siddiqui, I. H.; Modi, I. A. WO 2011101816, 2011.
20. Lange, D. B.; Elsenberg, H. L. M. WO 2012032035, 2012.
21. B.D. Roth, C.J. Blankley, A.W. Chucholowski, E. Ferguson, M.L. Hoefle, D.F. Ortwine, R.S. Newton, C.S. Sekerke, D.R. Sliskovic, C.D. Stratton, and M.W. Wilson J. Med. Chem. 34 1991 357
22. M. Braun, and R. Devant Tetrahedron Lett. 25 1984 5031
23. Roth, B. D. US 5273995, 1993.
24. Mills, N.; Muhammad, N.A.; Weiss, J.; Nesbitt, R. WO 9416693, 1994.
25. Nelson, J. D.; Pamment, M. G. WO 2004089894, 2004.
26. H. Jendralla, E. Baader, W. Bartmann, G. Beck, A. Bergmann, E. Granzer, Bv Kerekjarto, K. Kesseler, R. Krause, W. Schubert, and G. Wess J. Med. Chem. 33 1990 61
27. J.E. Lynch, R.P. Volante, R.V. Wattley, and I. Shinkai Tetrahedron Lett. 28 1987 1385
28. D.A. Evans, W.C. Trenkle, J. Zhang, and J.D. Burch Org. Lett. 7 2005 3335
29. D.A. Evans, M.C. Kozlowski, J.A. Murry, C.S. Burgey, K.R. Campos, B.T. Connell, and R.J. Staples J. Am. Chem. Soc. 121 1999 669
30. Butler, D. E.; Dejong, R. L.; Nelson, J. D.; Pamment, M. G.; Stuk, T. L. WO 2002055519, 2002.
31. J. Krüger, and E.M. Carreira J. Am. Chem. Soc. 120 1998 837
32. Y. Kawato, M. Iwata, R. Yazaki, N. Kumagai, and M. Shibasaki Tetrahedron 67 2011 6539
33. N. Andrushko, V. Andrushko, V. Tararov, A. Korostylev, G. König, and A. Börner Chirality 22 2010 534
34. P. Sawant, and M.E. Maier Tetrahedron 66 2010 9738
35. W. Fan, W. Li, X. Ma, X. Tao, X. Li, Y. Yao, X. Xie, and Z. Zhang J. Org. Chem. 76 2011 9444
36. Shibasaki, M.; Kumagai, N. WO 2012114926, 2012.
37. M. Müller Angew. Chem., Int. Ed. 44 2005 362
38. J. Liu, C.-C. Hsu, and C.-H. Wong Tetrahedron Lett. 45 2004 2439
39. H.J.M. Gijsen, and C.-H. Wong J. Am. Chem. Soc. 116 1994 8422
40. H.J.M. Gijsen, and C.-H. Wong J. Am. Chem. Soc. 117 1995 7585
41. A.R. Moen, B.H. Hoff, L.K. Hansen, T. Anthonsen, and E.E. Jacobsen Tetrahedron: Asymmetry 15 2004 1551
42. S. Bergeron, D.A. Chaplin, J.H. Edwards, B.S.W. Ellis, C.L. Hill, K. Holt-Tiffin, J.R. Knight, T. Mahoney, A.P. Osborne, and G. Ruecroft Org. Process Res. Dev. 10 2006 661
43. M. Wolberg, I.A. Kaluzna, M. Müller, and J.D. Stewart Tetrahedron: Asymmetry 15 2004 2825
44. Giver, L. J.; Newman, L. M.; Mundorff, E. WO 2008042876, 2008.
45. S.K. Ma, J. Gruber, C. Davis, L. Newman, D. Gray, A. Wang, J. Grate, G.W. Huisman, and R.A. Sheldon Green Chem. 12 2010 81
46. X. Wu, L. Wang, S. Wang, and Y. Chen Amino Acids 39 2010 305
47. B.M. Trost, and C.S. Brindle Chem. Soc. Rev. 39 2010 1600
48. L.M. Geary, and P.G. Hultin Tetrahedron: Asymmetry 20 2009 131
49. Z. Miao, and F. Chen Synthesis 2012 2506
50. B. Alcaide, and P. Almendros Eur. J. Org. Chem. 2002 1595
51. T.D. Machajewski, and C.-H. Wong Angew. Chem., Int. Ed. 39 2000 1352
52. M. Hayashi, K. Yoshimoto, N. Hirata, K. Tanaka, N. Oguni, K. Harada, A. Matsushita, Y. Kawachi, and H.Isr Sasaki J. Chem. 41 2001 241
53. J.T. Zacharia, T. Tanaka, and M. Hayashi J. Org. Chem. 75 2010 7514
54. M. Hayashi, T. Inoue, and N. Oguni J. Chem. Soc., Chem. Commun. 1994 341
55. C. Chu, K. Morishita, T. Tanaka, and M. Hayashi Tetrahedron: Asymmetry 17 2006 2672
56. P.A. Clarke, S. Santos, N. Mistry, L. Burroughs, and A.C. Humphries Org. Lett. 13 2011 624
57. N. Oguni, K. Tanaka, and H. Ishida Synlett 1998 601
58. T. Kawase, S. Takizawa, D. Jayaprakash, and H. Sasai Synth. Commun. 34 2004 4487
59. M. Hayashi, K. Tanaka, and N. Oguni Tetrahedron: Asymmetry 1995 1833 6
60. M. Hayashi, H. Kaneda, and N. Oguni Tetrahedron: Asymmetry 6 1995 2511
61. R.M. Moreno, and A. Moyano Tetrahedron: Asymmetry 17 2006 1104
62. E.J. Corey, D. Barnes-Seeman, and T.W. Lee Tetrahedron Lett. 38 1997 4351
63. H. Griesser, R. Öhrlein, W. Schwab, R. Ehrler, and V. Jäger Org. Synth. 77 2000 236
64. Schoening, K.-U.; Hartwig, J. WO 03004457, 2003.
65. Pai, G. G.; Nanda, K.; Chaudhari, N. P.; Anjaneyulu, A.; Ghogare, B. N. WO 2009144736, 2009.
66. Butler, D. E.; Deering, C. F.; Millar. A.; Nanninga, T. N.; Roth, B. D. WO 8907598, 1989.
67. M. Hayashi, Y. Miyamoto, T. Inoue, and N. Oguni J. Chem. Soc., Chem. Commun. 1991 1752
68. M. Hayashi, Y. Miyamoto, T. Inoue, and N. Oguni J. Org. Chem. 58 1993 1515
69. K. Narasaka, and F.C. Pai Tetrahedron 40 1984 2233
70. K.M. Chen, G.E. Hardmann, K. Prasada, O. Repič, and M.J. Shapiro Tetrahedron Lett. 28 1987 155