A Concise Total Synthesis of (R)-Fluoxetine, a Potent and Selective Serotonin Reuptake Inhibitor
Keywords:
Fluoxetine, serotonin reuptake inhibitor, catalytic asymmetric allylationAbstract
Abstract. (R)-Fluoxetine, potent and selective serotonin reuptake inhibitor, has been synthesized in six steps, 50% overall yield and 99% ee from benzaldehyde via catalytic asymmetric allylation with Maruoka´s catalyst.
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References
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2. Lapis, A. A. M.; de Fátima, A.; Martins, J. E. D.; Costa, V. E. U.; Pilli, R. A.; Tetrahedron Lett. 2005, 46, 495.
3. Robertson, D.A.; Krushinski, J.H.; Fuller, R.W.; Leander, J. D.; J. Med. Chem. 1988, 31, 1412.
4. Robertson, D. W.; Jones, N. D.; Swartzendruber, J. K.; Yang, K. S.; Wong, D. T.; J. Med. Chem. 1988, 31, 185.
5. Murphy, D.L.; Mueller, E.A.; Garrick, N.A.; Aulakh, C.S.; J. Clin. Psychiatry 1986, 47, 9.
6. Wilde, M. I.; Benfield, P.; Pharmacoeconomics 1998, 13, 543.
7. Montgomery, S. A.; Int. Clin. Psychopharmacol. 1998, 13, S49.
8. Garrison, G. D.; Levin, G. M.; Ann. Pharmacother. 2000, 34, 10.
9. Bianchi, M.; Sacerdote, P.; Panerai, A. E.; Eur. J. Pharmacol. 1994¸ 263, 81.
10. Bianchi, M.; Rossoni, G.; Sacerdote, P.; Panerai, A. E.; Berti, E.; Inflamm. Res. 1995, 44, 466.
11. Sawynok, J.; Esser, M. J.; Reid, A. R.; Pain 1999, 82, 149.
12. Abdel-Salam, O. M. E.; Baiuomy, A. R.; Arbid, M. S.; Pharmacol. Res. 2004, 49, 119.
13. Some recent processes for preparing fluoxetine or intermediates for its total synthesis: Wallace, H. J.; Hugh, S. C.; Roger, J. A.; AU Patent 4579399, 2000; Wallace, H. J.; Roger, J. A.; WO
Patent 0007976, 2000; Xin, C.; Jingen, D.; Tongfei, W.; CN Patent 1294120, 2001; Wallace, H. J.; Roger, J. A.; Hugh, S. C.; US Patent 6028224, 2000; Bhasker, K. G.; Vijaya, R. K.; Venkateswara, R. M.; GB Patent 2387597, 2003.
14. Pandey, R. K.; Fernades, R. A.; Kumar, P.; Tetrahedron Lett. 2002, 43, 4425.
15. Gao, Y.; Sharpless, K. B.; J. Org. Chem. 1988, 53, 4081.
16. Kakei, H.; Nemoto, T.; Ohshima, T.; Shibasaki, M.; Angew. Chem. Int. Ed. 2004, 43, 317.
17. Mitchell, D.; Koenig, T. M.; Syn. Comm. 1995, 25, 1231.
18. Hilbon, J. W.; Lu, Z. H.; Jurgens, A. R.; Fang, Q. K.; Byers, P.; Wald, S. A.; Senanayake, C. H.; Tetrahedron Lett. 2001, 42, 8919.
19. Devocelle, M.; Agbossou, F.; Mortreux, A.; Synlett 1997¸ 1306.
20. Sakuraba, S.; Achiwa, K.; Chem. Pharm. Bull. 1995, 43, 748.
21. Sakuraba, S.; Achiwa, K.; Synlett 1991¸ 689.
22. Srebnik, M.; Ramachandran, P.V.; Brown, H.C.; J. Org. Chem. 1988, 59, 2916.
23. Corey, E. J.; Reichard, G. A.; Tetrahedron Lett. 1989, 30, 5207.
24. Gu, J.-X.; Li, Z.-Y.; Lin, G.-Q.; Tetrahedron 1993, 49, 5805.
25. Boaz, N. W.; J. Org. Chem. 1992, 57, 4289.
26. Schneider, M.P.; Goergens, U.; Tetrahedron: Asymmetry 1992, 3, 525.
27. Kumar, A.; Ner, D.H.; Dike, S. Y.; Tetrahedron Lett. 1991, 32, 1901.
28. Chenevert, R.; Fortier, G.; Chem. Lett. 1991, 1603.
29. Devine, P. N.; Heid, R. M.; Tschaen Jr., D. M.; Tetrahedron 1997, 53, 6739.
30. Miles, W. H.; Fialcowitz, E. J.; Halstead, E. S.; Tetrahedron 2001, 57, 9925.
31. Bracher, F.; Litz, T.; Bioorg. Med. Chem. 1996, 4, 877.
32. Master, H. E.; Newadkar, R. V.; Rane, R. A.; Kumar, A.; Tetrahedron Lett. 1996¸ 37, 9253.
33. Ali, I. S.; Sudalai, A.; Tetraheron Lett. 2002, 43, 5435.
34. Koenig, T.M.; Mitchell, D.; Tetrahedron Lett. 1994, 35, 1339.
35. Trost, B.; Proc. Natl. Acad. Sci. USA 2004, 101, 5348.
36. Correa, I. R.; Pilli, R. A.; Quim. Nova 2003, 26, 531.
37. Denmark, S. E.; Fu, J.; Chem. Rev. 2003, 103, 2763.
38. de Fátima, A.; Pilli, R. A.; Arkivoc 2003, 10, 118.
39. de Fátima, A.; Pilli, R. A.; Tetrahedron Lett. 2003, 44, 8721.
40. de Fátima, A.; Kohn, L. K.; Antônio, M. A.; de Carvalho, J. E.; Pilli, R. A.; Bioorg. Med. Chem. 2004, 12, 5437.
41. Hanawa, H.; Hashimoto, T.; Maruoka, K.; J. Am. Chem. Soc. 2003¸ 125, 1708.
42. Yanagisawa, A.; Nakashima, H.; Nakatsuka, Y.; Ishiba, A.; Yamamoto, H.; Bull. Chem. Soc. Jpn. 2001, 74, 1129.
43. Pappo, R.; Jr. Allen, D. S.; Lemieux, R. U.; Johnson, W. S.; J. Org. Chem. 1956, 21, 478.
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2020-08-07
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