Synthesis of (+)-phenserine using an interrupted Fischer indolization reaction

Journal of Organic Chemistry

Volumn 77, Issue 1, 2012, Pages 725-728

  Schammel, Alex W ^a   Chiou, Grace ^a   Garg, Neil K ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALZHEIMER; CONCISE SYNTHESIS; INDOLIZATION;

CHEMISTRY; ORGANIC COMPOUNDS;

SYNTHESIS (CHEMICAL);

PHENSERINE;

ALZHEIMER DISEASE; ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; INTERRUPTED FISCHER INDOLIZATION; RACEMIZATION; STRUCTURE ACTIVITY RELATION; SUPERCRITICAL FLUID CHROMATOGRAPHY;

ALZHEIMER DISEASE; CHOLINESTERASE INHIBITORS; INDOLES; MOLECULAR STRUCTURE; PHYSOSTIGMINE; PYRROLIDINES; STEREOISOMERISM;

EID: 84855522290     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo202078z     Document Type: Article

References (41)

1. Takano, S.; Ogasawara, K. Alkaloids 1989, 36, 225-251
2. Greig, N. H.; Pei, X.-F.; Soncrant, T. T. Med. Res. Rev. 1995, 15, 3-31
3. Schönenberger, B.; Brossi, A.; George, C.; Flippen-Anderson, J. L. Helv. Chim. Acta 1986, 69, 283-287
4. Takano, S.; Moriya, M.; Ogasawara, K. J. Org. Chem. 1991, 56, 5982-5984
5. Pei, X.-F.; Greig, N. H.; Flippen-Anderson, J. L.; Bi, S.; Brossi, A. Helv. Chim. Acta 1994, 77, 1412-1422
6. Node, M.; Hao, X.-J.; Nishide, K.; Fuji, K. Chem. Pharm. Bull. 1996, 44, 715-719
7. Yu, Q.-S.; Pei, X.-F.; Holloway, H. W.; Greig, N. H. J. Med. Chem. 1997, 40, 2895-2901
8. Matsuura, T.; Overman, L. E.; Poon, D. J. J. Am. Chem. Soc. 1998, 120, 6500-6503
9. Yu, Q.-S.; Brossi, A. Heterocycles 1988, 27, 745-750
10. Huang, A.; Kodanko, J. J.; Overman, L. E. J. Am. Chem. Soc. 2004, 126, 14043-14053
11. Nishida, A.; Ushigome, S.; Sugimoto, A.; Arai, S. Heterocycles 2005, 66, 181-185
12. Trost, B. M.; Quancard, J. J. Am. Chem. Soc. 2006, 128, 6314-6315
13. Nakao, Y.; Ebata, S.; Yada, A.; Hiyama, T.; Ikawa, M.; Ogoshi, S. J. Am. Chem. Soc. 2008, 130, 12874-12875
14. Bui, T.; Syed, S.; Barbas, C. F., III. J. Am. Chem. Soc. 2009, 131, 8758-8759
15. Trost, B. M.; Zhang, Y. Chem.-Eur. J. 2011, 17, 2916-1922
16. For a recent synthesis of (±)-phenserine, see: Rigby, J. H.; Sidique, S. Org. Lett. 2007, 9, 1219-1221
17. Polonovski, M. Bull. Soc. Chim. Fr. 1916, 19, 47
18. Yu, Q.-S.; Schönenberger, B.; Brossi, A. Heterocycles 1987, 26, 1271-1275
19. Greig, N. H.; Sambamurti, K.; Yu, Q.-S.; Brossi, A.; Bruinsma, G. B.; Lahiri, D. K. Curr. Alzeheimer Res. 2005, 2, 281-290
20. Becker, R. E.; Greig, N. H. Curr. Alzeheimer Res. 2010, 7, 642-651
21. Lahiri, D. K.; Chen, D.; Maloney, B.; Holloway, H. W.; Yu, Q.-S.; Utsuki, T.; Giordano, T.; Sambamurti, K.; Greig, N. H. J. Pharmacol. Exp. Ther. 2007, 320, 396-396
22. QR Pharma, Inc. Home Page. http://www.qrpharma.com/ (accessed September 15, 2011).
23. Boal, B. W.; Schammel, A. W.; Garg, N. K. Org. Lett. 2009, 11, 3458-3461
24. Schammel, A. W.; Boal, B. W.; Zu, L.; Mesganaw, T.; Garg, N. K. Tetrahedron 2010, 66, 4687-4695
25. Çelebi-Ölçüm, N.; Boal, B. W.; Huters, A. D.; Garg, N. K.; Houk, K. N. J. Am. Chem. Soc. 2011, 133, 5752-5755
26. Zu, L.; Boal, B. W.; Garg, N. K. J. Am. Chem. Soc. 2011, 133, 8877-8879
27. Bronner, S. M.; Goetz, A. E.; Garg, N. K. J. Am. Chem. Soc. 2011, 133, 3832-3835
28. Huters, A. D.; Quasdorf, K. W.; Styduhar, E.; Garg, N. K. J. Am. Chem. Soc. 2011, 133, 15797-15799
29. Fischer, E.; Jourdan, F. Berichte 1883, 16, 2241-2245
30. Fischer, E.; Hess, O. Ber. 1884, 17, 559-568
31. Grandberg, I. I.; Zuyanova, T. I.; Afonina, N. I.; Ivanova, T. A. Dokl. Akad. Nauk SSSR 1967, 176, 583-585
32. Grandberg, I. I.; Tokmakov, G. P. Khim. Geterotsikl. Soedin. 1975, 207-210
33. Takano, S.; Moriya, M.; Iwabuchi, Y.; Ogasawara, K. Chem. Lett. 1990, 109-112
34. Takano, S.; Ogasawara, K.; Iwabuchi, R.; Moriya, M. JP 03112989 A 19910514, 1991.
35. Rosenmund, P.; Gektidis, S.; Brill, H.; Kalbe, R. Tetrahedron Lett. 1989, 30, 61-62
36. Mesganaw, T.; Zu, L.; Garg, N. K. University of California, Los Angeles, CA. Unpublished work, 2010. For a chiral auxilary approach toward (-)-esermethole and other related pyrrolidinoindolines, see ref 2i.
37. Menezes, R.; Smith, M. B. Synth. Commun. 1988, 18, 1625-1636
38. Mader, M.; Helquist, P. Tetrahedron Lett. 1988, 29, 3049-3052
39. Srivastava, S.; Ruane, P. H.; Toscano, J. P.; Sullivan, M. B.; Cramer, C. J.; Chiapperino, D.; Reed, E. C.; Falvey, D. E. J. Am. Chem. Soc. 2000, 122, 8271-8278
40. Tsuji, R.; Nakagawa, M.; Nishida, A. Heterocycles 2002, 58, 587-594
41. Pallavicini, M.; Valoti, E.; Villa, L.; Lianza, F. Tetrahedron: Asymmetry 1994, 5, 111-116