Synthesis of (±)-Tetrabenazine by Visible Light Photoredox Catalysis

Journal of Organic Chemistry

Volumn 80, Issue 24, 2015, Pages 12635-12640

  Orgren, Lindsey R ^a,b   Maverick, Emily E ^a,c   Marvin, Christopher C ^a,d  

^a HENDRIX COLLEGE   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

^c Veterinary Dentistry and Oral Surgery   (United States)

^d ABBVIE INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; CHEMICAL REACTIONS; CYCLIZATION; ORGANIC SOLVENTS;

AZA-MICHAEL REACTION; BAYLIS-HILLMAN; CARBON-CARBON BOND FORMATION; CYCLIZATION SUBSTRATES; PHOTOREDOX CATALYSIS; TERTIARY AMINE; VISIBLE LIGHT; VISIBLE-LIGHT PHOTOCATALYSIS;

LIGHT;

ACETAL; ACETONITRILE; METHANOL; TERTIARY AMINE; TETRABENAZINE; TETRAHYDROISOQUINOLINE DERIVATIVE; WATER;

ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL BOND; CYCLIZATION; DIASTEREOISOMER; LIGHT; MICHAEL ADDITION; PHOTOCATALYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY;

CATALYSIS; CYCLIZATION; LIGHT; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHOTOCHEMICAL PROCESSES; TETRABENAZINE;

EID: 84952765206     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b02199     Document Type: Article

References (72)

1. Pletscher, A. Science 1957, 126, 507-507 10.1126/science.126.3272.507
2. Brossi, A.; Chopard-dit-Jean, L. H.; Schnider, O. Helv. Chim. Acta 1958, 41, 1793-1806 10.1002/hlca.19580410634
3. Hayden, M. R.; Leavitt, B. R.; Yasothan, U.; Kirkpatrick, P. Nat. Rev. Drug Discovery 2009, 8, 17-18 10.1038/nrd2784
4. Frank, S.; Jankovic, J. Drugs 2010, 70, 561-571 10.2165/11534430-000000000-00000
5. Müller, T. Expert Opin. Invest. Drugs 2015, 24, 737-742 10.1517/13543784.2015.1029573
6. Zheng, G.; Dwoskin, L. P.; Crooks, P. A. AAPS J. 2006, 8, E682-E692 10.1208/aapsj080478
7. Ugolev, Y.; Segal, T.; Yaffe, D.; Gros, Y.; Schuldiner, S. J. Biol. Chem. 2013, 288, 32160-32171 10.1074/jbc.M113.502971
8. Bernstein, A. I.; Stout, K. A.; Miller, G. W. Neurochem. Int. 2014, 73, 89-97 10.1016/j.neuint.2013.12.003
9. Kumar, A.; Lo, S.-T.; Öz, O. K.; Sun, X. Bioorg. Med. Chem. Lett. 2014, 24, 5663-5665 10.1016/j.bmcl.2014.10.070
10. Lin, K.-J.; Weng, Y.-H.; Hsieh, C.-J.; Lin, W.-Y.; Wey, S.-P.; Kung, M.-P.; Yen, T.-C.; Lu, C.-S.; Hsiao, I.-T. PLoS One 2013, 8, e75952 10.1371/journal.pone.0075952
11. Zhu, L.; Liu, J.; Kung, H. F. Bioorg. Med. Chem. Lett. 2009, 19, 5026-5028 10.1016/j.bmcl.2009.07.048
12. Koeppe, R. A.; Gilman, S.; Joshi, A.; Liu, S.; Little, R.; Junck, L.; Heumann, M.; Frey, K. A.; Albin, R. L. J. Nucl. Med. 2005, 46, 936-944
13. Zubieta, J.-K.; Taylor, S. F.; Huguelet, P.; Koeppe, R. A.; Kilbourn, M. R.; Frey, K. A. Biol. Psychiatry 2001, 49, 110-116 10.1016/S0006-3223(00)00981-1
14. Kilbourn, M. R. Nucl. Med. Biol. 1997, 24, 615-619 10.1016/S0969-8051(97)00101-7
15. Kilbourn, M.; Lee, L.; Borght, T. V.; Jewett, D.; Frey, K. Eur. J. Pharmacol. 1995, 278, 249-252 10.1016/0014-2999(95)00162-E
16. Podurgiel, S. J.; Nunes, E. J.; Yohn, S. E.; Barber, J.; Thompson, A.; Milligan, M.; Lee, C. A.; López-Cruz, L.; Pardo, M.; Valverde, O.; Lendent, C.; Baqi, Y.; Müller, C. E.; Correa, M.; Salamone, J. D. Neuroscience 2013, 250, 507-519 10.1016/j.neuroscience.2013.07.008
17. Boldt, K. G.; Biggers, M. S.; Phifer, S. S.; Brine, G. A.; Rehder, K. S. Synth. Commun. 2009, 39, 3574-3585 10.1080/00397910902788125
18. Rishel, M. J.; Amarasinghe, K. K. D.; Dinn, S. R.; Johnson, B. F. J. Org. Chem. 2009, 74, 4001-4004 10.1021/jo900480n
19. Paek, S.-M.; Kim, N.-J.; Shin, D.; Jung, J.-K.; Jung, J.-W.; Chang, D.-J.; Moon, H.; Suh, Y.-G. Chem.-Eur. J. 2010, 16, 4623-4628 10.1002/chem.200902591
20. Yu, Q.-S.; Luo, W.; Deschamps, J.; Holloway, H. W.; Kopajtic, T.; Katz, J. L.; Brossi, A.; Greig, N. H. ACS Med. Chem. Lett. 2010, 1, 105-109 10.1021/ml1000189
21. Son, Y. W.; Kwon, T. H.; Lee, J. K.; Pae, A. N.; Lee, J. Y.; Cho, Y. S.; Min, S.-J. Org. Lett. 2011, 13, 6500-6503 10.1021/ol202792q
22. Johannes, M.; Altmann, K.-H. Org. Lett. 2012, 14, 3752-3755 10.1021/ol301612q
23. Reddy, N. S. S.; Reddy, A. S.; Yadav, J. S.; Reddy, B. V. S. Tetrahedron Lett. 2012, 53, 6916-6918 10.1016/j.tetlet.2012.10.017
24. Lee, L. C.; Vander Borght, T.; Sherman, P. S.; Frey, K. A.; Kilbourn, M. R. J. Med. Chem. 1996, 39, 191-196 10.1021/jm950117b
25. Boldt, K. G.; Brine, G. A.; Rehder, K. Org. Prep. Proced. Int. 2008, 40, 379-384 10.1080/00304940809458097
26. Yao, Z.; Wei, X.; Wu, X.; Katz, J. L.; Kopajtic, T.; Greig, N. H.; Sun, H. Eur. J. Med. Chem. 2011, 46, 1841-1848 10.1016/j.ejmech.2011.02.046
27. Zheng, P.; Lieberman, B. P.; Choi, S. R.; Plöessl, K.; Kung, H. F. Bioorg. Med. Chem. Lett. 2011, 21, 3435-3438 10.1016/j.bmcl.2011.03.113
28. Burns, N. Z.; Baran, P. S.; Hoffmann, R. W. Angew. Chem., Int. Ed. 2009, 48, 2854-2867 10.1002/anie.200806086
29. Modern Oxidation Methods, 2nd ed.; Bäckvall, J.-E., Ed.; Wiley-VCH: Weinheim, 2011.
30. Boess, E.; Schmitz, C.; Klussmann, M. J. Am. Chem. Soc. 2012, 134, 5317-5325 10.1021/ja211697s
31. Sureshkumar, D.; Sud, A.; Klussmann, M. Synlett 2009, 2009, 1558-1561 10.1055/s-0029-1217336
32. Shen, Y.; Tan, Z.; Chen, D.; Feng, X.; Li, M.; Guo, C.-C.; Zhu, C. Tetrahedron 2009, 65, 158-163 10.1016/j.tet.2008.10.078
33. Shen, Y.; Li, M.; Wang, S.; Zhan, T.; Tan, Z.; Guo, C.-C. Chem. Commun. 2009, 953-955 10.1039/b819657e
34. Zeng, T.; Song, G.; Moores, A.; Li, C.-J. Synlett 2010, 2010, 2002-2008 10.1055/s-0030-1258128
35. Ratnikov, M. O.; Xu, X.; Doyle, M. P. J. Am. Chem. Soc. 2013, 135, 9475-9479 10.1021/ja402479r
36. Huo, C.; Wu, M.; Jia, X.; Xie, H.; Yuan, Y.; Tang, J. J. Org. Chem. 2014, 79, 9860-9864 10.1021/jo5017822
37. Dhineshkumar, J.; Lamani, M.; Alagiri, K.; Prabhu, K. R. Org. Lett. 2013, 15, 1092-1095 10.1021/ol4001153
38. Nobuta, T.; Fujiya, A.; Yamaguchi, T.; Tada, N.; Miura, T.; Itoh, A. RSC Adv. 2013, 3, 10189-10192 10.1039/c3ra41850b
39. Tanoue, A.; Yoo, W.-J.; Kobayashi, S. Org. Lett. 2014, 16, 2346-2349 10.1021/ol500661t
40. Beatty, J. W.; Stephenson, C. R. J. Acc. Chem. Res. 2015, 48, 1474-1484 10.1021/acs.accounts.5b00068
41. Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1239176 10.1126/science.1239176
42. Jahn, E.; Jahn, U. Angew. Chem., Int. Ed. 2014, 53, 13326-13328 10.1002/anie.201408748
43. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322-5363 10.1021/cr300503r
44. Shi, L.; Xia, W. Chem. Soc. Rev. 2012, 41, 7687-7697 10.1039/c2cs35203f
45. Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828-6838 10.1002/anie.201200223
46. Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527-532 10.1038/nchem.687
47. Condie, A. G.; Gonzalez-Gomez, J. C.; Stephenson, C. R. J. J. Am. Chem. Soc. 2010, 132, 1464-1465 10.1021/ja909145y
48. Rueping, M.; Zhu, S.; Koenigs, R. M. Chem. Commun. 2011, 47, 12709-12711 10.1039/c1cc15643h
49. Hari, D. P.; König, B. Org. Lett. 2011, 13, 3852-3855 10.1021/ol201376v
50. Xuan, J.; Feng, Z.-J.; Duan, S.-W.; Xiao, W.-J. RSC Adv. 2012, 2, 4065-4068 10.1039/c2ra20403g
51. Rueping, M.; Koenigs, R. M.; Poscharny, K.; Fabry, D. C.; Leonori, D.; Vila, C. Chem.-Eur. J. 2012, 18, 5170-5174 10.1002/chem.201200050
52. DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094-8097 10.1021/ja3030164
53. Nie, S.-Z.; Sun, X.; Wei, W.-T.; Zhang, X.-J.; Yan, M.; Xiao, J.-L. Org. Lett. 2013, 15, 2394-2397 10.1021/ol4008469
54. Mathis, C. L.; Gist, B. M.; Frederickson, C. K.; Midkiff, K. M.; Marvin, C. C. Tetrahedron Lett. 2013, 54, 2101-2104 10.1016/j.tetlet.2013.02.031
55. Miller, L. L.; Stermitz, F. R.; Becker, J. Y.; Ramachandran, V. J. Am. Chem. Soc. 1975, 97, 2922-2923 10.1021/ja00843a063
56. Baslé, O.; Borduas, N.; Dubois, P.; Chapuzet, J. M.; Chan, T.-H.; Lessard, J.; Li, C.-J. Chem.-Eur. J. 2010, 16, 8162-8166 10.1002/chem.201000240
57. Chow, P.-K.; To, W.-P.; Low, K.-H.; Che, C.-M. Chem.-Asian J. 2014, 9, 534-545 10.1002/asia.201301059
58. Jones, K. M.; Klussmann, M. Synlett 2012, 2012, 159-162 10.1055/s-0031-1290117
59. Freeman, D. B.; Furst, L.; Condie, A. G.; Stephenson, C. R. J. Org. Lett. 2012, 14, 94-97 10.1021/ol202883v
60. Zhao, G.; Yang, C.; Guo, L.; Sun, H.; Chen, C.; Xia, W. Chem. Commun. 2012, 48, 2337-2339 10.1039/c2cc17130a
61. Rueping, M.; Vila, C.; Koenigs, R. M.; Poscharny, K.; Fabry, D. C. Chem. Commun. 2011, 47, 2360-2362 10.1039/C0CC04539J
62. Pan, Y.; Kee, C. W.; Chen, L.; Tan, C.-H. Green Chem. 2011, 13, 2682-2685 10.1039/c1gc15489c
63. Kohls, P.; Jadhav, D.; Pandey, G.; Reiser, O. Org. Lett. 2012, 14, 672-675 10.1021/ol202857t
64. Perepichka, I.; Kundu, S.; Hearne, Z.; Li, C.-J. Org. Biomol. Chem. 2015, 13, 447-451 10.1039/C4OB02138J
65. Rusch, F.; Unkel, L.-N.; Alpers, D.; Hoffmann, F.; Brasholz, M. Chem.-Eur. J. 2015, 21, 8336-8340 10.1002/chem.201500612
66. Andrews, R. S.; Becker, J. J.; Gagné, M. R. Org. Lett. 2011, 13, 2406-2409 10.1021/ol200644w
67. Bouzide, A. Org. Lett. 2002, 4, 1347-1350 10.1021/ol020032m
68. Baker, B. A.; Bošković, Ž. V.; Lipshutz, B. H. Org. Lett. 2008, 10, 289-292 10.1021/ol702689v
69. Pelšs, A.; Kumpulainen, E. T. T.; Koskinen, A. M. P. J. Org. Chem. 2009, 74, 7598-7601 10.1021/jo9017588
70. Ashby, E. C.; Lin, J. J. Tetrahedron Lett. 1975, 16, 4453-4456 10.1016/S0040-4039(00)91090-6
71. Ashby, E. C.; Lin, J. J.; Kovar, R. J. Org. Chem. 1976, 41, 1939-1943 10.1021/jo00873a011
72. Leonard, W. R.; Livinghouse, T. J. Org. Chem. 1985, 50, 730-732 10.1021/jo00205a048