Synthesis of (±)-7-hydroxylycopodine

Journal of Organic Chemistry

Volumn 77, Issue 17, 2012, Pages 7143-7156

  Lin, Hong Yu ^a   Causey, Robert ^b   Garcia, Gregory E ^b   Snider, Barry B ^a  

^a BRANDEIS UNIVERSITY   (United States)

^b US ARMY MEDICAL RESEARCH INSTITUTE OF CHEMICAL DEFENSE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDIC CONDITIONS; AMINO-PHENOLS; COMPLETE CONTROL; NEUTRAL CONDITIONS; ONE-POT PROCEDURES; OXAZOLIDINES; PRIMARY ALCOHOLS; PRINS REACTION; PT-CATALYZED; RING FUSION; TERTIARY ALCOHOLS;

AMIDES; BENZENE; ETHERS; HYDROGENATION; MANGANESE; PHENOLS; PLATINUM; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

SULFURIC ACID;

7 HYDROXYLYCOPODINE; 7,8 DIHYDROXYLYCOPODINE; ACETYLCHOLINESTERASE; ALCOHOL; BENZENE; BENZOPHENONE; CHOLINESTERASE INHIBITOR; HYDROXYLATE; OXAZOLIDINE DERIVATIVE; PALLADIUM; PYRIDINE; SULFURIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ENZYME INHIBITION; HEATING; HYDROGENATION; ISOMERIZATION; OXIDATION; PROTON TRANSPORT; STEREOCHEMISTRY;

ALKALOIDS; MOLECULAR STRUCTURE; QUINOLIZINES; STEREOISOMERISM;

EID: 84866066339     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo300353t     Document Type: Article

References (91)

1. Kobayashi, J.; Morita, H. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Elsevier: San Diego, CA, 2005; Vol. 61, pp 1-57.
2. Ma, X.; Gang, D. R. Nat. Prod. Rep. 2004, 21, 752-772
3. Hirasawa, Y.; Kobayashi, J.; Morita, H. Heterocycles 2009, 77, 679-729
4. Tang, X. C.; Han, Y. F. CNS Drug Rev. 1999, 5, 281-300
5. Hostettmann, K.; Borloz, A.; Urbain, A.; Marston, A. Curr. Org. Chem. 2006, 10, 825-847
6. Zhu, D.-Y.; Tan, C.-H.; Li, Y.-M. In Medicinal Chemistry of Bioactive Natural Products; Liang, X.-T.; Fang, W.-S., Eds.; Wiley-VCH: New York, 2006; pp 143-182.
7. Bai, D. Pure Appl. Chem. 2007, 79, 469-479
8. Little, J. T.; Walsh, S.; Aisen, P. S. Expert Opin. Invest. Drugs 2008, 17, 209-215
9. Desilets, A. R.; Gickas, J. J.; Dunican, K. C. Ann. Pharmacother. 2009, 43, 514-518
10. Ha, G.-T.; Wong, R.-K.; Zhang, Y. Chem. Biodiversity 2011, 8, 1189-1204
11. Ortega, M. G.; Agnese, A. M.; Cabrera, J. L. Tetrahedron Lett. 2004, 45, 7003-7005
12. Ortega, M. G.; Agnese, A. M.; Barboza, G. E.; Cabrera, J. L. J. Argent. Chem. Soc. 2007, 95, 1-9
13. Vallejo, M. G.; Ortega, M. G.; Cabrera, J. L.; Carlini, V. P.; Rubiales de Barioglio, S.; Almiron, R. S.; Ramirez, O. A.; Agnese, A. M. J. Nat. Prod. 2009, 72, 156-158 (note that the methyl group of sauroine is attached to the wrong carbon)
14. Ortega, M. G.; Vallejo, M. G.; Agnese, A. M.; Cabrera, J. L. Recent Prog. Med. Plants 2010, 29, 345-362
15. Tan, C.-H. Ph.D. Thesis, Shanghai Institute of Materia Medica, 2001.
16. Tan, C.-H.; Zhu, D.-Y. Helv. Chim. Acta 2004, 87, 1963-1967
17. Stork, G.; Kretchmer, R. A.; Schlessinger, R. H. J. Am. Chem. Soc. 1968, 90, 1647-1648
18. Ayer, W. A.; Bowman, W. R.; Joseph, T. C.; Smith, P. J. Am. Chem. Soc. 1968, 90, 1648-1650
19. Kim, S.; Bando, Y.; Horii, Z. Tetrahedron Lett. 1978, 2293-2294
20. Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. J. Am. Chem. Soc. 1978, 100, 8036-8037
21. 1982, 104, 1054-1068.
22. Schumann, D.; Müller, H.-J.; Naumann, A. Liebigs Ann. Chem. 1982, 1700-1705
23. Kraus, G. A.; Hon, Y. S. J. Am. Chem. Soc. 1985, 107, 4341-4342
24. Heterocycles 1987, 25, 377-386.
25. Padwa, A.; Brodney, M. A.; Marino, J. P.; Sheehan, S. M. J. Org. Chem. 1997, 62, 78-87
26. Greico, P. A.; Dai, Y. J. J. Am. Chem. Soc. 1998, 120, 5128-5129
27. Mori, M.; Hori, K.; Akashi, M.; Hori, M.; Sato, Y.; Nishida, M. Angew. Chem., Int. Ed. 1998, 37, 636-637
28. Yang, H.; Carter, R. G.; Zakharov, L. N. J. Am. Chem. Soc. 2008, 130, 9238-9239
29. Yang, H.; Carter, R. G. J. Org. Chem. 2010, 75, 4929-4938
30. For a review of lycopodine syntheses, see: Hudlický?, T.; Reed, J. W. The Way of Synthesis; Wiley-VCH: Weinheim, 2007; pp 573-602.
31. Wenkert, E.; Broka, C. A. J. Chem. Soc., Chem. Commun. 1984, 714-715
32. Evans, D. A.; Scheerer, J. R. Angew. Chem., Int. Ed. 2005, 44, 6038-6042
33. Laemmerhold, K. M.; Breit, B. Angew. Chem., Int. Ed. 2010, 49, 2367-2370
34. Nakahara, K.; Hirano, K.; Maehata, R.; Kita, Y.; Fujioka, H. Org. Lett. 2011, 13, 2015-2017
35. Valenta, Z.; Deslongchamps, P.; Ellison, R. A.; Wiesner, K. J. J. Am. Chem. Soc. 1964, 86, 2533-2534
36. Dugas, H.; Ellison, R. A.; Valenta, Z.; Wiesner, K.; Wong, C. M. Tetrahedron Lett. 1965, 1279-1286
37. Dugas, H.; Hazenberg, M. E.; Valenta, Z.; Wiesner, K. Tetrahedron Lett. 1967, 4931-4936
38. Wiesner, K.; Musil, V.; Wiesner, K. J. Tetrahedron Lett. 1968, 5643-5646
39. A portion of this work was published in preliminary form: Lin, H.-Y.; Snider, B. B. Org. Lett. 2011, 13, 1234-1237
40. Reinshagen, H. Angew. Chem. 1964, 76, 994
41. Rohloff, J. C.; Dyson, N. H.; Gardner, J. O.; Alfredson, T. V.; Sparacino, M. L.; Robinson, J., III J. Org. Chem. 1993, 58, 1935-1938
42. Zhao, Y.; Zhao, J.; Zhou, Y.; Lei, Z.; Li, L.; Zhang, H. New J. Chem. 2005, 29, 769-772
43. Li, W.-D. Z.; Wang, Y.-Q. Org. Lett. 2003, 5, 2931-2934
44. Berry, M. B.; Craig, D.; Jones, P. S.; Rowlands, G. J. Beilstein J. Org. Chem. 2007, 3 (39).
45. Rodini, D. J.; Snider, B. B. Tetrahedron Lett. 1980, 21, 3857-3860
46. Keirs, D.; Overton, K.; Thakker, K. J. Chem. Soc., Chem. Commun. 1990, 310-311
47. Harding, C. E.; King, S. L. J. Org. Chem. 1992, 57, 883-886
48. Wempe, M. F.; Grunwell, J. R. J. Org. Chem. 1995, 60, 2714-2720
49. Balog, A.; Geib, S. J.; Curran, D. P. J. Org. Chem. 1995, 60, 345-352
50. Rhee, J. U.; Krische, M. J. Org. Lett. 2005, 7, 2493-2495
51. Jin, T.; Yamamoto, Y. Org. Lett. 2007, 9, 5259-5262
52. Miranda, P. O.; Ramí?rez, M. A.; Martí?n, V. S.; Padró?n, J. I. Chem. - Eur. J. 2008, 14, 6260-6268
53. Chavre, S. N.; Choo, H.; Lee, J. K.; Pae, A. N.; Kim, Y.; Cho, Y. S. J. Org. Chem. 2008, 73, 7647-7471
54. Lee, P. H.; Kim, H.; Lee, K.; Seomoon, D; Kim, S; Kim, H; Kim, H; Lee, M.; Shim, E; Lee, S; Kim, M; Han, M; Noh, K; Sridhar, M. Bull. Korean Chem. Soc. 2004, 25, 1687-1691
55. House, H. O.; Kleschick, W. A.; Zaiko, E. J. J. Org. Chem. 1978, 43, 3653-3661
56. House, H. O.; Sieloff, R. F.; Lee, T. V.; DeTar, M. B. J. Org. Chem. 1980, 45, 1800-1806
57. Campbell, K. A.; House, H. O.; Surber, B. W.; Trahanovsky, W. S. J. Org. Chem. 1987, 52, 2474-2481
58. álvarez-Pérez, M.; Marco-Contelles, J. ARKIVOC 2011, ii) 283-296
59. Jackson, A. C.; Goldman, B. E.; Snider, B. B. J. Org. Chem. 1984, 49, 3988-3994
60. 2AlCl, see: Fried, J.; Sih, J. C. Tetrahedron Lett. 1973, 3899-3902
61. Tanabe, Y. Bull. Chem. Soc. Jpn. 1994, 67, 3309-3313
62. Kim, Y.-H.; Lee, K. Y.; Oh, C.-Y.; Yang, J.-G.; Ham, W.-H. Tetrahedron Lett. 2002, 43, 837-841
63. Thompson, C. M.; Quinn, C. A.; Hergenrother, P. J. J. Med. Chem. 2009, 52, 117-125
64. Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. Int. Cong. Ser. (Stereosel. Synth. Nat. Prod.) 1979, 457, 71-82
65. Chem Abstr. 1980, 90, 76749.
66. Warnhoff, E. W.; Reynolds-Warnhoff, R. J. Org. Chem. 1963, 28, 1431-1433
67. Koenig, J.-J.; de Rostolan, J.; Bourbier, J.-C.; Jarreau, F.-X. Tetrahedron Lett. 1978, 2779-2782
68. Gó?mez-Sánchez, A.; Paredes-Leó?n, R.; Cámpora J. Magn. Reson. Chem. 1998, 36, 154-162
69. Voskressensky, L. G.; Borisova, T. N.; Listratova, A. V.; Kulikova, L. N.; Titov, A. A.; Varlamov, A. V. Tetrahedron Lett. 2006, 47, 4585-4589
70. Selig, P.; Herdtweck, E.; Bach, T. Chem. - Eur. J. 2009, 15, 3509-3525
71. Narasaka, K.; Morikawa, A.; Saigo, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 2773-2776
72. Yamada, K.; Kato, K.; Nagase, H.; Hirata, Y. Tetrahedron Lett. 1976, 65-66
73. Pojer, P. M.; Angyal, S. J. Aust. J. Chem. 1978, 31, 1031-1040
74. Nakamura, Y.; Burke, A. M.; Kotani, S.; Ziller, J. W.; Rychnovsky, S. D. Org. Lett. 2010, 12, 72-75
75. Nugent, W. A. Org. Lett. 2002, 4, 2133-2136
76. Mikolajczyk, M; Grzejszczak, S; Zatorski, A. J. Org. Chem. 1975, 40, 1979-1984
77. Kojima, T.; Fujisawa, T. Chem. Lett. 1978, 7, 1425-1426
78. Jones, A. B. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Ley, S. V., Eds.; Pergamon: Oxford, 1991; Vol. 7, pp 151-191.
79. Chen, B.-C.; Zhou, P.; Davis, F. A.; Ciganek, E. In Organic Reactions; Overman, L. E., Ed.; John Wiley & Sons, Inc.: New York, 2003; Vol. 62, pp 1-356.
80. Demir, A. S.; Sayrac, T.; Watt, D. S. Synthesis 1990, 1119-1121
81. Demir, A. S.; Emrullahoglu, M. Curr. Org. Synth. 2007, 4, 321-350
82. Bohlmann, F.; Mayer-Mader, R. Tetrahedron Lett. 1965, 171-172
83. Bailey, E. J.; Barton, D. H. R.; Elks, J.; Templeton, J. F. J. Chem. Soc. 1962, 1578-1591
84. Gersmann, H. R.; Bickel, A. F. J. Chem. Soc. B 1971, 2231-2237
85. Frimer, A. A.; Gilinsky-Sharon, P.; Aljadeff, G.; Gottlieb, H. E.; Hameiri-Buch, J.; Marks, V.; Philosof, R.; Rosental, Z. J. Org. Chem. 1989, 54, 4853-4866
86. Crowshaw, K.; Newstead, R. C.; Rogers, N. A. J. Tetrahedron Lett. 1964, 2307-2311
87. Jefford, C. W.; Rimbault, C. G. J. Am. Chem. Soc. 1978, 100, 6437-6445
88. Zhang, Z.; Foote, C. S. J. Org. Chem. 1993, 58, 5524-5527
89. Torii, S.; Inokuchi, T.; Kondo, K. J. Org. Chem. 1985, 50, 4980-4982
90. Doctor, B. P.; Toker, L.; Roth, E.; Silman, I. Anal. Biochem. 1987, 166, 399-403
91. Gordon, R. K.; Haigh, J. R.; Garcia, G. E.; Feaster, S. R.; Riel, M. A.; Lenz, D. E.; Aisen, P. S.; Doctor, B. P. Chem. Biol. Interact. 2005, 157â€"158, 239-246