Synthesis of (±)-7-hydroxylycopodine

Organic Letters

Volumn 13, Issue 5, 2011, Pages 1234-1237

  Lin, Hong Yu ^a   Snider, Barry B ^a  

^a BRANDEIS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 HYDROXYLYCOPODINE; 7-HYDROXYLYCOPODINE; ALKALOID; CLAVOLONINE; LYCOPODINE; QUINOLIZINE DERIVATIVE; SAUROINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; HUPERZIA; STEREOISOMERISM; SYNTHESIS;

ALKALOIDS; CYCLIZATION; HUPERZIA; MODELS, MOLECULAR; MOLECULAR STRUCTURE; QUINOLIZINES; STEREOISOMERISM;

EID: 79952120235     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200119h     Document Type: Article

References (52)

1. Ortega, M. G.; Agnese, A M.; Cabrera, J. L. Tetrahedron Lett. 2004, 45, 7003-7005
2. 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.
3. For recent reviews on lycopodium alkaloids, see: Kobayashi, J.; Morita, H. In The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Elsevier: San Diego, CA, 2005; Vol. 61, pp 1 -57.
4. Ma, X.; Gang, D. R. Nat. Prod. Rep. 2004, 21, 752-772
5. Hirasawa, Y.; Kobayashi, J.; Morita, H. Heterocycles 2009, 77, 679-729
6. For recent reviews on huperzine A for treatment of Alzheimer's disease, see: Hostettmann, K.; Borloz, A.; Urbain, A.; Marston, A. Curr. Org. Chem. 2006, 10, 825-847
7. 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.
8. Bai, D. Pure Appl. Chem. 2007, 79, 469-479
9. Little, J. T.; Walsh, S.; Aisen, P. S. Exp. Opin. Invest. Drugs 2008, 17, 209-215
10. Desilets, A. R.; Gickas, J. J.; Dunican, K. C. Ann. Pharmacother. 2009, 43, 514-518
11. Stork, G.; Kretchmer, R. A.; Schlessinger, R. H. J. Am. Chem. Soc. 1968, 90, 1647-1648
12. Ayer, W. A.; Bowman, W. R.; Joseph, T. C.; Smith, P. J. Am. Chem. Soc. 1968, 90, 1648-1650
13. Kim, S.; Bando, Y.; Horii, Z. Tetrahedron Lett. 1978, 2293-2294
14. Heathcock, C. H.; Kleinman, E. F.; Binkley, E. S. J. Am. Chem. Soc. 1982, 104, 1054-1068
15. Schumann, D.; Müller, H.-J.; Naumann, A. Liebigs Ann. Chem. 1982, 1700-1705
16. Kraus, G. A.; Hon, Y. S. J. Am. Chem. Soc. 1985, 107, 4341-4342
17. Heterocycles 1987, 25, 377-386.
18. Padwa, A.; Brodney, M. A.; Marino, J. P.; Sheehan, S. M. J. Org. Chem. 1997, 62, 78-87
19. Greico, P. A.; Dai, Y. J. J. Am. Chem. Soc. 1998, 120, 5128-5129
20. Mori, M.; Hori, K.; Akashi, M.; Hori, M.; Sato, Y.; Nishida, M. Angew. Chem., Int. Ed. 1998, 37, 636-637
21. Yang, H.; Carter, R. G.; Zakharov, L. N. J. Am. Chem. Soc. 2008, 130, 9238-9239
22. Yang, H.; Carter, R. G. J. Org. Chem. 2010, 75, 4929-4938
23. For a review of lycopodine syntheses, see: Hudlický, T.; Reed, J. W. The Way of Synthesis; Wiley-VCH: Weinheim, 2007; pp 573 -602.
24. Wenkert, E.; Broka, C. A. J. Chem. Soc., Chem. Commun. 1984, 714-715
25. Evans, D. A.; Scheerer, J. R. Angew. Chem., Int. Ed. 2005, 44, 6038-6042
26. Laemmerhold, K. M.; Breit, B. Angew. Chem., Int. Ed. 2010, 49, 2367-2370
27. Tan, C.-H. Ph. D. Thesis, Shanghai Institute of Materia Medica, 2001.
28. Tan, C.-H.; Zhu, D.-Y. Helv. Chim. Acta 2004, 87, 1963-1967
29. Valenta, Z.; Deslongchamps, P.; Ellison, R. A.; Wiesner, K. J. J. Am. Chem. Soc. 1964, 86, 2533-2534
30. Dugas, H.; Ellison, R. A.; Valenta, Z.; Wiesner, K.; Wong, C. M. Tetrahedron Lett. 1965, 1279-1286
31. Dugas, H.; Hazenberg, M. E.; Valenta, Z.; Wiesner, K. Tetrahedron Lett. 1967, 4931-4936
32. Wiesner, K.; Musil, V.; Wiesner, K. J. Tetrahedron Lett. 1968, 5643-5646
33. Reinshagen, H. Angew. Chem. 1964, 76, 994
34. For the preparation of related vinylogous amides by this method, see: 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
35. Zhao, Y.; Zhao, J.; Zhou, Y.; Lei, Z.; Li, L.; Zhang, H. New J. Chem. 2005, 29, 769-772
36. For examples of Wacker oxidations in the presence of an amine, see: Li, W.-D.; Wang, Y.-Q. Org. Lett. 2003, 5, 2931-2934
37. Berry, M. B.; Craig, D.; Jones, P. S.; Rowlands, G. J. Beilstein J. Org. Chem. 2007, 3, no. 39.
38. For examples of Prins additions of ketones and aldehydes to alkynes, see: Rodini, D. J.; Snider, B. B. Tetrahedron Lett. 1980, 21, 3857-3860
39. Keirs, D.; Overton, K.; Thakker, K. J. Chem. Soc., Chem. Commun. 1990, 310-311
40. Harding, C. E.; King, S. L. J. Org. Chem. 1992, 57, 883-886
41. Wempe, M. F.; Grunwell, J. R. J. Org. Chem. 1995, 60, 2714-2720
42. Balog, A.; Geib, S. J.; Curran, D. P. J. Org. Chem. 1995, 60, 345-352
43. Rhee, J. U.; Krische, M. J. Org. Lett. 2005, 7, 2493-2495
44. Jin, T.; Yamamoto, Y. Org. Lett. 2007, 9, 5259-5262
45. Miranda, P. O.; Ramírez, M. A.; Martín, V. S.; Padrón, J. I. Chem.-Eur. J. 2008, 14, 6260-6268
46. Chavre, S. N.; Choo, H.; Lee, J. K.; Pae, A. N.; Kim, Y.; Cho, Y. S. J. Org. Chem. 2008, 73, 7647-7471
47. Thompson, C. M.; Quinn, C. A.; Hergenrother, P. J. J. Med. Chem. 2009, 52, 117-125
48. Warnhoff, E. W.; Reynolds-Warnhoff, R. J. Org. Chem. 1963, 28, 1431-1433
49. Koenig, J.-J.; de Rostolan, J.; Bourbier, J.-C.; Jarreau, F.-X. Tetrahedron Lett. 1978, 2779-2782
50. Narasaka, K.; Morikawa, A.; Saigo, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 2773-2776
51. Yamada, K.; Kato, K.; Nagase, H.; Hirata, Y. Tetrahedron Lett. 1976, 65-66
52. Pojer, P. M.; Angyal, S. J. Aust. J. Chem. 1978, 31, 1031-1040