Synthesis of (-)-hygrine, (-)-norhygrine, (-)-pseudohygroline and (-)-hygroline via Nef reaction

Tetrahedron Letters

Volumn 52, Issue 49, 2011, Pages 6566-6568

  Bhat, Chinmay ^a   Tilve, Santosh G ^a  

^a GOA UNIVERSITY   (India)

Author keywords

Diastereoselective; Henry reaction; Nef reaction; Sedum alkaloid; Tropane alkaloid

Indexed keywords

HYGRINE; HYGROLINE; NORHYGRINE; PSEUDOHYGROLINE; TROPANE ALKALOID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; HENRY AND NEF REACTION;

SEDUM;

EID: 80555150528     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.09.118     Document Type: Article

References (60)

1. G. Cignarella, C.G. Gallo, and E. Testa J. Am. Chem. Soc. 83 1961 4999 5003
2. R. Noyori, Y. Baba, and H. Hayakawa J. Am. Chem. Soc. 96 1974 3336 3338
3. G. Forder, and R. Dharanipragada Nat. Prod. Rep. 1993 199 206
4. M. Majewski, and R. Lazny J. Org. Chem. 60 1995 5825 5830
5. M. Jordan, M. Human, S. Bieri, C. Christen, E. Poblete, and O. Munoz Phytochemistry 67 2006 570 578
6. T. Yamauchi, S. Hagiwara, and K. Higashiya J. Org. Chem. 73 2008 9784 9787
7. G.M. Sandala, D.M. Smith, and L. Radom J. Am. Chem. Soc. 130 2008 10684 10690
8. F.A. Davis, N. Theddu, and P.M. Gaspari Org. Lett. 11 2009 1647 1650
9. J.H. Kim, H. t'Hart, and J.F. Stevens Phytochemistry 41 1996 1319
10. For a review see: R.W. Bates, and K. Sa-Ei Tetrahedron 58 2002 5957
11. B.A. McGaw, and J.G. Woolley Phytochemistry 17 1978 257 259
12. L. Witte, K. Mular, and H.A. Arfermann Planta Med. 53 1987 192 197
13. E. Leete Planta Med. 36 1979 97 112
14. A.J. Parr Plant Cell Rep. 11 1992 270 273
15. J.H. Kim, H.T. Hart, and J.F. Stevens Phytochemistry 41 1996 1319 1324
16. E.P. Lansky, and R.A. Newman J. Ethnopharmacol. 103 2006 311 318
17. J.-H. Lee, B.-S. Jeong, J.-M. Ku, S.-S. Jew, and H.-G. Park J. Org. Chem. 71 2006 6690 6692
18. T.F. Platonava, and A.D. Kuzovkov Med. Prom. SSSR 17 1963 19
19. J.S. Fitzgerald Aust. J. Chem. 18 1965 589
20. S.A. Martin, J. Rovirosa, V. Gambaro, and M. Castillo Phytochemistry 19 1980 2007
21. F. Sorm Coll. Czech CC 12 1947 245 250
22. F. Galinovsky, and H. Zuber Monatsh. Chem. 84 1953 798 808
23. T. Shono, Y. Matsumura, and K. Tsubata J. Am. Chem. Soc. 103 1981 1172 1176
24. T. Langeskiold, and M. Lounasmaa Heterocycles 29 1983 671 675
25. T. Nagasaka, H. Yamamoto, and H. Hayashi Heterocycles 29 1989 155 164
26. A. Sud, D. Sureshkumar, and M. Klussmann Chem. Commun. 2009 3169 3171
27. T. Ponpandian, and S. Muthusubramanian Tetrahedron Lett. 52 2011 1520 1522
28. E.B. Arévalo-Garcia, and J.C.Q. Colmenares Tetrahedron Lett. 49 2008 3995 3996
29. M.S. Majik, and S.G. Tilve Tetrahedron Lett. 51 2010 2900 2902
30. H. Takahata, M. Kubota, and T. Momose Tetrahedron: Asymmetry 8 1997 2801
31. D.W. Knight, and R. Salter Tetrahedron Lett. 40 1999 5915
32. S.-I. Murahashi, Y. Imada, M. Kohno, and T. Kawakami Synlett 1993 395
33. C. Louis, and C. Hootele Tetrahedron: Asymmetry 8 1997 109 131
34. C. Vanucci-Bacqué, S. Calvet-Vitale, M.C. Bellassoued, and G. Lhommet ARKIVOC 2007 148 161
35. G. Enierga, D.C.R. Hockless, P. Perlmutter, M. Rose, S. Sjoberg, and K. Wong Tetrahedron Lett. 39 1998 2813
36. S.G. Davies, A.M. Fletcher, P.M. Roberts, and A.D. Smith Tetrahedron 65 2009 10192
37. J.S. Yadav, G. Narasimhulu, N.M. Reddy, and B.V.S. Reddy Tetrahedron Lett. 51 2010 1574 1577
38. J.B. Shet, V. Desai, and S.G. Tilve Synthesis 11 2004 1859
39. M.S. Majik, J. Shet, S.G. Tilve, and P.S. Parameswaran Syntheis 2007 663 665
40. M.S. Majik, P.S. Parameswaran, and S.G. Tilve Helv. Chim. Acta 91 2008 1500 1504
41. M.S. Majik, P.S. Parameswaran, and S.G. Tilve J. Org. Chem. 74 2009 3591 3594
42. M.S. Majik, P.S. Parameswaran, and S.G. Tilve J. Org. Chem. 74 2009 6378 6381
43. R. Ballini, and G. Bosica Synthesis 1994 723 726
44. R. Ballini, and M. Petrini Tetrahedron 2004 1017 1047
45. R. Ballini, and M. Petrini ARKIVOC 2009 195 223
46. M. Aginagalde, T. Bello, C. Masdeu, Y. Vara, A. Arrieta, and F.P. Cossio J. Org. Chem. 75 2010 7435 7438
47. K. Irie, K. Aoe, T. Tanaka, and S. Saito J. Chem. Soc., Chem. Commun. 1985 633
48. T. Ibuka, and G.N. Chu Chem. Pharm. Bull. 34 1986 2380
49. K.T. Wanner, and A. Kaertner Heterocycles 26 1987 921
50. F. Driessens, and C. Hootelé Can. J. Chem. 69 1991 211
51. C. Herdeis, W.A. Held, A. Kirfel, and F. Schwabenaender Liebigs Ann. 1995 1295
52. I.J. McAlpine, and R.W. Armstrong Tetrahedron Lett. 41 2000 1849
53. M. Sugiura, H. Hagio, R. Hirabayashi, and S. Kobayashi J. Am. Chem. Soc. 123 2001 12510
54. M. Heydenreich, A. Koch, L. Lazar, I. Szatmari, R. Sillanpaa, E. Kleinpeter, and F. Fulop Tetrahedron 59 2003 1951
55. N.S. Josephsohn, M.L. Snapper, and A.H. Hoveyda J. Am. Chem. Soc. 126 2004 3734
56. C. Dooms, P. Laurent, D. Daloze, J. Pasteels, O. Nedved, and J.-C. Braekman Eur. J. Org. Chem. 2005 1378
57. V.B. Birman, H. Jiang, and X. Li Org. Lett. 9 2007 3237
58. A.E. Al-Sarabi, A. Bariau, M. Gabant, J.-C. Wypych, P. Chalard, and Y. Troin ARKIVOC 2007 119
59. L.-J. Chen, and D.-R. Hou Tetrahedron: Asymmetry 19 2008 715
60. S. Krishnan, J.T. Bagdanoff, D.C. Ebner, Y.K. Ramtohul, U.K. Tambar, and B.M. Stoltz J. Am. Chem. Soc. 130 2008 13745