Stereoselective synthesis of benzoquinolizidines and related homologues via intramolecular addition to dihydropyridones

Tetrahedron

Volumn 72, Issue 22, 2016, Pages 3032-3039

  Szcześniak, Piotr ^a   Ulikowski, Artur ^a   Staszewska Krajewska, Olga ^a   Lipner, Grzegorz ^a   Furman, Bartłomiej ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

Alkaloids; Anionic cyclizations; Benzoquinolizidines; Dihydropyridones; Lithium halogen exchange; Radical cyclization

Indexed keywords

2,3 DIHYDRO 4 PYRIDONE DERIVATIVE; 4 PYRIDONE DERIVATIVE; ALKALOID; BENZOQUINOLIZIDINE DERIVATIVE; DIHYDROPYRIDONE DERIVATIVE; FREE RADICAL; HALOGEN; LITHIUM; LITHIUM DERIVATIVE; PYRIDONE DERIVATIVE; QUINOLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATE; CYCLIZATION; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 84964320215     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2016.04.022     Document Type: Article

References (58)

1. A. Itoh, Y. Ikuta, Y. Baba, N. Tanahashi, and N. Nagakura Phytochemistry 52 1999 1169
2. O. Hesse Justus Liebigs Ann. Chem. 405 1914 28
3. M.T. Gonzales-Garza, S.A. Martlin, B.D. Mata-Cardena, and S. Said- Fernandez J. Pharm. Pharmacol. 45 1993 144
4. Y.F. Liou, I.H. Hall, and K.H. Lee J. Pharm. Sci. 71 1982 745
5. A. Itoh, Y. Ikuta, T. Tanahashi, and N. Nagakura J. Nat. Prod. 63 2000 723
6. A. Ito, Y.-H. Lee, H.-B. Chai, M.P. Gupta, N.R. Farnsforth, G.A. Gordell, J.M. Pezzuto, and A.D. Kinghorn J. Nat. Prod. 62 1999 1346
7. A.D. Kinghorn, N.R. Farnsworth, D.D. Soejarto, G.A. Cordell, J.M. Pezzuto, G.O. Udeani, M.C. Wani, M.E. Wall, H.A. Navarro, R.A. Kramer, A.T. Menendez, C.R. Fairchild, K.E. Lane, S. Forenza, D.M. Vyas, K.S. Lam, and Y.-Z. Shu Pure Appl. Chem. 71 1999 1611
8. I. Marin, J.P. Abad, J.P. Urena, and R. Amils Biochemistry 34 1995 16519
9. G.T. Tan, J.M. Pezzuto, A.D. Kinghorn, and S.H. Hughes J. Nat. Prod. 54 1991 143
10. A. Brossi, H. Lindlar, M. Walter, and O. Schnider Helv. Chim. Acta 41 1958 119
11. E.T. McNeal, G.A. Lewandowski, J.W. Daly, and C.R. Creveling J. Med. Chem. 28 1985 381
12. Q. Yu, W. Luo, J. Deschamps, H.W. Holloway, T. Kopajtic, J.L. Katz, A. Brossi, and N.H. Greig ACS Med. Chem. Lett. 1 2010 105
13. R. Perumal Samy, and P. Gopalakrishnakone Evid. Based Complement. Altern. Med. 7 2010 283
14. K. Orito, Y. Satoh, H. Nishizawa, R. Harada, and M. Tokuda Org. Lett. 2 2000 2535
15. T. Itoh, M. Miyazaki, H. Fukuoka, K. Nagata, and A. Ohsawa Org. Lett. 8 2006 1295
16. M.J. Rishel, K.K.D. Amarasinghe, S.R. Dinn, and B.F. Johnson J. Org. Chem. 74 2009 4001
17. M. Johannes, and K.-H. Altmann Org. Lett. 14 2012 3752
18. S. Lin, L. Deiana, A. Tseggai, and A. Córdova Eur. J. Org. Chem. 2012 398
19. M. Liu, and M.P. Sibi Tetrahedron 58 2002 7991
20. J.L. Vicario, D. Badía, L. Carrillo, J. Etxebarria, E. Reyes, and N. Ruiz Org. Prep. Proced. Int. 37 2005 513
21. L.-W. Xu, and C.-G. Xia Eur. J. Org. Chem. 2005 633
22. J.L. Vicario, D. Badía, and L. Carrillo Synthesis 2007 2065
23. D. Enders, C. Wang, and J.X. Liebich Chem. - Eur. J. 15 2009 11058
24. P.R. Krishna, A. Sreeshailam, and R. Srinivas Tetrahedron 65 2009 9657
25. S. Fustero, M. Sánchez-Roselló, and C. del Pozo Pure Appl. Chem. 82 2010 669
26. J. Wang, P. Li, P.Y. Choy, A.S.C. Chan, and F.Y. Kwong ChemCatChem 4 2012 917
27. Z. Amara, J. Caron, and D. Joseph Nat. Prod. Rep. 30 2013 1211
28. S. Fustero, D. Jiménez, J. Moscardó, S. Catalán, and C. del Pozo Org. Lett. 9 2007 5283
29. E.C. Carlson, L.K. Rathbone, H. Yang, N.D. Collett, and R.G.J. Carter Org. Chem. 73 2008 5155
30. S. Fustero, J. Moscardó, D. Jiménez, M.D. Pérez-Carrión, M. Sánchez-Roselló, and C. del Pozo Chem. - Eur. J. 14 2008 9868
31. Q. Cai, C. Zheng, and S.-L. You Angew. Chem., Int. Ed. 49 2010 8666
32. S. Fustero, C. del Pozo, C. Mulet, R. Lazaro, and M. Sánchez-Roselló Chem. - Eur. J. 17 2011 14267
33. Q. Gu, and S. You Chem. Sci. 2 2011 1519
34. J.-D. Liu, Y.-C. Chen, G.-B. Zhang, Z.-Q. Li, P. Chen, J.-Y. Du, Y.-Q. Tu, and C.-A. Fan Adv. Synth. Catal. 353 2011 2721
35. R. Miyaji, K. Asano, and S. Matsubara Org. Lett. 15 2013 3658
36. S. Fustero, J. Moscardó, M. Sánchez-Roselló, E. Rodríguez, and P. Barrio Org. Lett. 12 2010 5494
37. S. Fustero, E. Rodríguez, L. Herrera, A. Asensio, M.A. Maestro, and P. Barrio Org. Lett. 13 2011 6564
38. S. Fustero, L. Herrera, R. Lázaro, E. Rodríguez, M.A. Maestro, N. Mateu, and P. Barrio Chem. - Eur. J. 19 2013 11776
39. J. Guo, X. Sun, and S. Yu Org. Biomol. Chem. 12 2014 265
40. L.F. Tietze Chem. Rev. 96 1996 115
41. L.F. Tietze, and A. Modi Med. Res. Rev. 20 2000 304
42. S.F. Mayer, W. Kroutil, and K. Faber Chem. Soc. Rev. 30 2001 332
43. D. Enders, C. Grondal, and M.R.M. Hüttl Angew. Chem., Int. Ed. 46 2007 1570
44. A. Grossmann, and D. Enders Angew. Chem., Int. Ed. 51 2012 314
45. H. Pellissier Adv. Synth. Catal. 354 2012 237
46. D.L. Comins, and S.P. Joseph C.J. Moody, Advances in Nitrogen Heterocycles Vol. 2 1996 JAI, lnc. Greenwich, CT 251 294
47. M. Sato, S. Aoyagi, S. Yago, and C. Kibayashi Tetrahedron Lett. 37 1996 9063
48. B. Furman, and M. Dziedzic Tetrahedron Lett. 44 2003 6629
49. B. Furman, J. Frelek, M. Dziedzic, and A. Kamińska Pol. J. Chem. 12 2005 1123
50. M. Dziedzic, G. Lipner, J.M. Illangua, and B. Furman Tetrahedron 61 2005 8641
51. G. Lipner, and B. Furman Tetrahedron 64 2008 3464
52. S. Danishefsky, and T. Kitahara J. Am. Chem. Soc. 96 1974 7807
53. K. Ito, and H. Tanaka Chem. Pharm. Bull. 22 1974 2108
54. G. Satyanarayana, and M.E. Maier Tetrahedron 68 2012 1745
55. L. Castedo, J.C. Estevez, and L.J. Estevez Tetrahedron Lett. 33 1992 6883
56. W.E. Parham, and C.K. Bradsher Acc. Chem. Res. 15 1982 300
57. H. Ishibashi Tetrahedron 56 2000 1469
58. P.A. Grieco, M.D. Kaufman, J.F. Daeuble, and N. Saito J. Am. Chem. Soc. 118 1996 2095