Aldol condensations in pyrazino[2,1-b]quinazolines. Fast access to seco-ardeemin derivatives

Arkivoc

Volumn 2011, Issue 3, 2010, Pages 72-98

  Cledera, Pilar ^a   Villacampa, Mercedes ^a   Avendaño, Carmen ^a   Menéndez, J Carlos ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

1 b quinazolines; Aldol condensation; Benzene hydrogenation; Catalytic hydrogenation; Diastereoselectivity; Pyrazino 2

Indexed keywords

EID: 79953126615     PISSN: 1551-7012     EISSN: 15517004     Source Type: Journal    
DOI: 10.3998/ark.5550190.0012.307     Document Type: Article

References (37)

1. For reviews, see: (a) Mhaske, S. B.; Argade, N. P. Tetrahedron 2006, 62, 9787.
2. Eguchi, S. Top. Heterocycl. Chem. 2006, 6, 113.
3. For a review, see: Avendaño, C.; Menéndez, J. C. Curr. Org. Chem. 2003, 7, 149.
4. Penn, J.; Mantle, P. G.; Bilton, J. N.; Sheppard, R. N. J. Chem. Soc., Perkin Trans. 1 1992, 1495.
5. For the synthesis of both enantiomers of glyantripine, see: Cledera, P.; Avendaño, C.; Menéndez, J. C. J. Org. Chem. 2000, 65, 1743.
6. Numata, A.; Takahashi, C.; Matsushita, T.; Miyamoto, T.; Kawai, K.; Usami, Y.; Matsumura, E.; Inoue, M.; Ohishi, H.; Shingu, T. Tetrahedron Lett. 1992, 33, 1621.
7. Takahashi, C.; Matsushita, T.; Doi, M.; Minoura, K.; Shingu, T.; Kumeda, Y.; Numata A. J. Chem. Soc. Perkin Trans. 1 1995, 2345.
8. Wong, S.-M.; Musza, L. L.; Kydd, G. C.; Kullnig, R.; Gillum, A. M.; Cooper, R. J. Antibiotics 1993, 46, 545.
9. Fujimoto, H.; Negishi, E.; Yamaguchi, K.; Nishi, N.; Yamazaki, M. Chem. Pharm. Bull. 1996, 44, 1843.
10. Hochlowski, J. E., Mullally, M. M.; Spanton, S. G., Whittern, D. N.; Hill, P.; McAlpine, J. B., J. Antibiot. 1993, 46, 380.
11. For the synthesis of N-acetylardeemin, see: Depew, K. M.; Marsden, S. P.; Zatorska, D.; Zatorski, A.; Bornmann, W. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 11953.
12. Karwowski, J. P.; Jackson, M.; Rasmussen, R. R.; Humphrey, P. E.; Poddig, J. B.; Kohl, W. L.; Scherr, M. H.; Kadam, S.; McAlpine, J. B., J. Antibiot. 1993, 46, 374.
13. For reviews of MDR inhibitors, see: (a) Avendaño, C.; Menéndez, J. C. Curr. Med. Chem. 2002, 9, 159.
14. Avendaño, C.; Menéndez, J. C. Med. Chem. Rev. Online, 2004, 1, 419.
15. Chou, T. C.; Depew, K. M.; Zheng, Y. H.; Safer, M. L.; Chan, D.; Helfrich, B.; Zatorska, D.; Zatorski, A.; Bornmann, W.; Danishefsky, S. J. Proc. Natl. Acad. Sci. USA 1998, 95, 8369.
16. Méndez-Vidal, C.; Quesada, A. R. Cancer Lett. 1998, 132, 45.
17. Avendaño, C.; Caballero, E.; Méndez-Vidal, C.; Quesada, A. R.; Menéndez, J. C. Lett. Drug Des. Discov. 2006, 3, 369.
18. Chou, T.-C.; Bertino, J. R.; Danishefsky, S. J.; Kahan, B. D. U. S. Patent 6,355,639 (March 12, 2002).
19. Cledera, P.; Avendaño, C.; Menéndez, J. C. Tetrahedron 1998, 54, 12349.
20. Cledera, P.; Sánchez, J. D.; Caballero, E.; Yates, T.; Ramírez, E. G.; Avendaño, C.; Ramos, M. T.; Menéndez, J. C. Synthesis 2007, 3390.
21. Rajappa, S.; Advani, B. G. J. Chem. Soc., Perkin Trans. I 1974, 2122.
22. Martín-Santamaría, S.; Buenadicha, F. L.; Espada, M.; Söllhuber, M. M.; Avendaño, C. J. Org. Chem. 1997, 62, 6424.
23. Martín-Santamaría, S.; Espada, M.; Avendaño, C. Tetrahedron 1997, 53, 16795.
24. Heredia, M. L.; Fernández, M.; Cuesta, E.; Avendaño, C. Tetrahedron: Asymmetry 2001, 12, 411.
25. For one earlier, isolated example of this reaction, see: Heredia, M. L.; Cuesta, E.; Avendaño, C. Tetrahedron, 2001, 57, 1987.
26. For a review of the captodative effect in α-amino acids, see: Easton, C. J. Chem. Rev. 1997, 97, 53.
27. The source of oxygen must have been the argon used as "inert" atmospehere. For an account describing unexpected effects due to the presence of oxygen in a reaction carried out under an argon atmosphere, see: Scheiber, S. L.; Ragan, J. A.; Standaert, R. F., in Lindberg, T. (ed.) Strategies and Tactics in Organic Synthesis, vol. 3, chapter 11. Academic Press (San Diego), 1991.
28. Halliwell, B.; Gutteridge, J. M. C. Free Radicals in Biology and Medicine, 3rd Ed. p. 601. Oxford University Press, 1999.
29. Beak, P.; Brubaker, G. R.; Farney, R. F. J. Am. Chem. Soc., 1976, 98, 3621.
30. Wiberg, K. B.; Bailey, W. F. J. Org. Chem. 2002, 67, 5365.
31. Gallina, C.; Liberatori, A. Tetrahedron Lett, 1973, 14, 1135.
32. Gallina, C.; Liberatori, A. Tetrahedron, 1974, 30, 667.
33. However, a detailed study carried out by the Kobayashi group in the context of a total synthesis of neoechinulin A using chiral HPLC as the quantitation method showed a small degree of racemization for this type of reactions. See: Aoki, T. Kamisuki, S.; Kimoto, M.; Ohnishi, K.; Takakusagi, Y.; Kuramochi, K.; Takeda, Y.; Nakazaki, A.; Kuroiwa, K.; Ohuchi, T.; Sugawara, F.; Arai, T.; Kobayashi, S. Synlett 2006, 677.
34. Grahl-Nielsen, O. Tetrahedron Lett. 1969, 10, 2827.
35. There are two previous literature examples of the partial reduction of the benzene ring in pyrazino[2,1-b]quinazoline-3,6-diones, although in an acidic reaction medium. See: (a) Bartolomé, M. T.; Buenadicha, F. L.; Avendaño, C.; Söllhuber, M. Tetrahedron: Asymmetry 1998, 9, 249.
36. Buenadicha, F. L.; Bartolomé, M. T.; Aguirre, M. J.; Avendaño, C.; Söllhuber, M. M. Tetrahedron: Asymmetry 1998, 9, 483.
37. The 2-benzyl and 2-(4-methoxybenzyl) analogues of 4 are known in the literature, and showed similar optical rotation values to our compound (see reference 22b).