The preparation of a 10-membered ring macrolactone by selective ozonolysis and the role of the dihydropyran-substituent on the MCPBA-oxidation reaction profile of β-lapachone phenazines

Journal of the Brazilian Chemical Society

Volumn 16, Issue 5, 2005, Pages 1074-1077

  Silva, Raphael S F ^a   Guimarães, Tiago T ^a   Teixeira, Daniel V ^a   Lobato, Ana Paula G ^a   Pinto, Maria Do Carmo F R ^a   De Simone, Carlos Alberto ^b   Soares, Janaína G ^b   Cioletti, Alessandra G ^b   Goulart, Marilia O F ^b   Pinto, Antonio V ^a  

^a FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b FEDERAL UNIVERSITY OF ALAGOAS   (Brazil)

Author keywords

10 membered ring macrolide; Effect of substituent; Ozonolysis; Selectivity; lapachone

Indexed keywords

EID: 30744460380     PISSN: 01035053     EISSN: 01035053     Source Type: Journal    
DOI: 10.1590/S0103-50532005000600027     Document Type: Article

References (26)

1. Emoto, T.; Kubosaki, N.; Yamagiwa, Y.; Kamikawa, T. A.; Tetrahedron Lett. 2000, 41, 355.
2. Abken, H-J.; Tietze, M.; Brodersen, J.; Bäumer, S.; Beifuss, U.; Deppenmeier, U.; J. Bacteriol. 1998, 2027.
3. Makgatho, M. E.; Anderson, R.; O'Sullivan, J. F.; Egan, T. J.; Freese, J. A.; Cornelius, N.; van Rensburg, C. E. J.; Drug Develop. Res. 2000, 50, 195.
4. Andrade-Neto, V.; Goulart, M.O. F. ; da Silva Fo., J.; da Silva, M.; Pinto, M.C.F.R.; Pinto, A. V.; Zalis, M. V.; Carvalho, L.; Krettli, A. U.; Bioorg. Med. Chem. Lett. 2004, 14 , 1145.
5. Neves-Pinto, C.; Malta, V.; Pinto, M.; Santos, R.; Castro, S.; Pinto, A.; J. Med. Chem. 2002, 45, 740.
6. Wang, W. Y.; Preville, P.; Morin, N.; Mounir, S.; Cai, W. Z.; Siddiqui, M. A.; Bioorg. Med. Chem. Lett. 2000, 10, 1151.
7. Rewcastle, G. W.; Denny, W. A.; Baguley, B. C.; J. Med. Chem. 1987, 30, 843.
8. Wang, S.; Miller, W.; Milton, J.; Vicker, N.; Stewart, A.; Charlton, P.; Mistry, P.; Hardick, D.; Denny, W.; Bioorg. Med. Chem. Med. Lett. 2002, 12, 415.
9. Goulart, M. O. F.; Cioletti, A. G.; Filho, J. D. S.; De Simone, C. A.; Castellano, E. E.; Emery, F. S.; De Moura, K. C. G.; Pinto, M. C. F. R.; Pinto, A. V.; Tetrahedron Lett. 2003, 44, 3581.
10. Labro, M. In Macrolide Antibiotics; Schoenfeld, W.; Kirst H., eds., Birkhaeuser Verlag: Basel, 2002,p. 37-52.
11. Jansen, R.; Kunze, B.; Reinchenbach, H.; Höfle, G.; Eur. J. Org. Chem. 2000, 903.
12. Kuczkowski, R. L.; Chem. Soc. Rev. 1992, 21, 79.
13. Kuczkowski, R. L.; Adv. Oxygenated Proc. 1991, 3, 1.
14. Fehr, C.; Galindo, J.; Farris, I.; Cuenca, A.; Helv. Chim. Acta 2004, 87, 1737.
15. Pryor, W.A.; Giamalva, D.; Church, D. F.; J. Am. Chem. Soc. 1985, 107, 2793.
16. Moriconi, E. J.; Salce, L.; Taranko, L. B.; J. Org. Chem. 1964, 29, 3297.
17. Bailey, P. S.; Erickson, R. E.; Org. Syn. 1961, 41, 41.
18. Shive, W.; Ballweber, E. G.; Ackermann, W. W.; J. Am. Chem. Soc. 1946, 68, 2144.
19. Borowitz, I. J.; Rapp, R. D.; J. Org. Chem. 1969, 34, 1370.
20. Molkentin, J.; Goepfert, A.; Tochtermanm, W.; Chem. Berich. 1991, 124, 1875.
21. Yamanaka, M.; Suda, S.; Yoneda, N.; Ohhara, W.; Chem. Pharm. Bull. 1992, 49, 666.
22. Kashima, C.; Takahashi, K.; Hosomi, A.; Heterocycles 1994, 37, 1075.
23. Supplementary Information: Supplementary crystallographic data have been deposited at the Cambridge Crystallographic Data Centre No. CCDC 257479. Copies of the data can be obtained, free of charge via www.ccdc.cam.ac.uk/conts/ retrieving.html (or from Cambridge Crystallographic Data Centre, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44-1223-336-033 or e-mail: deposit@ccdc.cam.ac.uk)
24. The International Union of Crystallography, International Tables for X-ray Crystallography, The Kynoch Press: Birmingham, England, 1962, vol. III, 275.
25. Pinto, C. N.; de Moura, K. C. G.; Emery, F. S.; Pinto, M. C. F. R.; Castro, S. L.; Dantas, A. P.; Poloquevich, P. F.; Pinto, A. V.; Arzneim-Forsch. 2000, 50, 1120.
26. Goulart, M. O. F.; Reys, J. R. M.; Emery, F. S.; Pinto, A. V.; Souza Filho, J. D.; Magnetic Res. Chem. 2004, 42, 663.