A new synthetic approach to 7-hydroxynitidine

Tetrahedron Letters

Volumn 49, Issue 36, 2008, Pages 5262-5264

  Ramani, Prasanna ^a   Fontana, Gabriele ^b  

^a UNIVERSITY OF MILAN   (Italy)

^b INDENA S P A   (Italy)

Author keywords

7 Hydroxynitidine; Benzo c phenanthridine alkaloids; Microwave irradiation; Radical cyclization

Indexed keywords

7 HYDROXYNITIDINE; BENZO[C]PHENANTHRIDINE DERIVATIVE; NITIDINE;

ARTICLE; CHEMICAL REACTION; CRYSTALLIZATION; CYCLIZATION; MICROWAVE IRRADIATION; PURIFICATION; SYNTHESIS;

EID: 47549109376     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.06.108     Document Type: Article

References (22)

1. Simanek V. In: Brossi A. (Ed). The Alkaloids Vol. 26 (1985), Academic Press, Orlando 185-240
2. Mackay S.P., et al. In: Katritzky A.R. (Ed). Advances in Heterocyclic Chemistry Vol. 67 (1997), Academic Press, New York 345-389
3. Ishikawa T., and Ishii H. Heterocycles 50 (1999) 627-639
4. Hwang J.K., Baek N.I., and Park J.H. Int. J. Antimicrob. Agents 23 (2004) 377-381
5. Eun J.P., and Koh G.Y. Biochem. Biophys. Res. Commun. 317 (2004) 618-624
6. Li D., Zhao B., Sim S.P., Li T.K., Liu A., Liu L.F., and LaVoie E.J. Bioorg. Med. Chem. 11 (2003) 521-528
7. Le T.N., Gang S.G., and Cho W.-J. Tetrahedron Lett. 45 (2004) 2763-2766
8. Geen G.R., Mann I.S., and Mullane M.V. Tetrahedron 54 (1998) 9875-9894
9. Le T.N., Gang S.G., and Cho W.-J. J. Org. Chem. 69 (2004) 2768-2772
10. Nakanishi T., and Suzuki M. Org. Lett. 1 (1999) 985-988
11. Nakanishi T., Suzuki M., Mashiba A., Ishikawa K., and Yokotsuka T. J. Org. Chem. 63 (1998) 4235-4239
12. Gross H., Rieche A., and Matthey G. Chem. Ber. 96 (1963) 308-313
13. Stermitz F.R., Gillespie J.P., Amoros L.G., Romero R., and Stermitz T.A. J. Med. Chem. 18 (1975) 708-713
14. Clark J.H., Holland H.L., and Miller J.M. Tetrahedron Lett. 41 (1976) 3361-3364
15. Billman J.H., and McDowell J.W. J. Org. Chem. 26 (1961) 1437-1440
16. + (Br isotope)).
17. 6) δ: 4.0 (s, 3H), 4.1 (s, 3H), 5.3 (s, 2H), 6.1 (s, 2H), 7.2 (s, 1H), 7.28-7.4 (m, 2H), 7.40-7.44 (m, 2H), 7.6 (m, 1H), 7.7 (m, 1H), 8.24 (d, 1H), 8.7 (s, 1H), 9.6 (s, 1H). MS m/z 440 (M+1).
18. http://www.biotage.com/DynPage.aspx?id=22017.
19. Kiprianov A.I., and Tolmachev A.I. Zh. Obshch. Khim. 29 (1959) 2868-2874
20. Chem. Abstr. 54 (1960) 12126
21. Simanek V., and Preininger V. Heterocycles 6 (1977) 475-497
22. Bunting J.W. Adv. Heterocycl. Chem. 25 (1979) 1-82