Facile access to labdane-type diterpenes: Synthesis of coronarin C, zerumin B, labda-8(17), 13(14)-dien-15,16-olide and derivatives from (+)-manool

Journal of Chemical Research

Volumn , Issue 6, 2007, Pages 342-346

  Villamizar, José E ^a   Juncosa, José ^b   Pittelaud, Jean ^b   Hernández, Madeleyn ^b   Canudas, Nieves ^b   Tropper, Eleonora ^a   Salazar, Franklin ^a   Fuentes, Juan ^b  

^a INSTITUTO VENEZOLANO DE INVESTIGACIONES CIENTÍFICAS   (Venezuela)

^b UNIVERSIDAD SIMÓN BOLÍVAR   (Venezuela)

Author keywords

Coronarin C; Diterpene; Ent labdanes; Labdane type diterpenes; Zerumin B

Indexed keywords

EID: 34547768082     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/030823407X225527     Document Type: Article

References (25)

1. J.R. Hanson, Nat. Prod. Rep., 2000, 17, 165;
2. J.R. Hanson, Nat. Prod. Rep., 1999, 16, 209.
3. H. Itokawa, H. Morita, Planta Med., 1988, 54, 117;
4. K. Dimas, C. Demetzos, M. Marsellos, R. Sotiriadou, M. Malamas and D. Kokkinopoulos, (1998). Planta Med., 64, 208.
5. H. Itokawa, H. Morita, T. Katou, K. Takeya, A.J. Cavalheiro, R.C.B, de Oliveira, M. Ishige and M. Motidome, Planta Med., 1988, 54, 311.
6. H. Matsuda, T. Morikawa, Y. Sakamoto, I. Toguchida and M. Yoshikawa, Heterocycles, 2002, 56, 45;
7. T. Morikawa, H. Matsuda, Y. Sakamoto, K. Ueda, I. Toguchida and M. Yoshikawa Chem. Pharm. Bull., 2002, 50, 1045.
8. H.-X Xu, H. Dong and K.-Y Sim, Phytochemistry, 1996,42, 149.
9. F. Abas, N.H. Lajis, K. Shaari, D.A. Israf, J. Stanslas, U.K. Yusuf and S.M. Raof, J. Nat. Prod., 2005, 68, 1090.
10. C. Zdero, F. Bohlmann and R.M. King, Phytochemistry, 1992, 31, 1631.
11. (a) E. Scio, A. Ribeiro, T.M.A. Alves, A.J. Romahna, J.D. de S. Filho, G. Cordell and C.L. Zani, Phytochemistry, 2003, 64, 1125
12. (b) M.C. de Ia Torre, I. Garcia and M.A. Sierra, J. Nat. Prod., 2002, 65, 661.
13. M. Jung, I. Ko and S. Lee J. Nat. Prod., 1998, 61, 1394;
14. M. Jung, I. Ko, S. Lee, S.J. Choi, B.H. Youn and S.K. Kim, Bio. Med. Chem. Lett., 1988, 8, 3295;
15. M. Müller; J. Schröder; Ch. Magg and K. Seifert, Tetrahedron Lett., 1998, 39, 4655.
16. J. Boukouvalas, J-X Wang, O Marion and B. Nazi, J. Org. Chem., 2006, 71, 6670.
17. T. Nakano, A. Martin and A. Rojas, Tetrahedron, 1982, 38, 1217.
18. J. Villamizar, J. Fuentes, F. Salazar, E. Tropper and R. Alonso, J. Nat. Prod., 2003, 66, 1623 and refs cited therein;
19. J. Villamizar, F. Salazar, J. Fuentes, E. Tropper and R. Alonso, J. Chem. Res., 2002, 504 and refs cited therein.
20. S.V. Ley, J. Norman, W. Griffith and S. Marsden, Synthesis, 1994, 639.
21. M. Fétizon, M. Golfier and J-M. Louis, Tetrahedron, 1969,31, 171.
22. M.R. Kernan and D.J. Faulkner, J. Org. Chem., 1988, 53, 2773;
23. B.L. Feringa, Reel. Trav. Chim. Pays-Bas, 1987, 106, 469.
24. J.A. Turner and W. Herz, J. Org. Chem., 1977, 42, 1900;
25. P.M. Giang, P.T. Son and Otsuka H., Nat. Med., 2004, 58, 230.