Partial synthesis of C-ring derivatives from oleanolic and maslinic acids. Formation of several triene systems by chemical and photochemical isomerization processes

Tetrahedron

Volumn 60, Issue 7, 2004, Pages 1491-1503

  García Granados, Andrés ^a   López, Pilar E ^a   Melguizo, Enrique ^a   Parra, Andrés ^a   Simeó, Yolanda ^a  

^a UNIVERSITY OF GRANADA   (Spain)

Author keywords

Diene; Isomerization; Maslinic; Oleanolic; Triene; Triterpene

Indexed keywords

ALKADIENE; ERGOCALCIFEROL; ESTER DERIVATIVE; MASLINIC ACID; OLEANOLIC ACID; OLIVE OIL; STEROL DERIVATIVE; TACHYSTEROL; TRITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERIZATION; PHOTOCHEMISTRY; PRIORITY JOURNAL; SOLID WASTE; SYNTHESIS;

EID: 0742272065     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.12.023     Document Type: Article

References (23)

1. Dictionary of Natural Products on CD-ROM, Chapman and Hall, ISSN 0966-2146 ver. 5.1 (1996), oleanolic acid CAS (508-02-01), maslinic acid CAS (4373-41-5).
2. Garcia-Granados, A.; Martinez, A.; Parra, A.; Rivas, F. P.C.T. Int. Appl. W0 043331, 1998; (Chem. Abstr. 1998, 128, 179706).
3. Manna S., Yadagiri P., Falck. J. Chem. Soc., Chem. Commun. 1987;1324-1325.
4. Liu. J. Ethnopharmacol. 49:1995;57-68.
5. Garcia-Granados A., Dueñas J., Moliz J.N., Parra A., Perez F.L., Dobado J.A., Molina J. J. Chem. Res. (S). 2000;56-57.
6. Garcia-Granados A., Dueñas J., Moliz J.N., Parra A., Perez F.L., Dobado J.A., Molina J. J. Chem. Res. (M). 2:2000;0326-0339.
7. Garcia-Granados A., Dueñas J., Melguizo E., Moliz J.N., Parra A., Perez F.L., Dobado J.A., Molina J. J. Chem. Res. (S). 2000;212-213.
8. Garcia-Granados A., Dueñas J., Melguizo E., Moliz J.N., Parra A., Perez F.L., Dobado J.A., Molina J. J. Chem. Res. (M). 2:2000;0653-0670.
9. Rasmusson G.H., Reynolds G.F., Steinberg N.G., Walton E., Patel G.F., Liang T., Cascieri M.A., Cheung A.H., Brooks J.R., Berman C. J. Med. Chem. 29:1986;2298.
10. Spera G., Lubrano C. Int. J. Immunopathol. Pharmacol. 91:1996;33.
11. Ling Y.Z., Li J.S., Kato K., Liu Y., Wang X., Klus G.T., Marat K., Nnane I.P., Brodie A.M.H. Bioorg. Med. Chem. 6:1998;1683.
12. Garcia-Granados A., Lopez P.E., Melguizo E., Moliz J.N., Parra A., Simeo Y. J. Org. Chem. 68:2003;4833-4844.
13. Garcia-Granados A., Lopez P.E., Melguizo E., Parra A., Simeo Y. Tetrahedron Lett. 44:2003;6673-6677.
14. Monaco P., Caputo R., Palumbo G., Mangoni L. Phytochemistry. 12:1973;939.
15. Havinga E., de Kock R.J., Rappoldt M.P. Tetrahedron. 11:1960;276-284.
16. Lugtenburg J., Havinga E. Tetrahedron Lett. 28:1969;2391-2394.
17. Gottfried N., Kaiser W., Braun M., Fuss W., Kompa K.L. Chem. Phys. Lett. 110:1984;335-339.
18. Schönecker B., Reichenbächer M., Gliesing S., Gonschior M., Griebenow S., Scheddin D., Mayer H. Steroids. 63:1998;28-36.
19. Autrey R.L., Barton D.H.R., Ganguly A.K., Reusch W.H. J. Chem. Soc. 3:1961;3313-3319.
20. Misra L., Laatsch H. Phytochemistry. 54:2000;969-974.
21. Lampasona M.E.P., Catalan C.A.N., Gedris T.E., Herz W. Phytochemistry. 49:1998;2061-2064.
22. Agata I., Corey E.J., Hortmann A.G., Klein J., Proskow S., Ursprung J.J. J. Org. Chem. 30:1965;1698-1710.
23. Clayden J., Greeves N., Warren S., Wothers P. Organic Chemistry. Pericyclic reactions 2: sigmatropic and electrocyclic reactions. 2001;Oxford University Press, Oxford. Chapter 36.