A non-enzymatic synthesis of (S)-(-)-rosmarinic acid and a study of a biomimetic route to (+)-rabdosiin

Canadian Journal of Chemistry

Volumn 75, Issue 12, 1997, Pages 1783-1794

  Bogucki, David E ^a   Charlton, James L ^a  

^a UNIVERSITY OF MANITOBA   (Canada)

Author keywords

Lignan; Oxidative coupling; Rabdosiin; Rosmarinic acid

Indexed keywords

DERIVATIVES; ESTERS; FREE RADICAL REACTIONS; OXIDATION; SYNTHESIS (CHEMICAL);

CAFFEIC ACID; DEALLYLATION; DIASTEREOMERS; DIHYDROXYPHENYL LACTIC ACID; FREE RADICAL COUPLING CYCLIZATION; LIGNAN; METHYL MANDELYL SINAPATE; RABDOSIIN; ROSMARINIC ACID; THOMASIDIOATE DIESTER;

CARBOXYLIC ACIDS;

CAFFEIC ACID DERIVATIVE; RABDOSIIN; ROSMARINIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG CONFORMATION; DRUG OXIDATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0031427199     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v97-612     Document Type: Article

References (52)

1. M.L. Scarpati and G. Oriente. Ric. Sci. 28, 2329 (1958).
2. M. Kuhnt, A. Pröbstle, H. Rimpler, R. Bauer, and M. Heinrich. Planta Med. 61, 227 (1995).
3. P.W. Peake, B.A. Pussell, P. Martyn, V. Timmermans, and J.A. Charlesworth. Int. J. Immunopharmacol. 13, 853 (1991).
4. W. Englberger, U. Hadding, E. Etschenberg, E. Graf, S. Leyck, J. Winkelmann, and M.J. Parnham. Int. J. Immunopharmacol. 10, 729 (1988).
5. Y. Kimura, H. Okuda, T. Okuda, T. Hatano, and S. Arichi. J. Nat. Prod. 50, 392 (1987).
6. M. Rampart, J.R. Beetens, H. Bult, A.G. Herman, M.J. Parnham, and J. Winkelmann. Biochem. Pharmacol. 35, 1397 (1986).
7. H. Bult, A.G. Herman, and M. Rampart. Br. J. Pharmacol. 84, 317 (1985).
8. L. Gracza, H. Koch, and E. Löffler. Arch. Pharm. 318, 1090 (1985).
9. K. Pabsch, M. Petersen, N.N. Rao, A.W. Alfermann, and C. Wandrey. Recl. Trav. Chim. Pays-Bas, 110, 199 (1991).
10. J.K.S. Nuytinck, R.J.A. Goris, E.S. Kalter, and P.H.M. Schillings. Agents Actions, 17, 373 (1985).
11. H. Kohda, O. Takeda, S. Tanaka, K. Yamasaki, A. Yamashita, T. Kurokawa, and S. Ishibashi. Chem. Pharm. Bull. 37, 1287 (1989).
12. J.L. Lamaison, C. Petitjean-Freytet, and A. Carnat. Pharm. Acta Helv. 66, 185 (1991).
13. J.L. Lamaison, C. Petitjean-Freytet, and A. Carnat. Ann. Pharm. Fr. 48, 103 (1990).
14. K.P.M. van Kessel, E.S. Kalter, and J. Verhoef. Agents Actions, 17, 375 (1985).
15. G.T. Liu, T.M. Zhang, B.E. Wang, and Y.W. Wang. Biochem. Pharmacol. 43. 147 (1992).
16. L.R. Simpol, H. Otsuka, K. Ohtani, R. Kasai, and K. Yamasaki. Phytochemistry, 36, 91 (1994).
17. N.Z. Alimkhodzhaeva and R.L. Khazanovich. Chem. Abstr. 82, 167491r (1975).
18. T.E. Van Dyke, L. Braswell, and S. Offenbacher. Agents Actions, 19, 376 (1986).
19. Z. Dimitrova, B. Dimov, N. Manolova, S. Pancheva, D. Ilieva, and S. Shishkov. Acta Microbiol. Bulg. 29, 65 (1993).
20. M. Auf'mkolk, J. Kohrle, H. Gumbinger, H. Winterhoff, and R.D. Hesch. Horm. Metab. Res. 16, 188 (1984).
21. A. Razzaque and B.E. Ellis. Planta, 137, 287 (1977).
22. M.H. Zenk, H. El-Shagi, and B. Ulbrich. Naturwissenschaften, 64, 585 (1977).
23. W. De-Eknamkul and B.E. Ellis. Planta Med. 50, 346 (1984).
24. W. De-Eknamkul and B.E. Ellis. Phytochemistry, 26, 1941 (1987).
25. W. De-Eknamkul and B.E. Ellis. Arch. Biochem. Biophys. 257, 430 (1987).
26. M. Petersen, E. Häusler, B. Karwatzki, and J. Meinhard. Planta, 189, 10 (1993).
27. B.E. Ellis and G.H.N. Towers. Biochem. J. 118, 291 (1970).
28. I. Agata, T. Hatano, S. Nishibe, and T. Okuda. Chem. Pharm. Bull. 36, 3223 (1988).
29. I. Agata, T. Hatano, S. Nishibe, and T. Okuda. Phytochemistry, 28, 2447-2450 (1989).
30. M. Nishizawa, M. Tsuda, and K. Hayashi. Phytochemistry, 29, 2645 (1990).
31. Y. Kashiwada, M. Nishizawa, T. Yamagishi, T. Tanaka, G. Nonaka, L.M. Cosentino, J.V. Snider, and K. Lee. J. Nat. Prod. 58, 392 (1995).
32. Y. Kashiwada, K.F. Bastow, and K. Lee. Bioorg. Med. Chem. Lett. 5, 905 (1995).
33. J.J.L. Cilliers and V.L. Singleton. J. Agric. Food Chem. 39, 1298 (1991).
34. A.F.A. Wallis. Aust. J. Chem. 26, 1571 (1973).
35. H. Setälä, A. Pajunen, I. Kipeläinen, and G. Brunow. J. Chem. Soc. Perkin Trans. 1, 1163 (1994).
36. J.L. Charlton, V.A. Sayeed, K. Koh, W.F. Lau, H.K. Lai, and A.R. Bell. J. Agric. Food Chem. 38, 1719 (1990).
37. J.A. Osborn, F.H. Jardine, J.F. Young, and G. Wilkinson. J. Chem. Soc. A: 1711 (1966).
38. R. Gigg. J. Chem. Soc. Perkin Trans. 1, 738 (1980).
39. D.L. Boger and D. Yohannes. J. Org. Chem. 52, 5283 (1987).
40. B. Wünsch and M. Zott. Liebigs Ann. Chem. 39 (1992).
41. N.N. Rao and H.J. Roth. Arch. Pharm. 321, 179 (1988).
42. J. Wang, H. He, Y. Zhu, D. Shi, Y. Li, and Y. Zhang. Chem. Abstr. 115, 120154t (1991).
43. J.A. Dale, D.L. Dull, and H.S. Mosher. J. Org. Chem. 34, 2543 (1969).
44. D.E. Ward and C.K. Rhee. Tetrahedron Lett. 32, 7165 (1991).
45. V. Dourtoglou, B. Gross, V. Lambropoulou, and C. Zioudrou. Synthesis, 572 (1984).
46. E.J. Corey, H. Cho, C. Rücker, and D.H. Hua. Tetrahedron Lett. 22, 3455 (1981).
47. M. Lalonde and T.H. Chan. Synthesis, 817 (1985).
48. F. Guibe and Y. Saint M'Leux. Tetrahedron Lett. 22, 3591 (1981).
49. E. Keinan and P.A. Gleize. Tetrahedron Lett. 23, 477 (1982).
50. P. Four and F. Guibe. Tetrahedron Lett. 23, 1825 (1982).
51. F. Guibe, O. Dangles, and G. Balavoine. Tetrahedron Lett. 27, 2365 (1986).
52. J.L. Charlton, G.L. Plourde, K. Koh, and A.S. Secco. Can. J. Chem. 68, 2022 (1990).