Bryophyte constituents; 7: New synthesis of (+)-rosmarinic acid and related compounds

Synthesis

Volumn , Issue 6, 1996, Pages 755-762

  Eicher, Theophil ^a   Ott, Markus ^a   Speicher, Andreas ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

allyl protective group; bryophyte constituents; chemoenzymatic resolution; rosmarinic acid; total synthesis

Indexed keywords

ROSMARINIC ACID;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOMER; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029793220     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4289     Document Type: Article

References (44)

1. (a) Scarpati, M.L.; Oriente, G. Ricerca Scientifica 1958, 28, 2329; Chem. Abstr. 1959, 53, 19955.
2. (a) Scarpati, M.L.; Oriente, G. Ricerca Scientifica 1958, 28, 2329; Chem. Abstr. 1959, 53, 19955.
3. (a) Hiller, K. Pharmazie 1965, 20, 574.
4. (b) Ellis, G.N.; Towers, G.H.N. Biochem. J. 1970, 118, 291.
5. Yazaki, K.; Fukui, H.; Tabata, M. Phytochemistry 1986, 1629; ibid. 1984, 2398.
6. Yazaki, K.; Fukui, H.; Tabata, M. Phytochemistry 1986, 1629; ibid. 1984, 2398.
7. Tamura, H.; Fujiwara, M.; Sugisawa, H. Agric. Biol. Chem. 1989, 1971.
8. Takeda, R.; Hasegawa, J.; Shinozaki, M. Tetrahedron Lett. 1990, 31, 4159.
9. Trennheuser, F.; Becker, H. Fachbereich 12, Universität des Saarlandes, D-66041 Saarbrücken, unpublished results. Trennheuser, F. Ph. D. Dissertation, 1992. University of Saarbrücken, 1992.
10. Zenk, M.; Etschenberg, E.; Graf, E. U. S. Patent 4329361, 1982 (A. Natterman & Cie. GmbH); Chem. Abstr. 1981, 95, 121158.
11. Pabsch, K.; Petersen, M.; Rao, N.N.; Alfermann, A.W.; Wandrey, C. Recl. Trav. Chim. Pays-Bas 1991, 110, 199.
12. Zinsmeister, H.D.; Becker, H.; Eicher, T. Angew. Chem. 1991, 103, 134; Angew. Chem. Int. Ed. Engl. 1991, 30, 130.
13. Zinsmeister, H.D.; Becker, H.; Eicher, T. Angew. Chem. 1991, 103, 134; Angew. Chem. Int. Ed. Engl. 1991, 30, 130.
14. (a) Buck, J.S.; Zimmermann, F.J. Org. Svnth. 1938, 18, 75.
15. (b) Harington, C.R.; Randall, J. J. Biochem. 1931, 25, 1028.
16. (c) Wong, H.; Xu, Z.; Chang, H.; Ju, C. Synthesis 1992, 793.
17. 3 or purified by bulb-to-bulb distillation, yield: 93%). See also: Sieber, P. Helv. Chim. Acta 1977, 60, 2710. Speier, J.L.; Webster, J.A.; Barnes, G.H. J. Am. Chem. Soc. 1957, 79, 974.
18. 3 or purified by bulb-to-bulb distillation, yield: 93%). See also: Sieber, P. Helv. Chim. Acta 1977, 60, 2710. Speier, J.L.; Webster, J.A.; Barnes, G.H. J. Am. Chem. Soc. 1957, 79, 974.
19. Schmidt, E.; Däbritz, E.; Thulke, K.; Grassmann, E. Liebigs Ann. Chem. 1965, 685, 161. The analogous N,N′-dicyclohexyl-O-allylisourea was prepared from the less expensive DCC (rapid bulb-to-bulb, distillation yield: 82%) and can be also used.
20. (a) Schöpf, C.; Brass, E. Liebigs Ann. Chem. 1940, 544, 30.
21. (b) Neish, A.C. Can. J. Biochem. Biophysiol. 1959, 37, 1431.
22. (a) Gerlach, H. Helv. Chim. Acta 1977, 60, 860.
23. (b) Sieber, P. ibid. 1977, 60, 2710.
24. (a) Kunz, H.; Waldmann, H.; Klinkhammer, U. Helv. Chim. Acta 1988, 71, 1868.
25. (b) Kunz, H.; Waldmann, H. Angew. Chem. 1985, 97, 885; Angew. Chem. Int. Ed. Engl. 1985, 24, 883.
26. (b) Kunz, H.; Waldmann, H. Angew. Chem. 1985, 97, 885; Angew. Chem. Int. Ed. Engl. 1985, 24, 883.
27. Kagan, H.B. J. Am. Chem. Soc. 1972, 94, 6429. Abel, E., Bennett, M.A.; Wilkinson, G. J. Chem. Soc. 1959, 3178.
28. Kagan, H.B. J. Am. Chem. Soc. 1972, 94, 6429. Abel, E., Bennett, M.A.; Wilkinson, G. J. Chem. Soc. 1959, 3178.
29. (a) Noyori, R. J. Am. Chem. Soc. 1987, 109, 5856; ibid. 1988, 110, 629.
30. (a) Noyori, R. J. Am. Chem. Soc. 1987, 109, 5856; ibid. 1988, 110, 629.
31. (b) Noyori, R. Acc. Chem. Res. 1990, 23, 345.
32. (c) Noyori, R. Tetrahedron Lett. 1991, 32, 4163.
33. Basler, H.-U. Tetrahedron: Asymmetry 1991, 2, 843.
34. Brown, H.C.; Cho, B.T.; Park, W.S. J. Org. Chem. 1988, 53, 1231.
35. Kolb, H.C.; Hoffmann, M.R. Tetrahedron: Asymmetry 1990, 1, 237.
36. Drauz, K.; Waldmann, H. Eds.; Enzyme Catalysis in Organic Synthesis, VCH: Weinheim, 1995.
37. Only few examples are reported for the enzymatic resolution of aryl lactic acids and esters, e.g. Scilimati, A.; Ngooi, T.K.; Sih, C.J. Tetrahedron Lett. 1988, 28, 4927; Lefker, B.A.; Hada, W.A.; McGarry, P.J. Tetrahedron Lett. 1994, 35, 5205.
38. Only few examples are reported for the enzymatic resolution of aryl lactic acids and esters, e.g. Scilimati, A.; Ngooi, T.K.; Sih, C.J. Tetrahedron Lett. 1988, 28, 4927; Lefker, B.A.; Hada, W.A.; McGarry, P.J. Tetrahedron Lett. 1994, 35, 5205.
39. Bevinakatti, H.S.; Banerji, A.A.; Newadkar, R.V. J. Org. Chem. 1989, 54, 2453.
40. Wang, Y.; Lalonde, J.; Momongan, M.; Bergbreiter, D.E.; Wong, C. J. Am. Chem. Soc. 1988, 110, 7200.
41. Lefker, B.A.; Hada, W.A.; McGarry, P.J. Tetrahedron Lett. 1994, 35, 5205.
42. Oberhauser, Th.; Bodenteich, M.; Faber, K.; Penn, G.; Griengl, H. Tetrahedron 1987, 43, 3931.
43. Sugosawa, S.; Tsuda, T. Chem. Zentralblatt 1936, 2559.
44. Coulson, D.R. Inorg. Synth. 1972, 13, 121.