Lipase-mediated synthesis of the enantiomeric forms of 4,5-epoxy4,5-dihydro-α-ionone, and 5,6-epoxy-5,6-dihydro-β-ionone. A new direct access to enantiopure (R)-, and (5)-α-ionone

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 3, 1999, Pages 271-278

  Aleu, Josefina ^a,b   Brcnna, Elisabctta ^a   Fuganti, Claudio ^a   Serra, Stefano ^a  

^a POLITECNICO DI MILANO   (Italy)

^b UNIVERSITY OF CÁDIZ   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33746490474     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808780f     Document Type: Article

References (26)

1. G. OhlofT, in Fortschritte tier Chemie lier organische Naturstoffe, ed. W. Herz, H. Griscbach, and G. W. Kirby, Springer, 1978, vol. 35, p.431.'
2. P. Karrer, and H. Stuerzinger, Heh. Chiin. Ada, 1946,29, 1829.
3. J. E. Ayers, M. J. Fishwick, D. G. Land, and T. Swain, Nature, 1964, 203,81.
4. F. Mueggler-Chavan, R. Viani, J. Bricout, J. P. Marion, H. Mechtler, D. Reymond, and R. H. Egli, fleh: Chim. Ada, 1969,52, 549.
5. G. Ohloffand S. Mignat, Annalen, 1962,652, 115.
6. A. Haae, W. Eschenmoser, and C. H. Eugster, Heh: Chim. Ada, 1980,63,10.
7. W. Eschenmoser, P. Uebelhart, and C. H. Eucster, Heh: Chim. Acta, 1981,64,2681.
8. M. Acemoglu, W. Eschenmoser, and C. H. Eugster, Heh: Chim. Acta, 1981,64, 2691.
9. A. Haag, and C. H. Eugster, lieh: Chim. Acta, 1982,65, 1975.
10. M. Acemoglu, and C. H. Eugster, fleh: Chim. Ada, 1984, 67, 184.
11. P. Uebelhart, A. Baumeier, H. Haag, R. Prewo, J. H. Bieri, and C. H. Eugster, Heh: Chim. Ada, 1986, 69,816.
12. H. Sobotka, E. Bloch, H. Chanmann, and E. Feldbau, J. Am. Chem. Soc., 1943,65,2061.
13. W. Eschenmoser, P. Ueberhalt, and C. H. Euaster, Heh: Chim. Ada, 1979,62,2534.
14. F. Toda, K. Mori, Y. Matsuura, and H. Akai, J. Clieni. Soc., Client. Commun., 1990, 1591.
15. C. Fehr, and O. Guntern, Heh: Chim. Ada, 1992,75, 1023!
16. E. Brenna, C. FÜganti, P. Grasselli, M. Redaelli, and S. Serra, J. Chem. Soc., Perkin Trans, l, 1998,4129.
17. R. Caputo, L. Mangoni, O. Neri, and G. Palumbo, Tetrahedron Lett., 1981,22,3551.
18. Throughout the \vhole work, as. for epoxy-a-ionol derivatives, diastereoisomeric excesses are used to express the ratio between the diastereoisomeric cis, and /rans-epoxides.
19. Enantiomeric ratio (E), and conversion (c) were calculated according to C. S. Chcn, Y. Fujimoto, G. Girdaukas, and C. J. Sih, J. Am. Chcm. Sac., 1982,104, 7294.
20. L. Lopez, G. Mêle, V. Paradiso, A. Nacci, and P. Mastrorilli, Ga::. Chim. //J., 1996,126, 725.
21. T. Oritani, and K. Yamashita, Phytochemistry, 1983,22, 1909.
22. J. A. Bajgrowicz, P. Kraft, and G. Frater, Tetrahedron, 1998,54,7633.
23. (a) C. Fehr, and O. Guntern, Heir. Chim..Acta, 1992, 75, 1023;
24. (ft) P. WerkholT, W. Bretschneider, M. Guentert, R. Hopp, and H. Surburg, Flavor Science, and Technology, ed. Y. Bessiere, and A. F. Thomas, Wiley, 1990, p. 33.
25. US Pat. 5416 069 priority CH, July 23, 1993 to Givaudan Roure; US Pat. 5 268 355 priority CH, March 3, 1992 to Firmenich.
26. S. Pereira, and M. Srebnik, Aldrichun. Acta, 1993,26, 17.