Chemoenzymatic resolution of cis- and trans-3,6-dihydroxy-α-ionone. Synthesis of the enantiomeric forms of dehydrovomifoliol and 8,9-dehydrotheaspirone

Tetrahedron Asymmetry

Volumn 18, Issue 21, 2007, Pages 2573-2580

  Serra, Stefano ^a   Barakat, Assem ^a   Fuganti, Claudio ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

3,6 DIHYDROXY ALPHA IONONE; 8,9 DEHYDROTHEASPIRONE; CAROTENOID; DEHYDROVOMIFOLIOL; IONONE DERIVATIVE; TERPENOID DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTALLIZATION; ENANTIOMER; HYDROGENATION; ISOMER; PRIORITY JOURNAL; SYNTHESIS;

EID: 36148932905     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.10.014     Document Type: Article

References (35)

1. Mayer H. Pure Appl. Chem. 51 (1979) 535-564
2. Pfander H. Pure Appl. Chem. 63 (1991) 23-33
3. Brenna E., Fuganti C., Serra S., and Kraft P. Eur. J. Org. Chem. (2002) 967-978
4. Serra S., Fuganti C., and Brenna E. Helv. Chim. Acta 89 (2006) 1110-1122
5. Brenna E., Fuganti C., and Serra S. C.R. Chim. 6 (2003) 529-546
6. Serra S., and Fuganti C. Tetrahedron: Asymmetry 17 (2006) 1573-1580
7. Brenna E., Fuganti C., and Serra S. Tetrahedron: Asymmetry 16 (2005) 1699-1704
8. Diallo B., and Vanhaelen M. Phytochemistry 26 (1987) 1491-1492
9. Achenbach H., Blümm E., and Waibel R. Tetrahedron Lett. 30 (1989) 3059-3060
10. Tsushima M., Mune E., Maoka T., and Matsuno T. J. Nat. Prod. 63 (2000) 960-964
11. Matsuno T., Tsushima M., and Maoka T. J. Nat. Prod. 64 (2001) 507-510
12. DellaGreca M., Di Marino C., Zarrelli A., and D'Abrosca B. J. Nat. Prod. 67 (2004) 1492-1495
13. Addicott F.T. Abscisic Acid (1983), Praeger, New York
14. Takasugi M., Anetai M., Katsui N., and Masamune T. Chem. Lett. (1973) 245-248
15. Achenbach H., Lottes M., Waibel R., Karikas G.A., Correa M.D., and Gupta M.P. Phytochemistry 38 (1995) 1537-1545
16. D'Arcy B.R., Rintoul G.B., Rowland C.Y., and Blackman A.J. J. Agric. Food Chem. 45 (1997) 1834-1843
17. Kai H., Baba M., and Okuyama T. Chem. Pharm. Bull. 55 (2007) 133-136
18. Roberts D.L., Heckman R.A., Hege B.P., and Bellin S.A. J. Org. Chem. 33 (1968) 3566-3569
19. Ohloff G. Scent and Fragrances: The Fascination of Fragrances and their Chemical Perspectives (1994), Springer, Berlin
20. Fujimori T., Takagi Y., and Kato K. Agric. Biol. Chem. 45 (1981) 2925-2926
21. Winterhalter P., Sefton M.A., and Williams P.J. J. Agric. Food Chem. 38 (1990) 1041-1048
22. Knapp H., Weigand C., Gloser J., and Winterhalter P. J. Agric. Food Chem. 45 (1997) 1309-1313
23. Surburg H., Güntert M., and Harder H. In: Teranishi R., Buttery R.G., and Sugisawa H. (Eds). Bioactive Volatile Compounds from Plants. ACS Symposium Series 525 (1993), American Chemical Society, Washington, DC 168-186
24. Koreeda M., Weiss G., and Nakanishi K. J. Am. Chem. Soc. 95 (1973) 239-240
25. Kim B.T., Min Y.K., Asami T., Park N.K., Kwon O.Y., Cho K.Y., and Yoshida S. Tetrahedron Lett. 38 (1997) 1797-1800
26. Hitomi, K.; Hideki, N.; Taro, K.; Masakazu, I. Japanese Patent, 2002, JP 2002069479 A.
27. Acemoglu M., Uebelhart P., Rey M., and Eugster C.H. Helv. Chim. Acta 71 (1988) 931-956
28. Meyers A.I., and Sturgess M.A. Tetrahedron Lett. 30 (1989) 1741-1744
29. Smith T.R., Clark A.J., Clarkson G.J., Taylor P.C., and Marsh A. Org. Biomol. Chem. 4 (2006) 4186-4192
30. Mori K. Tetrahedron 30 (1974) 1065-1072
31. Brenna E., Fuganti C., and Serra S. Tetrahedron: Asymmetry 14 (2003) 1-42
32. Abate A., Brenna E., Fuganti C., Gatti F.G., and Serra S. J. Mol. Catal. B: Enzym. 32 (2004) 33-51
33. Kato T., Kondo H., Kitano Y., Hata G., and Takagi Y. Chem. Lett. (1980) 757-760
34. Kato T., and Kondo H. Bull. Chem. Soc. Jpn. 54 (1981) 1573-1574
35. Strauss C.R., Dimitriadis E., Wilson B., and Williams P.J. J. Agric. Food Chem. 34 (1986) 145-149