Synthesis and biological resolution of condensed bicyclic isoparaconic acid derivatives

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 16, 2000, Pages 2839-2842

  Drioli, Sara ^a   Felluga, Fulvia ^a   Forzato, Cristina ^a   Pitacco, Giuliana ^a   Valentin, Ennio ^a  

^a UNIVERSITY OF TRIESTE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; DEGRADATION; DERIVATIVES; ENZYMES; ESTERS; ISOMERS; REDUCTION;

BIOTRANSFORMATIONS;

ACETIC ACID;

EID: 0034699187     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b001615m     Document Type: Article

References (31)

1. (a) N. H. Fischer, E. J. Olivier and H. D. Fischer, Fortschr. Chem. Org. Naturst., 1979, 38, 47;
2. (b) T. K. Devon and A. I. Scott, in Handbook of Naturally, Occurring Compounds, Academic Press, New York, 1975, vol. 1;
3. (c) H. C. Brown, S. K. Kulkarni and U. S. Racherla, J. Org. Chem., 1994, 59, 365 and references cited therein.
4. R. B. Silverman, Farmaro, 1997, 52, 343.
5. (a) P. A. Grieco, Synthesis, 1975, 67;
6. (b) H. M.-R. Hoffmann and J. Rabe, Angew. Chem., Int. Ed. Engl., 1985, 24, 94;
7. (c) N. Petragnani, H. M. C. Ferraz and G. V. J. Silva, Synthesis,: 1986, 157;
8. (d) Y.-L. Chen, T.-C. Wans, C.-C. Tzeng and N.-C. Chang, Helv. Chim. Acta, 1999, 82, 191.
9. (a) F. Felluga, P. Nitti, G. Pitacco and E. Valentin, Gazz. Chim. Ital., 1993, 123, 443;
10. (b) C. Forzato, P. Nitti, G. Pitacco and E. Valentin, Gazz. Chim. Ital., 1995, 125, 223;
11. (c) C. Forzato, P. Nitti, G. Pitacco and E. Valentin, Gazz. Chim. Ital., 1996, 126, 37.
12. (a) S. Drioli, F. Felluga, C. Forzato, P. Nitti and G. Pitacco, Chem. Commun., 1996, 1289;
13. (b) S. Drioli, F. Felluga, C. Forzato, P. Nitti, G. Pitacco and E. Valentin, J. Mol Catal. B: Enzym., 1997, 3, 203;
14. (c) S. Drioli, F. Felluga, C. Forzato, P. Nitti, G. Pitacco and E. Valentin, J. Org. Chem., 1998, 63, 2385.
15. Rodd's Chemistry of Carbon Compounds, ed. S. Coffey, Elsevier, Amsterdam, 1965, vol. 1, part D, p. 352.
16. K. C. Brannock, R. D. Burpitt, V. W. Goodlett and J. G. Thweatt, J. Org. Chem., 1964, 29, 813.
17. M. Calligaris, G. Pitacco, E. Valentin and E. Zotti, J. Org. Chem., 1977, 42, 2721.
18. Enamines: Synthesis, Structure and Reactions, ed. A. G. Cook., Marcel Dekker, New York, 1988, ch. 4.
19. L. M. Jackman and S. Sternhell, Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry, Pergamon Press, Oxford, 1969, p. 291.
20. C.-S. Chen, Y. Fuyimoto, G. Girdaukas and C. Sih, J. Am. Chem. Soc., 1982, 104, 7294.
21. (a) J. A. Marshall and N. Cohen, J. Org. Chem., 1965, 30, 3475;
22. (b) P. A. Grieco and M. Miyashita, J. Org. Chem. 1974, 39, 120;
23. (c) N. Petragnani and H. M. C. Ferraz, Synthesis, 1978, 476;
24. (d) G. Haaima, L. R. Hanton, M.-J. Lynch, S. D. Mawson, A. Routledge and R: T. Weavers, Tetrahedron, 1994, 50, 2161;
25. (e) G. T. Crisp and A. G. Meyer, Tetrahedron, 1995, 51, 5831;
26. (f) V. J. Bryan and T.-H. Chan, Tetrahedron Lett., 1996, 37, 5341.
27. J. K. Kochi, J. Am. Chem. Soc., 1965, 87, 1811.
28. M. Ganaha, Y. Funabiki, M. Motoki, S. Yamauchi and Y. Kinoshita, Biosci. Biotechnol. Biochem. 1998, 62 (1), 181.
29. C. C. Silveira, M. A. Araujo, E. J. Lenardao, A. L. Braga and M. J. Dabdoub, Synthesis 1995, 1305.
30. T. Okuda, S. Harigayo and A. Kiyomoto, Chem. Pharm. Bull Jpn., 1964, 12, 504.
31. C. Forzato, P. Nitti and G. Pitacco, Tetrahedron: Asymmetry, 1997, 8, 4101.