Chemoenzymatic synthesis of unnatural amino acids via modified Claisen rearrangement of glycine enolates. Approach to morphine synthesis

Journal of Organic Chemistry

Volumn 62, Issue 5, 1997, Pages 1194-1195

  Gonzalez, David ^a   Schapiro, Valeria ^b   Seoane, Gustavo ^b   Hudlicky, Tomas ^a   Abboud, Khalil ^a  

^a University of Florida ^*  (United States)

^b UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; GLYCINE ENOLATE; MORPHINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NONHUMAN;

EID: 0030889520     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962315w     Document Type: Article

References (33)

1. Santaniello, E.; Ferraboschi, P.; Manzocchi, A. Chem. Rev. 1992, 92, 1071.
2. (a) Reed, J. W.; Hudlicky, T. in Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press, Inc.: Greenwich, CT, 1995; Vol. 1, p 271.
3. (b) Hudlicky, T. Chem. Rev. 1996, 96, 3.
4. (c) Hudlicky, T.; Thorpe, A. J. J. Chem. Soc., Chem. Commun. 1996, 1993.
5. (a) Hudlicky, T.; Seoane, G.; Price, J. D.; Gadamassetti, K. D. Synlett 1990, 433.
6. (b) Hudlicky, T.; Luna, H.; Olivo, H.; Andersen, C.; Nugent, T.; Price, J. D. J. Chem. Soc., Perkin Trans. 1 1991, 2907.
7. (c) Hudlicky, T.; Olivo, H. Tetrahedron Lett. 1991, 32, 6077.
8. (d) Hudlicky, T.; Natchus, M. J. Org. Chem. 1992, 57, 4740.
9. (e) Hudlicky, T.; Rouden, J.; Luna, H.; Allen, S. J. Am. Chem. Soc. 1994, 116, 5099.
10. (f) Hudlicky, T.; Olivo, H.; McKibben, B. J. Am. Chem. Soc. 1994, 116, 5118.
11. (g) Hudlicky, T.; Tian, X.; Königsberger, K. J. Am. Chem. Soc. 1995, 117, 3643.
12. (a) Hudlicky, T.; Boros C. H.; Boros, E. B. Synthesis 1992, 174.
13. (b) Butora, G.; Hudlicky, T.; Fearnley, S. P.; Gum, A. G.; Stabile, M. R.; Abboud, K. Tetrahedron Lett. 1996, 37, 8155.
14. (c) Butora, G.; Gum, A. G.; Hudlicky, T.; Abboud, K. Synthesis, submitted.
15. Butora, G.; Hudlicky, T.; Fearnley, S. P.; Gum, A. G.; Stabile, M. R. In Studies in Natural Products Chemistry; Rahman, A., Ed.; VCH: Weinheim, 1995; pp 43-154.
16. For recent reviews see ref 2 and: (a) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795. (b) Brown, S. M.; Hulicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, p 113. (c) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Enviroment; Anastas, P. T., Williamson, T., Eds.; Washington, DC, ACS Symposium Series No. 626; 1996; p 180.
17. For recent reviews see ref 2 and: (a) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795. (b) Brown, S. M.; Hulicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, p 113. (c) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Enviroment; Anastas, P. T., Williamson, T., Eds.; Washington, DC, ACS Symposium Series No. 626; 1996; p 180.
18. For recent reviews see ref 2 and: (a) Carless, H. A. J. Tetrahedron: Asymmetry 1992, 3, 795. (b) Brown, S. M.; Hulicky, T. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, p 113. (c) Hudlicky, T. In Green Chemistry: Designing Chemistry for the Enviroment; Anastas, P. T., Williamson, T., Eds.; Washington, DC, ACS Symposium Series No. 626; 1996; p 180.
19. Hudlicky, T.; Luna, H.; Barbieri, G.; Kwart, L. A. J. Am. Chem. Soc. 1988, 110, 4735
20. Engel, N.; Küber, B.; Steglich, W.; Angew. Chem., Int. Ed. Engl. 1977, 16, 394.
21. Bartlett, P. A.; Barstow, J. F. J. Org. Chem. 1982, 47, 3933.
22. (a) Cooper, J.; Knight, D. W.; Gallagher, P. T. J. Chem. Soc., Chem. Commun. 1987, 1220.
23. (b) Baumann, H.; Duthaler, R. O. Helv. Chim. Acta 1988, 71, 1025.
24. (a) Kazraaier, U. Angew. Chem., Int. Ed. Engl. 1994, 33, 1998
25. (b) Kazmaier, U. Tetrahedron 1994, 50, 12895.
26. (c) Kazmaier, U.; Maier, S. Tetrahedron 1996, 52, 941.
27. (d) Kazmaier, U.; Schneider, C. Synlett 1996, 975.
28. (a) Wipf, P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; Vol. 5, p 827.
29. (b) Ireland, R. E.; Maienfisch, P. J. Org. Chem. 1988, 53, 640.
30. Ireland, R. E.; Wipf, P.; Xiang, J. J. Org. Chem. 1991, 56, 3572.
31. Colombo, L.; Casiraghi, G.; Pittalis, A.; Rassu, G. J. Org. Chem. 1991, 56, 3897.
32. Gonzalez, D.; Schapiro, V.; Seoane, G.; Hudlicky, T. Tetrahedron: Asymmetry submitted.
33. The author has deposited atomic coordinates for 8a with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.