Enantioselective syntheses of 1-carbacephalosporins from chemoenzymically derived β-hydroxy-α-amino acids: Applications to the total synthesis of carbacephem antibiotic loracarbef

Tetrahedron

Volumn 56, Issue 31, 2000, Pages 5667-5677

  Jackson, Billy G ^a   Pedersen, Steve W ^a   Fisher, Jack W ^a   Misner, Jerry W ^a   Gardner, John P ^a   Staszak, Michael A ^a   Doecke, Christopher ^a   Rizzo, John ^a   Aikins, James ^a   Farkas, Eugene ^a   Trinkle, Kristina L ^a   Vicenzi, Jeffrey ^a   Reinhard, Matt ^a   Kroeff, Eugene P ^a   Higginbotham, Chris A ^a   Gazak, R J ^a   Zhang, Tony Y ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

Aldolase; Antibacterials; Biocatalysis; Carbacephalos porins; Cephalosporins; Loracarbef; Serine hydroxymethyltransferase; SHMT; Hydroxy amino acid; Lactam

Indexed keywords

AMINO ACID DERIVATIVE; CARBACEPHEM DERIVATIVE; CEPHALOSPORIN DERIVATIVE; LORACARBEF;

CHEMICAL REACTION; CHEMICAL STRUCTURE; CONFERENCE PAPER; CYCLIZATION; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0034725793     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00416-6     Document Type: Conference Paper

References (57)

1. Garcia-Rodriguez J.A., Bellido J.L.M., Sanchez J.E.G. Int. J. Antimicrob. Agents. 5:1995;231-243.
2. Garau J. Diagn. Microbiol. Infect. Dis. 31:1998;479-480.
3. Georg G.I. The Organic Chemistry of β-Lactams. 1993.
4. Kaufman A.H., Baum J. Textb. Ocul. Pharmacol. 1997;473-491.
5. Marshall W.F., Blair J.E. Mayo Clin. Proc. 74:1999;187-195.
6. Moellering, J. R. C., Ed. Oral Cephalosporins [In: Antibiot. Chemother. (Basel), 1995; 47], 1995.
7. Wise, R. Antibiot. Chemother. (7th Ed.) 1997, 202-255.
8. Zhang T.Y., Hatfield L.D. Compr. Heterocycl. Chem. II. 1B:1996;591-622.
9. Force R.W., Nahata M.C. Ann. Pharmacother. 27:1993;321-410.
10. Zeckel M.L., Therasse D.G. Drugs Today. 31:1995;351-355.
11. Fassbender M., Lode H., Schaberg T., Borner K., Koeppe P. Clin. Infect. Dis. 16:1993;646-653.
12. Yamashita K., Shimizu M., Motizuki H., Sato K. Chemotherapy (Tokyo). 41:1993;63-69.
13. Brogden R.N., McTavish D. Drugs. 45:1993;716-736.
14. Matsukuma I., Yoshiye S., Mochida K., Hashimoto Y., Sato K., Okachi R., Hirata T. Chem. Pharm. Bull. 37:1989;1239-1244.
15. Beeter J.B., Hall D.A., Jordan C.L., Justice R.M., Kinnick M.D., Morin J.M. Jr, Paschal J.W., Ternansky R.J. Tetrahedron Lett. 34:1993;3051-3054.
16. Bodurow C.C., Boyer B.D., Brennan J., Bunnell C.A., Burks J.E., Carr M.A., Doecke C.W., Eckrich T.M., Fisher J.W., et al. Tetrahedron Lett. 30:1989;2321-2324.
17. Evans D.A., Sjogren E.B. Tetrahedron Lett. 26:1985;3783-3786.
18. Evans D.A., Sjogren E.B. Tetrahedron Lett. 26:1985;3787-3790.
19. Briggs B.S., Wright I.G., Zmijewski M.J., Levy J.N., Stukus M. New J. Chem. 18:1994;425-434.
20. Zmijewski M.J. Jr, Briggs B.S., Thompson A.R., Wright I.G. Tetrahedron Lett. 32:1991;1621-1622.
21. Miller M.J., Mattingly P.G. Tetrahedron. 39:1983;2563.
22. Bodurow C.C., Levy J.N., Wiitala K.W. Tetrahedron Lett. 33:1992;4283-4286.
23. Aikins, J. A.; Blaszczak, L. C.; Lund, K. P.; Rizzo, J. R. EP 672656 CA:AN 1995: 987974.
24. Blaszczak L.C., Armour H.K., Halligan N.G. Tetrahedron Lett. 31:1990;5693-5696.
25. Dunigan J., Weigel L.O. J. Org. Chem. 56:1991;6225-6227.
26. Frazier J.W., Staszak M.A., Weigel L.O. Tetrahedron Lett. 33:1992;857-860.
27. Ma C., Miller M.J. Tetrahedron Lett. 32:1991;2577-2580.
28. Teng M., Miller M.J. J. Am. Chem. Soc. 115:1993;548-554.
29. Teng M., Gasparski C.M., Williams M.A., Miller M.J. Bioorg. Med. Chem. Lett. 3:1993;2431-2436.
30. Teng M., Miller M.J., Nicas T.I., Grissom-Arnold J., Cooper R.D.G. Bioorg. Med. Chem. 1:1993;151-154.
31. Floyd D.M., Fritz A.W., Pluscec J., Weaver E.R., Cimarusti C.M. J. Org. Chem. 47:1982;5160-5167.
32. Cimarusti C.M., Bonner D.P., Breuer H., Chang H.W., Fritz A.W., Floyd D.M., Kissick T.P., Koster W.H., Kronenthal D., et al. Tetrahedron. 39:1983;2577-2589.
33. Miller M.J. Tetrahedron. 52:1996;4225-4238.
34. Guzzo P.R., Miller M.J. J. Org. Chem. 59:1994;4862-4867.
35. Oliver D.J., Raman R. J. Bioenerg. Biomembr. 27:1995;407-414.
36. Rao N.A. New Trends Biol. Chem. 1991;333-340.
37. Kisliuk R.L. Chemtracts: Biochem. Mol. Biol. 2:1991;217-220.
38. Matthews R.G., Drummond J.T. Chem. Rev. 90:1990;1275-1290.
39. Brody T. Pteridines. 1:1989;159-165.
40. Rao N.A., Ramesh K.S., Ratnam M., Rao D.N., Vijayalakshmi D., Bhaskaran N. J. Sci. Ind. Res. 46:1987;248-260.
41. Schirch L. Folates Pterins. 1:1984;399-431.
42. Lotz B.T., Gasparski C.M., Peterson K., Miller M.J. J. Chem. Soc., Chem. Commun. 1990;1107-1109.
43. Miller, M. J. EP 460883 CA:116:233923.
44. Martini F., Angelaccio S., Pascarella S., Barra D., Bossa F., Schirch V. J. Biol. Chem. 262:1987;5499-5509.
45. Bossa F., Barra D., Martini F., Schirch L.V., Fasella P. Eur. J. Biochem. 70:1976;397-401.
46. Martini F., Maras B., Tanci P., Angelaccio S., Pascarella S., Barra D., Bossa F., Schirch V. J. Biol. Chem. 264:1989;8509-8519.
47. Kreuzman A.J., Zock J.M., Dotzlaf J.E., Vicenzi J.T., Queener S.W., Yeh W.K. J. Ind. Microbiol. Biotechnol. 19:1997;369-377.
48. Aswad D.W. Anal. Biochem. 137:1984;405-409.
49. Hoffman C., Tanke R.S., Miller M.J. J. Org. Chem. 54:1989;3750-3751.
50. Jackson B.G., Gardner J.P., Heath P.C. Tetrahedron Lett. 31:1990;6317-6320.
51. Miller, M. J.; Biswas, A.; Krook, M. A.; Woulfe, S. R. Proceedings from the Third International Symposium on Recent Advances in the Chemistry of β-Lactam Antibiotics; 1984; pp 305-317.
52. Bose A.K., Manhas M.S., Sahu D.P., Hegde V.R. Can. J. Chem. 62:1984;2498-2505.
53. Doecke C.W., Staszak M.A., Luke W.D. Synthesis. 1991;985.
54. Schirch L. Meister A. Advances in Enzymyology. 1982;83-112 Wiley, New York.
55. Haines A. Methods for the Oxidation of Organic Compounds Alkanes, Alkenes, Alkynes, and Arenes. 1985;Academic Press, London. pp 119-122, 146-148, 325-326.
56. Razumouski S.D., Zaikov G.E. Ozone and Its Reactions with Organic Compounds. 1984;Elsevier, Amsterdam.
57. Dancanale E., Montanari F. J. Org. Chem. 51:1986;567.