Enantioselective synthesis of the carbacephem antibiotic loracarbef via Mitsunobu and Dieckmann cyclization from an unnatural amino acid

Tetrahedron Letters

Volumn 44, Issue 32, 2003, Pages 5991-5993

  Misner, Jerry W ^a   Fisher, Jack W ^a   Gardner, John P ^a   Pedersen, Steve W ^a   Trinkle, Kristina L ^a   Jackson, Billy G ^a   Zhang, Tony Y ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALDEHYDE DERIVATIVE; AMINO ACID; BETA LACTAM ANTIBIOTIC; CARBACEPHEM DERIVATIVE; GLYCINE; LORACARBEF;

ALDOL REACTION; ARTICLE; CATALYSIS; CHROMATOGRAPHY; CYCLIZATION; DEPROTECTION REACTION; DIECKMANN REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; MITSUNOBU REACTION; POLYMERIZATION;

EID: 0037968009     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01483-7     Document Type: Article

References (10)

1. For examples of selective syntheses of 2, see: (a) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1985, 26, 3787; (b) 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.; Gardner, J. P.; Graves, B. J.; Hines, P.; Hoying, R. C.; Jackson, B. G.; Kinnick, M. D.; Kochert, C. D.; Lewis, J. S.; Luke, W. D.; Moore, L. L.; Morin, J. M., Jr.; Nist, R. L.; Prather, D. E.; Sparks, D. L.; Vladuchick, W. C. Tetrahedron Lett. 1989, 30, 232.
2. For examples of selective syntheses of 2, see: (a) Evans, D. A.; Sjogren, E. B. Tetrahedron Lett. 1985, 26, 3787; (b) 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.; Gardner, J. P.; Graves, B. J.; Hines, P.; Hoying, R. C.; Jackson, B. G.; Kinnick, M. D.; Kochert, C. D.; Lewis, J. S.; Luke, W. D.; Moore, L. L.; Morin, J. M., Jr.; Nist, R. L.; Prather, D. E.; Sparks, D. L.; Vladuchick, W. C. Tetrahedron Lett. 1989, 30, 232.
3. Dotzlaf, J. E.; Gazak, R. J.; Kreuzman, A. J.; Kroeff, E. P.; Queener, S. W.; Vicenzi, J. T.; Yeh, W. K.; Joseph Martin; Zock, J. M. Eur. Pat. 628638, 1995.
4. Jackson B.G., Pedersen S.W., Fisher J.W., Misner J.W., Gardner J.P., Staszak M.A., Doecke C., Rizzo J., Aikins J., Farkas E., Trinkle K.L., Vicenzi J., Reinhard M., Kroeff E.P., Higginbotham C.A., Gazak R.J., Zhang T.Y. Tetrahedron. 56:2000;5667.
5. For a review on Mitsunobu reaction, see: Hughes D.L. Org. React. 42:1992;336.
6. For the synthesis of β-lactams via Mitsunobu reaction, see: (a) Bose, A. K.; Manhas, M. S.; Sahu, D. P.; Hedge, V. R. Can. J. Chem. 1984, 62, 2498; (b) Bose, A. K.; Sahu, D. P.; Manhas, M. S. J. Org. Chem. 1981, 46, 1229; (c) Miller, M. J.; Morrison, M. A. J. Org. Chem. 1983, 48, 4421; (d) Galeotti, N.; Montagne, C.; Poncet, J.; Jouin, P. Tetrahedron Lett. 1992, 33, 2807.
7. For the synthesis of β-lactams via Mitsunobu reaction, see: (a) Bose, A. K.; Manhas, M. S.; Sahu, D. P.; Hedge, V. R. Can. J. Chem. 1984, 62, 2498; (b) Bose, A. K.; Sahu, D. P.; Manhas, M. S. J. Org. Chem. 1981, 46, 1229; (c) Miller, M. J.; Morrison, M. A. J. Org. Chem. 1983, 48, 4421; (d) Galeotti, N.; Montagne, C.; Poncet, J.; Jouin, P. Tetrahedron Lett. 1992, 33, 2807.
8. For the synthesis of β-lactams via Mitsunobu reaction, see: (a) Bose, A. K.; Manhas, M. S.; Sahu, D. P.; Hedge, V. R. Can. J. Chem. 1984, 62, 2498; (b) Bose, A. K.; Sahu, D. P.; Manhas, M. S. J. Org. Chem. 1981, 46, 1229; (c) Miller, M. J.; Morrison, M. A. J. Org. Chem. 1983, 48, 4421; (d) Galeotti, N.; Montagne, C.; Poncet, J.; Jouin, P. Tetrahedron Lett. 1992, 33, 2807.
9. For the synthesis of β-lactams via Mitsunobu reaction, see: (a) Bose, A. K.; Manhas, M. S.; Sahu, D. P.; Hedge, V. R. Can. J. Chem. 1984, 62, 2498; (b) Bose, A. K.; Sahu, D. P.; Manhas, M. S. J. Org. Chem. 1981, 46, 1229; (c) Miller, M. J.; Morrison, M. A. J. Org. Chem. 1983, 48, 4421; (d) Galeotti, N.; Montagne, C.; Poncet, J.; Jouin, P. Tetrahedron Lett. 1992, 33, 2807.
10. Jackson B.G., Gardner J.P., Heath P.C. Tetrahedron Lett. 31:1990;6317-6320.