A solid-phase combinatorial method for the synthesis of novel 5- and 6-membered ring lactams

Tetrahedron Letters

Volumn 38, Issue 3, 1997, Pages 359-362

  Short, Kevin M ^a   Mjalli, Adnan Mm ^a  

^a Ontogen Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; LACTAM;

ARTICLE; DRUG SYNTHESIS; IMMOBILIZATION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0031022868     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02303-9     Document Type: Article

References (18)

1. (a); Gallop, M.A.; Barrett, R.W.; Dower, W.J.; Fodor, S.P.A.; Gordon, E.M. J. Med. Chem. 1994, 37, 1233.
2. (b); Gordon, E.M.; Barrett, R.W.; Dower, W.J.; Fodor, S.P.A.; Gallop, M.A. J. Med. Chem. 1994, 37, 1385.
3. (c); Thompson, L.A.; Ellman, J.A. Chem. Rev. 1996, 96, 555.
4. (a); Ugi, I.; Dömling, A.; Hörl, W. Endeavour 1994, 18, 115.
5. (b); Keating, T.A.; Armstrong, R.W. J. Am. Chem. Soc. 1995, 117, 7842.
6. (c); Cao, X.; Moran, E.J.; Siev, D.; Lio, A.; Ohashi, C.; Mjalli, A.M.M. Bio. Med. Chem. Lett. 1995, 5, 2953.
7. (d); Ugi, I., Achatz, J.; Baumgartner-Rupnik, M.; Danzer, B.; Fleck, C.; Glahsl, G.; Herrmann, R.; Jacob, P.; Kambach, C. et.al. Nat. Prod. Chem. 3 1988, 107.
8. (a); Sarshar, S.; Siev, D.; Mjalli, A.M.M. Tet. Lett. 1996, 37, 835.
9. (b); Zhang, C.; Moran, E.J.; Woiwode, T.F.; Short, K.M.; Mjalli, A.M.M. Tet. Lett. 1996, 37, 751.
10. Mjalli, A.M.M.; Sarshar, S.; Baiga, T.J. Tet. Lett. 1996, 37, 2943.
11. For recent reviews on β-lactam antibiotics, see: Neuhaus, F.C.; Georgopapadakou, N.H., in Emerging Targets in Antibacterial and Antifungal Chemotherapy, Stutcliffe, J.; Georgopapadakou, N.H., Ed. Chapman and Hall, New York, 1992.
12. Dugar, S.; Kirkup, M.P.; Clader, J.W.; Lin, S-I.; Rizvi, R.; Snow, M.E.; Davis, H.R. Jr.; McCombie, S.W. Bio. Med. Chem. Lett. 1995, 5, 2947.
13. Napoletano, M.; Della Bella, D.; Fraire, C.; Grancini, G.; Masotto, C.; Ricciardi, S.; Zambon, C. Bio. Med. Chem. Lett. 1995, 5, 589.
14. Istitulo DeAngeli S.p.A., European Patent EP 404737, 1990.
15. β-Lactams have been prepared from β-alanine and derivatives thereof: Isenring, H.R.; Hofheinz, W. Synthesis, 1981, 385. Eckert, H.; Ugi, I. Studies in Natural Product Chemistry 1993, 12, 113.
16. β-Lactams have been prepared from β-alanine and derivatives thereof: Isenring, H.R.; Hofheinz, W. Synthesis, 1981, 385. Eckert, H.; Ugi, I. Studies in Natural Product Chemistry 1993, 12, 113.
17. Indeed, Ugi discussed the possibility (ref. 2(d)) that lactams would be formed from ω-carboxyaldehydes. A search of the ACD (Available Chemicals Directory, MDL information systems) showed that only one γ-or δ-carboxyaldehyde is commercially available (succinic semialdehyde).
18. Prepared in an analogous manner in three steps from 6-aminohexanoic acid (see ref. 3(b)).