Solid-Phase Synthesis of β-Lactams via the Miller Hydroxamate Approach

Organic Letters

Volumn 3, Issue 3, 2001, Pages 337-340

  Meloni, Marco Massimiliano ^a   Taddei, Maurizio ^a  

^a UNIVERSITY OF SASSARI   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; BETA LACTAM; HYDROXAMIC ACID; HYDROXYLAMINE; POLYSTYRENE DERIVATIVE; SERINE; THREONINE;

ARTICLE; CHEMISTRY; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BETA-LACTAMS; HYDROXAMIC ACIDS; HYDROXYLAMINES; POLYSTYRENES; SERINE; THREONINE;

EID: 0035825754     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006779z     Document Type: Article

References (35)

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6. See; (a) Ruhland, B.; Bhandari, A.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1996, 118, 253. (b) Pei, Y.; Houghten, R. A.; Kiely, J. S. Tetrahedron Lett. 1997, 38, 3349. (c) Singh, R.; Nuss, J. M. Tetrahedron Lett. 1999, 40, 1249. (d) Molteni, V.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Benaglia, M. Tetrahedron Lett. 1998, 39, 1257. (e) Furman, B.; Thurmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121. (f) Delpiccolo, M. L.; Mata, E. G. Tetrahedron: Asymmetry 1999, 10, 3893. (g) Benaglia, M.; Cinquini, M.; Cozzi, F. Tetrahedron Lett. 1999, 40, 2019. (h) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F. Chem. Eur. J. 2000, 6, 133. (i) Schunk, S.; Enders, D. Org. Lett. 2000, 2, 907 (j) Hafez, A. M.; Taggi, A. E.; Wack, H.; Drury, W. J., III; Lectka, T. Org. Lett. 2000, 2, 3963.
7. See; (a) Ruhland, B.; Bhandari, A.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1996, 118, 253. (b) Pei, Y.; Houghten, R. A.; Kiely, J. S. Tetrahedron Lett. 1997, 38, 3349. (c) Singh, R.; Nuss, J. M. Tetrahedron Lett. 1999, 40, 1249. (d) Molteni, V.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Benaglia, M. Tetrahedron Lett. 1998, 39, 1257. (e) Furman, B.; Thurmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121. (f) Delpiccolo, M. L.; Mata, E. G. Tetrahedron: Asymmetry 1999, 10, 3893. (g) Benaglia, M.; Cinquini, M.; Cozzi, F. Tetrahedron Lett. 1999, 40, 2019. (h) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F. Chem. Eur. J. 2000, 6, 133. (i) Schunk, S.; Enders, D. Org. Lett. 2000, 2, 907 (j) Hafez, A. M.; Taggi, A. E.; Wack, H.; Drury, W. J., III; Lectka, T. Org. Lett. 2000, 2, 3963.
8. See; (a) Ruhland, B.; Bhandari, A.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1996, 118, 253. (b) Pei, Y.; Houghten, R. A.; Kiely, J. S. Tetrahedron Lett. 1997, 38, 3349. (c) Singh, R.; Nuss, J. M. Tetrahedron Lett. 1999, 40, 1249. (d) Molteni, V.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Benaglia, M. Tetrahedron Lett. 1998, 39, 1257. (e) Furman, B.; Thurmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121. (f) Delpiccolo, M. L.; Mata, E. G. Tetrahedron: Asymmetry 1999, 10, 3893. (g) Benaglia, M.; Cinquini, M.; Cozzi, F. Tetrahedron Lett. 1999, 40, 2019. (h) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F. Chem. Eur. J. 2000, 6, 133. (i) Schunk, S.; Enders, D. Org. Lett. 2000, 2, 907 (j) Hafez, A. M.; Taggi, A. E.; Wack, H.; Drury, W. J., III; Lectka, T. Org. Lett. 2000, 2, 3963.
9. See; (a) Ruhland, B.; Bhandari, A.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1996, 118, 253. (b) Pei, Y.; Houghten, R. A.; Kiely, J. S. Tetrahedron Lett. 1997, 38, 3349. (c) Singh, R.; Nuss, J. M. Tetrahedron Lett. 1999, 40, 1249. (d) Molteni, V.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Benaglia, M. Tetrahedron Lett. 1998, 39, 1257. (e) Furman, B.; Thurmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121. (f) Delpiccolo, M. L.; Mata, E. G. Tetrahedron: Asymmetry 1999, 10, 3893. (g) Benaglia, M.; Cinquini, M.; Cozzi, F. Tetrahedron Lett. 1999, 40, 2019. (h) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F. Chem. Eur. J. 2000, 6, 133. (i) Schunk, S.; Enders, D. Org. Lett. 2000, 2, 907 (j) Hafez, A. M.; Taggi, A. E.; Wack, H.; Drury, W. J., III; Lectka, T. Org. Lett. 2000, 2, 3963.
10. See; (a) Ruhland, B.; Bhandari, A.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1996, 118, 253. (b) Pei, Y.; Houghten, R. A.; Kiely, J. S. Tetrahedron Lett. 1997, 38, 3349. (c) Singh, R.; Nuss, J. M. Tetrahedron Lett. 1999, 40, 1249. (d) Molteni, V.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Benaglia, M. Tetrahedron Lett. 1998, 39, 1257. (e) Furman, B.; Thurmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121. (f) Delpiccolo, M. L.; Mata, E. G. Tetrahedron: Asymmetry 1999, 10, 3893. (g) Benaglia, M.; Cinquini, M.; Cozzi, F. Tetrahedron Lett. 1999, 40, 2019. (h) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F. Chem. Eur. J. 2000, 6, 133. (i) Schunk, S.; Enders, D. Org. Lett. 2000, 2, 907 (j) Hafez, A. M.; Taggi, A. E.; Wack, H.; Drury, W. J., III; Lectka, T. Org. Lett. 2000, 2, 3963.
11. See; (a) Ruhland, B.; Bhandari, A.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1996, 118, 253. (b) Pei, Y.; Houghten, R. A.; Kiely, J. S. Tetrahedron Lett. 1997, 38, 3349. (c) Singh, R.; Nuss, J. M. Tetrahedron Lett. 1999, 40, 1249. (d) Molteni, V.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Benaglia, M. Tetrahedron Lett. 1998, 39, 1257. (e) Furman, B.; Thurmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121. (f) Delpiccolo, M. L.; Mata, E. G. Tetrahedron: Asymmetry 1999, 10, 3893. (g) Benaglia, M.; Cinquini, M.; Cozzi, F. Tetrahedron Lett. 1999, 40, 2019. (h) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F. Chem. Eur. J. 2000, 6, 133. (i) Schunk, S.; Enders, D. Org. Lett. 2000, 2, 907 (j) Hafez, A. M.; Taggi, A. E.; Wack, H.; Drury, W. J., III; Lectka, T. Org. Lett. 2000, 2, 3963.
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14. See; (a) Ruhland, B.; Bhandari, A.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1996, 118, 253. (b) Pei, Y.; Houghten, R. A.; Kiely, J. S. Tetrahedron Lett. 1997, 38, 3349. (c) Singh, R.; Nuss, J. M. Tetrahedron Lett. 1999, 40, 1249. (d) Molteni, V.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Benaglia, M. Tetrahedron Lett. 1998, 39, 1257. (e) Furman, B.; Thurmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121. (f) Delpiccolo, M. L.; Mata, E. G. Tetrahedron: Asymmetry 1999, 10, 3893. (g) Benaglia, M.; Cinquini, M.; Cozzi, F. Tetrahedron Lett. 1999, 40, 2019. (h) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F. Chem. Eur. J. 2000, 6, 133. (i) Schunk, S.; Enders, D. Org. Lett. 2000, 2, 907 (j) Hafez, A. M.; Taggi, A. E.; Wack, H.; Drury, W. J., III; Lectka, T. Org. Lett. 2000, 2, 3963.
15. See; (a) Ruhland, B.; Bhandari, A.; Gordon, E. M.; Gallop, M. A. J. Am. Chem. Soc. 1996, 118, 253. (b) Pei, Y.; Houghten, R. A.; Kiely, J. S. Tetrahedron Lett. 1997, 38, 3349. (c) Singh, R.; Nuss, J. M. Tetrahedron Lett. 1999, 40, 1249. (d) Molteni, V.; Annunziata, R.; Cinquini, M.; Cozzi, F.; Benaglia, M. Tetrahedron Lett. 1998, 39, 1257. (e) Furman, B.; Thurmer, R.; Kaluza, Z.; Lysek, R.; Voelter, W.; Chmielewski, M. Angew. Chem., Int. Ed. 1999, 38, 1121. (f) Delpiccolo, M. L.; Mata, E. G. Tetrahedron: Asymmetry 1999, 10, 3893. (g) Benaglia, M.; Cinquini, M.; Cozzi, F. Tetrahedron Lett. 1999, 40, 2019. (h) Annunziata, R.; Benaglia, M.; Cinquini, M.; Cozzi, F. Chem. Eur. J. 2000, 6, 133. (i) Schunk, S.; Enders, D. Org. Lett. 2000, 2, 907 (j) Hafez, A. M.; Taggi, A. E.; Wack, H.; Drury, W. J., III; Lectka, T. Org. Lett. 2000, 2, 3963.
16. Filigheddu, S. N.; Taddei, M. Tetrahedron Lett. 1998, 39, 3853. Filigheddu, S. N.; Masala, S.; Taddei, M. Tetrahedron Lett. 1999, 40, 6503.
17. Filigheddu, S. N.; Taddei, M. Tetrahedron Lett. 1998, 39, 3853. Filigheddu, S. N.; Masala, S.; Taddei, M. Tetrahedron Lett. 1999, 40, 6503.
18. For a comprehensive review on the possible synthetic approaches to azetidinones see: Perrone, E.; Franceschi, G. In Recent Progress in the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin, 1990; p 613.
19. Miller, M. J.; Mattingly, P. G.; Morrison, M. A.; Kerwin, J. F., Jr. J. Am. Chem. Soc. 1980, 102, 7026.
20. Mellor, S. L.; McGuire, C.; Chan, W. C. Tetrahedron Lett. 1997, 38, 3311. Different linkers, such as, for example, a Wang-type resin carrying an hydroxylamine group, were also tried with unsatisfactory results.
21. (4,6-Dimethoxy-[1,3,5]-triazin-2-yl)-4-methyl-morpholinium chloride. See: Falchi, A.; Giacomelli, G.; Porcheddu, A.; Taddei, M. Synlett 2000, 277. DMTMM is commercially available from Acros Organics.
22. 2 of hydroxylamine does not give a fully positive ninhydrine test. Following Kaiser's conditions we osberved, for compound 3, a pale yellow solution and red beads (microscope, 10X). After the coupling, the test was completely negative (uncolored beads). For Kaiser's test see: Kaiser, E.; Colescott, R. L.: Bossinger, C. D.; Cook, P. I. Anal. Biochem. 1970, 34, 595
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24. Distillation should be conducted using a temperature-controlled bath because of the danger of explosion on overheating DEAD. See: Pansare, S. V.; Huyer, G.; Arnold, L. D.; Vederas, J. C. Org. Synth. 1991, 70, 1.
25. Myers, R. M.; Langston, S. P.; Conway, S. P.; Abell, C. Org. Lett. 2000, 2, 1349. See also: Yang, H. W.; Romo, D. J. Org. Chem. 1999, 64, 7657.
26. Myers, R. M.; Langston, S. P.; Conway, S. P.; Abell, C. Org. Lett. 2000, 2, 1349. See also: Yang, H. W.; Romo, D. J. Org. Chem. 1999, 64, 7657.
27. -1) 1760. See: Woulfe, S. R.; Miller, M. J. J. Org. Chem. 1986, 51, 3133
28. -1) 1760. See: Woulfe, S. R.; Miller, M. J. J. Org. Chem. 1986, 51, 3133
29. -1) 1760. See: Woulfe, S. R.; Miller, M. J. J. Org. Chem. 1986, 51, 3133
30. -1) 1760. See: Woulfe, S. R.; Miller, M. J. J. Org. Chem. 1986, 51, 3133
31. Marcantoni, E.; Alessandrini, S.; Malavolta, M.; Bartoli, G.; Bellucci, M. C.; Sambri, L.; Dalpozzo, R. J. Org. Chem. 1999, 64, 1986.
32. The syn relative stereochemistry of compund 18 was expected on the basis of the chelation control. The assignment was based on the values of melting point observed, 153-154 °C (lit. mp 153.2-153.4 °C): Bänzinger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010. The melting point reported for the anti isomer is 187.5 °C: Rich, D.; Sun, D. H.; Edgar, U. J. Med. Chem. 1980, 23, 27.
33. The syn relative stereochemistry of compund 18 was expected on the basis of the chelation control. The assignment was based on the values of melting point observed, 153-154 °C (lit. mp 153.2-153.4 °C): Bänzinger, M.; McGarrity, J. F.; Meul, T. J. Org. Chem. 1993, 58, 4010. The melting point reported for the anti isomer is 187.5 °C: Rich, D.; Sun, D. H.; Edgar, U. J. Med. Chem. 1980, 23, 27.
34. 3) δ 178.7, 156.4, 141.3, 128.7, 127.4, 125.8, 71.7, 59.8, 48.6, 39.8, 31.7, 24.1.
35. 13C NMR and mass spectrometry (ES/MS).