The intramolecular aldol condensation route to fused Bi- and tricyclic β-lactams 1,2

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 7125-7132

  Alcaide, Benito ^a   Polanco, Concepción ^a   Sáez, Elena ^a   Sierra, Miguel A ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0029822636     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960904w     Document Type: Article

References (41)

1. This paper is respectfully dedicated to the Memory of Professor Francisco Farina.
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8. Carbapenems: (a) Palomo, C. In Recent Progress In the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin-Heidelberg, 1990; pp 565-612. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A., Ed.; Eisevier Science: Amsterdam, 1989; Vol. 4, p 431. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Berks, A. H. Tetrahedron 1996, 52, 331. Carbacefems: (e) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. Tribactams: (f) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. J. Chem. Soc., Chem. Commun. 1995, 661. (g) Pavoda, A.; Roberts, S. M.; Donati, D.; Perboni, A.; Rossi, T. J. Chem. Soc., Chem. Commun. 1994, 441. (h) Bismara, C.; Di Fabio, R.; Donati, D.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. (i) Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 9604. (j) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. Tetrahedron 1996, 52, 263.
9. Carbapenems: (a) Palomo, C. In Recent Progress In the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin-Heidelberg, 1990; pp 565-612. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A., Ed.; Eisevier Science: Amsterdam, 1989; Vol. 4, p 431. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Berks, A. H. Tetrahedron 1996, 52, 331. Carbacefems: (e) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. Tribactams: (f) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. J. Chem. Soc., Chem. Commun. 1995, 661. (g) Pavoda, A.; Roberts, S. M.; Donati, D.; Perboni, A.; Rossi, T. J. Chem. Soc., Chem. Commun. 1994, 441. (h) Bismara, C.; Di Fabio, R.; Donati, D.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. (i) Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 9604. (j) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. Tetrahedron 1996, 52, 263.
10. Carbapenems: (a) Palomo, C. In Recent Progress In the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin-Heidelberg, 1990; pp 565-612. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A., Ed.; Eisevier Science: Amsterdam, 1989; Vol. 4, p 431. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Berks, A. H. Tetrahedron 1996, 52, 331. Carbacefems: (e) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. Tribactams: (f) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. J. Chem. Soc., Chem. Commun. 1995, 661. (g) Pavoda, A.; Roberts, S. M.; Donati, D.; Perboni, A.; Rossi, T. J. Chem. Soc., Chem. Commun. 1994, 441. (h) Bismara, C.; Di Fabio, R.; Donati, D.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. (i) Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 9604. (j) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. Tetrahedron 1996, 52, 263.
11. Carbapenems: (a) Palomo, C. In Recent Progress In the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin-Heidelberg, 1990; pp 565-612. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A., Ed.; Eisevier Science: Amsterdam, 1989; Vol. 4, p 431. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Berks, A. H. Tetrahedron 1996, 52, 331. Carbacefems: (e) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. Tribactams: (f) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. J. Chem. Soc., Chem. Commun. 1995, 661. (g) Pavoda, A.; Roberts, S. M.; Donati, D.; Perboni, A.; Rossi, T. J. Chem. Soc., Chem. Commun. 1994, 441. (h) Bismara, C.; Di Fabio, R.; Donati, D.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. (i) Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 9604. (j) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. Tetrahedron 1996, 52, 263.
12. Carbapenems: (a) Palomo, C. In Recent Progress In the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin-Heidelberg, 1990; pp 565-612. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A., Ed.; Eisevier Science: Amsterdam, 1989; Vol. 4, p 431. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Berks, A. H. Tetrahedron 1996, 52, 331. Carbacefems: (e) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. Tribactams: (f) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. J. Chem. Soc., Chem. Commun. 1995, 661. (g) Pavoda, A.; Roberts, S. M.; Donati, D.; Perboni, A.; Rossi, T. J. Chem. Soc., Chem. Commun. 1994, 441. (h) Bismara, C.; Di Fabio, R.; Donati, D.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. (i) Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 9604. (j) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. Tetrahedron 1996, 52, 263.
13. Carbapenems: (a) Palomo, C. In Recent Progress In the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin-Heidelberg, 1990; pp 565-612. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A., Ed.; Eisevier Science: Amsterdam, 1989; Vol. 4, p 431. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Berks, A. H. Tetrahedron 1996, 52, 331. Carbacefems: (e) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. Tribactams: (f) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. J. Chem. Soc., Chem. Commun. 1995, 661. (g) Pavoda, A.; Roberts, S. M.; Donati, D.; Perboni, A.; Rossi, T. J. Chem. Soc., Chem. Commun. 1994, 441. (h) Bismara, C.; Di Fabio, R.; Donati, D.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. (i) Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 9604. (j) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. Tetrahedron 1996, 52, 263.
14. Carbapenems: (a) Palomo, C. In Recent Progress In the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin-Heidelberg, 1990; pp 565-612. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A., Ed.; Eisevier Science: Amsterdam, 1989; Vol. 4, p 431. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Berks, A. H. Tetrahedron 1996, 52, 331. Carbacefems: (e) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. Tribactams: (f) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. J. Chem. Soc., Chem. Commun. 1995, 661. (g) Pavoda, A.; Roberts, S. M.; Donati, D.; Perboni, A.; Rossi, T. J. Chem. Soc., Chem. Commun. 1994, 441. (h) Bismara, C.; Di Fabio, R.; Donati, D.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. (i) Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 9604. (j) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. Tetrahedron 1996, 52, 263.
15. Carbapenems: (a) Palomo, C. In Recent Progress In the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin-Heidelberg, 1990; pp 565-612. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A., Ed.; Eisevier Science: Amsterdam, 1989; Vol. 4, p 431. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Berks, A. H. Tetrahedron 1996, 52, 331. Carbacefems: (e) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. Tribactams: (f) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. J. Chem. Soc., Chem. Commun. 1995, 661. (g) Pavoda, A.; Roberts, S. M.; Donati, D.; Perboni, A.; Rossi, T. J. Chem. Soc., Chem. Commun. 1994, 441. (h) Bismara, C.; Di Fabio, R.; Donati, D.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. (i) Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 9604. (j) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. Tetrahedron 1996, 52, 263.
16. Carbapenems: (a) Palomo, C. In Recent Progress In the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin-Heidelberg, 1990; pp 565-612. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A., Ed.; Eisevier Science: Amsterdam, 1989; Vol. 4, p 431. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Berks, A. H. Tetrahedron 1996, 52, 331. Carbacefems: (e) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. Tribactams: (f) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. J. Chem. Soc., Chem. Commun. 1995, 661. (g) Pavoda, A.; Roberts, S. M.; Donati, D.; Perboni, A.; Rossi, T. J. Chem. Soc., Chem. Commun. 1994, 441. (h) Bismara, C.; Di Fabio, R.; Donati, D.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. (i) Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 9604. (j) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. Tetrahedron 1996, 52, 263.
17. Carbapenems: (a) Palomo, C. In Recent Progress In the Chemical Synthesis of Antibiotics; Lukacs, G., Ohno, M., Eds.; Springer-Verlag: Berlin-Heidelberg, 1990; pp 565-612. (b) Georg, G. I. In Studies in Natural Product Chemistry; Rahman, A., Ed.; Eisevier Science: Amsterdam, 1989; Vol. 4, p 431. (c) Nagahara, T.; Kametani, T. Heterocycles 1987, 25, 729. (d) Berks, A. H. Tetrahedron 1996, 52, 331. Carbacefems: (e) Cooper, R. D. G. In The Chemistry of β-Lactams; Page, M. I., Ed.; Chapman and Hall: London, 1992; Chapter 8. Tribactams: (f) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. J. Chem. Soc., Chem. Commun. 1995, 661. (g) Pavoda, A.; Roberts, S. M.; Donati, D.; Perboni, A.; Rossi, T. J. Chem. Soc., Chem. Commun. 1994, 441. (h) Bismara, C.; Di Fabio, R.; Donati, D.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1995, 36, 4283. (i) Rossi, T.; Biondi, S.; Contini, S.; Thomas, R. J.; Marchioro, C. J. Am. Chem. Soc. 1995, 117, 9604. (j) Pavoda, A.; Roberts, S. M.; Donati, D.; Marchioro, C.; Perboni, A. Tetrahedron 1996, 52, 263.
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31. The cis-selectivity obtained in the preparation of compounds 6-8 was the expected for the imines used according to the currently accepted mechanism of the Staüdinger reaction. See: (a) Dumas, S.; Hegedus, L. S. J. Org. Chem. 1994, 59, 4967. (b) Cossio, F. P.; Arrieta, A; Lecea, B; Ugalde, J. M. J. Am. Chem. Soc. 1995, 117, 9604.
32. Compounds through this paper are racemic. For clarity one diastereomer is always represented.
33. The trans-stereochemistry at the 2-azetidinone ring depicted in the Scheme 4 for tricycles 13/14 is based on the epimerization at the most acid center (the C3 position at the four membered ring) of the precursor monolactams. See ref. 19.
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38. See, for example: (a) Alcaide, B.; Domínguez, G.; Escobar, G.; Parreño, U.; Plumet, J. Heterocycles 1986, 24, 1579. (b) Manhas, M. S.; Ghosh, M.; Bose, A. K. J. Org. Chem. 1990, 55, 575. (c) Alcaide, B.; Martín-Cantalejo, Y.; Pérez-Castells, J.; Rodríguez-López, J.; Sierra, M. A. J. Org. Chem. 1992, 57, 5921.
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