C4,C4′-bis-β-lactam to fused bis-γ-lactam rearrangement

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9156-9163

  Alcaide, Benito ^a   Martín Cantalejo, Yolanda ^a   Pérez Castells, Javier ^a,b   Sierra, Miguel A ^a   Monge, Angeles ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSIDAD SAN PABLO CEU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE;

ARTICLE; DRUG PURITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030471631     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960826c     Document Type: Article

References (44)

1. See, for example: Ojima, I. The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH Publishers: New York, 1993; pp 197.
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3. Some recent references: (a) Ojima, I.; Ng, E. W.; Sun, C. M. Tetrahedron Lett. 1995, 36, 4547. (b) Palomo, C.; Aizpurua, J. M.; Urchegui, R.; García, J, M. J. Chem. Soc., Chem. Commun. 1995, 2327. (c) Abouabdellah, A.; Welch, J. T. Tetrahedron: Asymmetry 1994, 5, 1005. (d) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Maneiro, E.; Odriozola, B. J. Chem. Soc., Chem. Commun. 1994, 1505. (e) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Carreux, F.; Cuevas, C.; Maneiro, E.; Ontoria, J. M. J. Org. Chem. 1994, 59, 3123.
4. Some recent references: (a) Ojima, I.; Ng, E. W.; Sun, C. M. Tetrahedron Lett. 1995, 36, 4547. (b) Palomo, C.; Aizpurua, J. M.; Urchegui, R.; García, J, M. J. Chem. Soc., Chem. Commun. 1995, 2327. (c) Abouabdellah, A.; Welch, J. T. Tetrahedron: Asymmetry 1994, 5, 1005. (d) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Maneiro, E.; Odriozola, B. J. Chem. Soc., Chem. Commun. 1994, 1505. (e) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Carreux, F.; Cuevas, C.; Maneiro, E.; Ontoria, J. M. J. Org. Chem. 1994, 59, 3123.
5. Some recent references: (a) Ojima, I.; Ng, E. W.; Sun, C. M. Tetrahedron Lett. 1995, 36, 4547. (b) Palomo, C.; Aizpurua, J. M.; Urchegui, R.; García, J, M. J. Chem. Soc., Chem. Commun. 1995, 2327. (c) Abouabdellah, A.; Welch, J. T. Tetrahedron: Asymmetry 1994, 5, 1005. (d) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Maneiro, E.; Odriozola, B. J. Chem. Soc., Chem. Commun. 1994, 1505. (e) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Carreux, F.; Cuevas, C.; Maneiro, E.; Ontoria, J. M. J. Org. Chem. 1994, 59, 3123.
6. Some recent references: (a) Ojima, I.; Ng, E. W.; Sun, C. M. Tetrahedron Lett. 1995, 36, 4547. (b) Palomo, C.; Aizpurua, J. M.; Urchegui, R.; García, J, M. J. Chem. Soc., Chem. Commun. 1995, 2327. (c) Abouabdellah, A.; Welch, J. T. Tetrahedron: Asymmetry 1994, 5, 1005. (d) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Maneiro, E.; Odriozola, B. J. Chem. Soc., Chem. Commun. 1994, 1505. (e) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Carreux, F.; Cuevas, C.; Maneiro, E.; Ontoria, J. M. J. Org. Chem. 1994, 59, 3123.
7. Some recent references: (a) Ojima, I.; Ng, E. W.; Sun, C. M. Tetrahedron Lett. 1995, 36, 4547. (b) Palomo, C.; Aizpurua, J. M.; Urchegui, R.; García, J, M. J. Chem. Soc., Chem. Commun. 1995, 2327. (c) Abouabdellah, A.; Welch, J. T. Tetrahedron: Asymmetry 1994, 5, 1005. (d) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Maneiro, E.; Odriozola, B. J. Chem. Soc., Chem. Commun. 1994, 1505. (e) Palomo, C.; Aizpurua, J. M.; Gamboa, I.; Carreux, F.; Cuevas, C.; Maneiro, E.; Ontoria, J. M. J. Org. Chem. 1994, 59, 3123.
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14. Some selected references: (a) Thomas, E. J.; Williams, A. S. J. Chem. Soc, Perkin Trans. 1 1995, 351. (b) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W. Tetrahedron 1995, 51, 5169. (c) Van Hove, F.; Vanwetswinkel, S.; Marchand-Brynaert, J.; Fastrez, J. Tetrahedron Lett. 1995, 36, 9313. (d) Baldwin, J. E.; Adlington, R. M.; Elend, A. S.; Smith, M. L. Tetrahedron 1995, 51, 11581. (e) Li, X.; Niu, C.; Miller, M. J. Tetrahedron Lett. 1995, 36, 1617.
15. Some selected references: (a) Thomas, E. J.; Williams, A. S. J. Chem. Soc, Perkin Trans. 1 1995, 351. (b) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W. Tetrahedron 1995, 51, 5169. (c) Van Hove, F.; Vanwetswinkel, S.; Marchand-Brynaert, J.; Fastrez, J. Tetrahedron Lett. 1995, 36, 9313. (d) Baldwin, J. E.; Adlington, R. M.; Elend, A. S.; Smith, M. L. Tetrahedron 1995, 51, 11581. (e) Li, X.; Niu, C.; Miller, M. J. Tetrahedron Lett. 1995, 36, 1617.
16. Some selected references: (a) Thomas, E. J.; Williams, A. S. J. Chem. Soc, Perkin Trans. 1 1995, 351. (b) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W. Tetrahedron 1995, 51, 5169. (c) Van Hove, F.; Vanwetswinkel, S.; Marchand-Brynaert, J.; Fastrez, J. Tetrahedron Lett. 1995, 36, 9313. (d) Baldwin, J. E.; Adlington, R. M.; Elend, A. S.; Smith, M. L. Tetrahedron 1995, 51, 11581. (e) Li, X.; Niu, C.; Miller, M. J. Tetrahedron Lett. 1995, 36, 1617.
17. Some selected references: (a) Thomas, E. J.; Williams, A. S. J. Chem. Soc, Perkin Trans. 1 1995, 351. (b) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W. Tetrahedron 1995, 51, 5169. (c) Van Hove, F.; Vanwetswinkel, S.; Marchand-Brynaert, J.; Fastrez, J. Tetrahedron Lett. 1995, 36, 9313. (d) Baldwin, J. E.; Adlington, R. M.; Elend, A. S.; Smith, M. L. Tetrahedron 1995, 51, 11581. (e) Li, X.; Niu, C.; Miller, M. J. Tetrahedron Lett. 1995, 36, 1617.
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21. (a) Alcaide, B.; Pérez-Castells, J.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1995, 60, 6012.
22. (b) Alcaide, B.; Martín-Cantalejo, Y.; Rodríguez-López, J.; Sierra, M. A. J. Org. Chem. 1993, 58, 4767.
23. Alcaide, B.; Martín-Cantalejo, Y.; Pérez-Castells, J.; Rodríguez-López, J.; Sierra, M. A.; Monge, A.; Pérez-García, V. J. Org. Chem. 1992, 57, 5921.
24. (a) Lin, G.-q.; Shi, Z.-c. Tetrahedron Lett. 1995, 36, 9537.
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26. (b) Klaus, R.; Wolfhard, E.; Wolfgang, E.; Guenter, T.; Gerhard, M.; Heri, D.; Norbert, M. Ger. Offen. DE 3930266; Chem. Abstr. 1991, 115, 71659a.
27. (a) Cossio, F. P.; Arrieta, A.; Lecea, B.; Ugalde, J. M. J. Am. Chem. Soc. 1994, 116, 2085. The chiral outcome of the model proposed has been applied succesfully to our systems in this paper.
28. (b) Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 116, 5784.
29. Merz, A. Angew. Chem., Int. Ed. Engl. 1973, 12, 846.
30. The stereochemical outcome of β-lactams derived from D-glyceraldehyde acetonide has been determined both experimental and theoretically. For the experimental approach, see: (a) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (b) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (c) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein. For the theoretical approach see, ref 12a.
31. The stereochemical outcome of β-lactams derived from D-glyceraldehyde acetonide has been determined both experimental and theoretically. For the experimental approach, see: (a) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (b) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (c) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein. For the theoretical approach see, ref 12a.
32. The stereochemical outcome of β-lactams derived from D-glyceraldehyde acetonide has been determined both experimental and theoretically. For the experimental approach, see: (a) Hubschwerelen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (b) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (c) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227 and references therein. For the theoretical approach see, ref 12a.
33. This sequential approach was initially reported by Bose to prepare racemic C4,C4′-bis-β-lactams starting from racemic aldehydes analogous to 4 . However, the overall yields reported in Bose's work are very low. See: Bose, A. K.; Womelsdorf, J. F.; Krishnan, L.; Urbanczyk-Lipkowska, Z.; Shelly, D. C.; Manhas, M. Tetrahedron 1991, 47, 5379.
34. In this work trans,trans and trans,cis notation in γ-lactams will refer to the relative orientation of the hydrogens attached to positions C1-C8 and C4-C5, with the hydrogens of the fusion (C1-C5) always having a cis orientation.
35. This influence of the group attached to the lactam nitrogen on the reactivity of the four-membered ring is well-known in β-lactam chemistry. Thus, groups inhibitors of the amide resonance render the 2-azetidinone prone to ring opening and make the carbonyl group proclive to nucleophile addition. See, among others: (a) Baldwin, J. E.; Edwards, J. E.; Farthing, C. N.; Russell, A. T. Synlett 1993, 49. (b) Kawamura, Y.; Sanemitsu, Y. J. Org. Chem. 1993, 58, 414.
36. This influence of the group attached to the lactam nitrogen on the reactivity of the four-membered ring is well-known in β-lactam chemistry. Thus, groups inhibitors of the amide resonance render the 2-azetidinone prone to ring opening and make the carbonyl group proclive to nucleophile addition. See, among others: (a) Baldwin, J. E.; Edwards, J. E.; Farthing, C. N.; Russell, A. T. Synlett 1993, 49. (b) Kawamura, Y.; Sanemitsu, Y. J. Org. Chem. 1993, 58, 414.
37. In these reaction conditions a 10% of trans,trans-C4,C4′-bis-β-lactam 1l was obtained. See Experimental Section.
38. Alcaide, B; Esteban, G.; Martíri-Cantalejo, Y.; Plumet, J.; Rodríguez-López, J.; Monge, A.; Pérez-García, V. J. Org. Chem. 1994, 59, 7994.
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40. (b) Kliegman, J. M.; Barnes, R. K. Tetrahedron 1970, 26, 2555.
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43. Jarayaman, M.; Deshmukh, A. R.-A. S.; Bhawal, B. M. J. Org. Chem. 1994, 59, 5921.
44. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.