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(b) Albers-Schönberg G., Arison B.H., Hensens O.D., Hirshfield J., Hoogsteen K., Kaczka E.A., Rhodes R.E., Kahan J.S., Kahan F.M., Ratcliffe R.W., Walton E., Ruswinkle L.J., Morin R.B., Patel G.S., Christensen B.G. J. Am. Chem. Soc. 100:1978;6491-6499.
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Eur. Pat. Appl. EP0416953 (cl. C07D477/00), March 13, 1991 235337t
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Tamburini, B.; Perboni, A.; Rossi, T.; Donati, D.; Andreotti, D.; Gaviraghi, G.; Carlesso R.; Bismara, C. Eur. Pat. Appl. EP0416953 (cl. C07D477/00), March 13, 1991; Chem. Abstr. 1992, 116, 235337t.
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The numbering of the bi- and tricyclic β-lactams is given according to the I.U.P.A.C. rules (Pure Appl. Chem. 1995, 67, 1307).
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Recent examples: (a) Hanessian S., Reddy B. Tetrahedron. 55:1999;3427-3443 (b) Alcaide B., Almendros P. Tetrahedron Lett. 40:1999;1015-1018 (c) Alcaide B., Polanco C., Sierra M.-A. J. Org. Chem. 63:1998;6786-6796 (d) Annibale A.D., Pesce A., Resta S., Trogolo C.T. Tetrahedron. 53:1997;13129-13138 (e) Alcaide B., Polanco C., Sáez E., Sierra M.-A. J. Org. Chem. 61:1996;7125-7132.
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Hanessian, S.1
Reddy, B.2
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Recent examples: (a) Hanessian S., Reddy B. Tetrahedron. 55:1999;3427-3443 (b) Alcaide B., Almendros P. Tetrahedron Lett. 40:1999;1015-1018 (c) Alcaide B., Polanco C., Sierra M.-A. J. Org. Chem. 63:1998;6786-6796 (d) Annibale A.D., Pesce A., Resta S., Trogolo C.T. Tetrahedron. 53:1997;13129-13138 (e) Alcaide B., Polanco C., Sáez E., Sierra M.-A. J. Org. Chem. 61:1996;7125-7132.
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Alcaide, B.1
Almendros, P.2
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9
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0032476127
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Recent examples: (a) Hanessian S., Reddy B. Tetrahedron. 55:1999;3427-3443 (b) Alcaide B., Almendros P. Tetrahedron Lett. 40:1999;1015-1018 (c) Alcaide B., Polanco C., Sierra M.-A. J. Org. Chem. 63:1998;6786-6796 (d) Annibale A.D., Pesce A., Resta S., Trogolo C.T. Tetrahedron. 53:1997;13129-13138 (e) Alcaide B., Polanco C., Sáez E., Sierra M.-A. J. Org. Chem. 61:1996;7125-7132.
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Alcaide, B.1
Polanco, C.2
Sierra, M.-A.3
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10
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0030864548
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Recent examples: (a) Hanessian S., Reddy B. Tetrahedron. 55:1999;3427-3443 (b) Alcaide B., Almendros P. Tetrahedron Lett. 40:1999;1015-1018 (c) Alcaide B., Polanco C., Sierra M.-A. J. Org. Chem. 63:1998;6786-6796 (d) Annibale A.D., Pesce A., Resta S., Trogolo C.T. Tetrahedron. 53:1997;13129-13138 (e) Alcaide B., Polanco C., Sáez E., Sierra M.-A. J. Org. Chem. 61:1996;7125-7132.
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Tetrahedron
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Annibale, A.D.1
Pesce, A.2
Resta, S.3
Trogolo, C.T.4
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11
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0029822636
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Recent examples: (a)
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Recent examples: (a) Hanessian S., Reddy B. Tetrahedron. 55:1999;3427-3443 (b) Alcaide B., Almendros P. Tetrahedron Lett. 40:1999;1015-1018 (c) Alcaide B., Polanco C., Sierra M.-A. J. Org. Chem. 63:1998;6786-6796 (d) Annibale A.D., Pesce A., Resta S., Trogolo C.T. Tetrahedron. 53:1997;13129-13138 (e) Alcaide B., Polanco C., Sáez E., Sierra M.-A. J. Org. Chem. 61:1996;7125-7132.
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Alcaide, B.1
Polanco, C.2
Sáez, E.3
Sierra, M.-A.4
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12
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0002488544
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Georg, G. I., Ed. Strategies for the Synthesis of Bicyclic β-Lactams; VCH: New York
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For a review on cyclization methodologies to prepare bicyclic (β-lactams, see: (a) Kant, J.; Walker, D. G.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams. Georg, G. I., Ed. Strategies for the Synthesis of Bicyclic β-Lactams; VCH: New York, 1993; pp 121-196. Recent examples to the synthesis of trinem derivatives: (b) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587-3590. (c) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463-468. (d) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884-9891.
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Kant, J.1
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13
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For a review on cyclization methodologies to prepare bicyclic (β-lactams, see: (a) Kant, J.; Walker, D. G.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams. Georg, G. I., Ed. Strategies for the Synthesis of Bicyclic β-Lactams; VCH: New York, 1993; pp 121-196. Recent examples to the synthesis of trinem derivatives: (b) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587-3590. (c) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463-468. (d) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884-9891.
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14
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33748659244
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For a review on cyclization methodologies to prepare bicyclic (β-lactams, see: (a) Kant, J.; Walker, D. G.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams. Georg, G. I., Ed. Strategies for the Synthesis of Bicyclic β-Lactams; VCH: New York, 1993; pp 121-196. Recent examples to the synthesis of trinem derivatives: (b) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587-3590. (c) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463-468. (d) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884-9891.
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Marchioro, C.1
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Donati, D.4
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For a review on cyclization methodologies to prepare bicyclic (β-lactams, see: (a) Kant, J.; Walker, D. G.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams. Georg, G. I., Ed. Strategies for the Synthesis of Bicyclic β-Lactams; VCH: New York, 1993; pp 121-196. Recent examples to the synthesis of trinem derivatives: (b) Di Fabio, R.; Rossi, T.; Thomas, R. J. Tetrahedron Lett. 1997, 38, 3587-3590. (c) Marchioro, C.; Pentassuglia, G.; Perboni, A.; Donati, D. J. Chem. Soc., Perkin Trans. 1 1997, 463-468. (d) Hanessian, S.; Rozema, M. J. J. Am. Chem. Soc. 1996, 118, 9884-9891.
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Martell S.R., Wisedale R., Gallager T., Hall L.D., Mahon M.F., Bradbury R.H., Hales N.J. J. Am. Chem. Soc. 119:1997;2309-2310.
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The preferred conformations for epoxides 4 were derived from the CS Chem3D Pro software (CambridgeSoft Corporation) using MM2 calculations
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The preferred conformations for epoxides 4 were derived from the CS Chem3D Pro software (CambridgeSoft Corporation) using MM2 calculations.
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32
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0001351921
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For a similar rearrangement from 4-formyl-2-azetidinones reacting with concentrated sulfuric acid see:
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For a similar rearrangement from 4-formyl-2-azetidinones reacting with concentrated sulfuric acid see: Alcaide B., Martín-Cantalejo Y., Rodríguez-López J., Sierra M.-A. J. Org. Chem. 58:1993;4767-4770.
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