An unexpected Mitsunobu reaction. A direct route to the 2,5-diazabicyclo[2.2.1]heptan-3-one skeleton as a γ-lactam mimic of β-lactam antibiotics

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 4, 1997, Pages 503-509

  Hadfield, Peter S ^a   Galt, Ron H B ^b   Sawyer, Yvonne ^b   Layland, Nicola J ^a   Page, Michael I ^a  

^a UNIVERSITY OF HUDDERSFIELD   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748658255     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a604564b     Document Type: Article

References (22)

1. J. L. Strominger, Antibiotics (NY), 1967, 1, 706;
2. R. B. Woodward, in The Chemistry of Penicillin, ed. H. T. Clarke, J. R. Johnson and R. Robinson, Princeton University Press, Princeton, New Jersey, 1949, p. 443.
3. M. I. Page, in The Chemistry of β-Lactams, ed. M. I. Page, Blackie, Glasgow, 1992, pp. 79-100;
4. M. I. Page, Acc. Chem. Res., 1984, 17, 144.
5. N. C. Cohen, J. Med. Chem., 1983, 26, 259;
6. D. R. Boyd, C. Eigenbrot, J. M. Indelicato, M. M. Miller, C. E. Pasini and S. R. Woulfe, J. Med. Chem., 1987, 30, 528.
7. J. Mavchand-Brynaert and L. Ghosez, in Recent Progress in the Chemical Synthesis of Antibiotics, ed. M. Ohno and G. Lukais, Springer-Verlag, Berlin, 1990, pp. 729-794;
8. J. E. Baldwin, G. P. Lynch and J. Pitlik. J. Antibiot., 1991, 44, 1.
9. L. N. Jungheim and R. J. Ternansky, in The Chemistry of β-Lactams, ed. M. I. Page, Blackie, Glasgow, 1992, pp. 306-324.
10. L. N. Jungheim, D. B. Boyd, J. M. Indelicato, C. E. Pasini, D. A. Preston and W. E. Alborn, Jr., J. Med. Chem., 1991, 34, 1732.
11. J. Marchand-Brynaert, Z. Bounkhala-Khrouz, J. C. Carretero, J. Davies, D. Ferroud, B. J. van Keulen, B. Serckx-Poncin and L. Ghosez, in Recent Advances in the Chemistry of β-Lactam Antibiotics, ed. P. H. Bentley and R. Southgate, Royal Society of Chemistry, London, 1989, pp. 157-170.
12. J. E. Baldwin, C. Lowe and C. J. Schofield, Tetrahedron Lett., 1990, 31, 2211.
13. J. Marchand-Brynaert, E. Amadei and L. Ghosez, Bull. Soc. Chim. Belg., 1994, 103, 213.
14. O. Mitsunobu, Synthesis, 1981, 1.
15. E. Grochowski, B. D. Hilton, R. J. Kupper and C. J. Michejda, J. Am. Chem. Soc, 1982, 104, 6876.
16. Sumitomo Chemical Co. Ltd., Japan, EP 0 126 587/1984.
17. D. J. Abraham, M. Mokotoff, L. Sheh and J. E. Simmons, J. Med. Chem., 1983, 26, 549;
18. R. H. Andreatta, V. Nair, A. V. Robertson and W. R. J. Simpson, Aust. J. Chem., 1967, 20, 1493.
19. D. Seebach, Angew. Chem., Int. Ed. Engl., 1990, 29, 1320;
20. T. A. Alston, D. J. T. Porter and H. J. Bright, Acc. Chem. Res., 1983, 16, 418.
21. J. Jones, in Amino Acid and Peptide Synthesis, ed. S. G. Davies, Oxford Chemistry Primers, Oxford, Science Publ., 1992, p. 31.
22. S. G. Waley, in The Chemistry of β-Lactams, ed. M. I. Page, Chapman and Hall, London, 1992, pp. 198-228.