Azabicyclo[3.2.0]heptan-7-ones (carbapenams) from pyrrole

Abstract

The azabicyclo[3.2.0]heptan-7-ones 4, 10, 16 and 24 have been prepared from pyrrole. The same general approach has been used for all these derivatives; namely, substitution of pyrrole at the 2- and 5-carbon atoms, catalytic hydrogenation to produce pyrrolidine-2-acetic acid derivatives, and cyclisation using tris(1,3-dihydro-2-oxobenzoxazol-3-yl)phosphine oxide 6. The catalytic hydrogenation of 2,5-disubstituted pyrroles gives only the corresponding cis-2,5-disubstituted pyrrolidines. The hydrogenation proceeds more easily when the nitrogen atom bears a tert-butoxycarbonyl substituent. The N-tert-butoxycarbonylpyrroles 8 and 21 bearing an α-substituent in the acetate side chain were hydrogenated with a high degree of facial stereoselectivity. This allowed the 6-phthalimidoazabicyclo[3.2.0]heptan-7-one 24 to be isolated as a single diastereoisomer. The X-ray crystal structure of a precursor, the triester, 22a, has been obtained.

References

1. F. Moll and H. Thoma, Z. Naturforsch. Teil B, 1969, 24, 942.
2. T. Nagasaka, A. Tsukada and F. Hamiguchi, Heterocycles, 1986, 24, 2015; T. Ohta, N. Sato, T. Kimura, S. Nozoe and K. Izawa, Tetrahedron Lett., 1988, 29, 4305; T. Ohta, S. Shiokawa, E. Iwashita, N. Sato, K. Sakurai, T. Ineyama, H. Izawa, K. Izawa and S. Nozoe, Heterocycles, 1992, 33, 143.
3. B. W. Bycroft and S. R. Chhabra, J. Chem. Soc., Chem. Commun., 1989, 423.
4. R. Busson and H. Vanderhaeghe, J. Org. Chem., 1978, 43, 4438; S. Asada, M. Kato, K. Asai, T. Ineyama, S. Nishi, K. Izawa and T. Shono, J. Chem. Soc., Chem. Commun., 1989, 486.
5. G. W. Gribble, in Comprehensive Organic Synthesis, ed. B. M. Trost and I. Fleming, vol. 8, ed. I. Fleming, Pergamon Press, Oxford, 1991, p. 603; M. Tokuda, Y. Yamada, T. Takagi and H. Suginome, Tetrahedron, 1987, 43, 281; D. R. Artis, I.-S. Cho, S. Jaime-Figueroa and J. M. Muchowski, J. Org. Chem., 1994, 59, 2456; C. W. Jefford, K. Sienkiewicz and S. R. Thornton, Tetrahedron Lett., 1994, 35, 4759; C. W. Jefford, K. Sienkiewicz and S. R. Thornton, Helv. Chim. Acta, 1995, 78, 1511.
6. H.-P. Kaiser and J. M. Muchowski, J. Org. Chem., 1984, 49, 4203.
7. M. Regitz, J. Hocker and A. Liedhegener, Org. Synth., Coll. Vol. V, 1973179.
8. E. Baciocchi, E. Muraglia and G. Sleiter, J. Org. Chem., 1992, 57, 6817.
9. G. C. Schloemer, R. Greenhouse and J. M. Muchowski, J. Org. Chem., 1994, 59, 5230.
10. T. Nagamatsu and T. Kunieda, Chem. Pharm. Bull., 1988, 36, 1249; T. Kunieda, T. Nagamatsu, T. Higuchi and M. Hirobe, Tetrahedron Lett., 1988, 29, 2203.
11. B. W. Bycroft, C. Maslen, S. J. Box, A. G. Brown and J. W. Tyler, J. Chem. Soc., Chem. Commun., 1987, 1623.
12. S. R. Berryhill, T. Price and M. Rosenblum, J. Org. Chem., 1983, 48, 158.
13. T. L. Gilchrist, K. Graham and S. Coulton, Tetrahedron Lett., 1995, 36, 8693.
14. T. L. Gilchrist and A. Lemos, J. Chem. Soc., Perkin Trans. 1, 1993, 1391.
15. A. T. Moore and H. N. Rydon, Org. Synth., Coll. Vol. V, 1973586.
16. C. J. Gilmore, MITHRIL, J. Appl. Crystallogr., 1984, 17, 42.
17. TEXSAN–TEXRAY Structure Analysis Package, Molecular Structure Corporation, 1985.