Synthesis of a 3-keto bicyclic pyrazolidinone using a Curtius rearrangement

Tetrahedron Letters

Volumn 37, Issue 28, 1996, Pages 4891-4894

  Neel, David A ^a   Holmes, Richard E ^a   Paschal, Jonathan W ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; CARBACEPHEM DERIVATIVE; CARBAPENEM DERIVATIVE; GAMMA LACTAM DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; HYDROLYSIS; PH; POLYMERIZATION;

EID: 0030575360     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01003-9     Document Type: Article

References (14)

1. 1. (a) Jungheim, L. N.; Sigmund, S. K.; J. Org. Chem. 1987, 52, 4007-13.
2. (b) Jungheim, L. N.; Ternansky, R, J.; Holmes, R. E.; Drugs of the Future 1990, 15, 149-157.
3. 2. Ternansky, R. J.; Drahein, S. E.; Pike, A. J.; Ott, J. L.; "Pyrazolidinone Antibacterial Agents, Synthesis and In Vitro Activity of New, Highly Potent Analogues. "XXVII Interscience Conference on Antimicrobial Agents and Chemotherapy, Abstract #1213, 1987.
4. 3. (a) Ratliffe, R. W. ; Salzmann, T. N.; Christensen, B. G.; Tetrahedron Lett. 1980, 21, 31-34.
5. (b) Evans, D. A. ; Sjogren, E. B.; Tetrahedron Lett. 1985, 26, 3787-90.
6. (c) Hashiguchi, S.; Natsugari, H.; Ochiai, M.; J. Chem. Soc. Perkin Trans. 1 1988, 2345-52.
7. 4. Hatanaka, M.; Yamamoto, Y.; Nitta, H.; Ishimaru, T.; Tetrahedron Lett. 1981, 22, 3883-86.
8. 2tBu/NaH. Hydrogenation and DCC/HBT coupling with PhSH gave the thiol ester.
9. 6. Spry, D. O.; J. Chem. Soc. Chem. Commun. 1974, 1012-13.
10. 7. During the course of this work an asymetric synthesis of 8 was accomplished. Holmes, R. E.; Neel, D. A.; Tetrahedron Lett. 1990, 31, 5567-70.
11. 8. Ternansky, R. J.; Draheim, S. E.; Tetrahedron Lett. 1990, 31, 2805-2808.
12. 9. (a) Taylor, E. C.; Shvo, Y.; J. Org. Chem. 1968, 33, 1719-27.
13. (b) deSolms, S. J.; J. Org. Chem. 1976, 41, 2650-51.
14. 6: C, 54.07; H, 7.09; N, 11.82. Found: C, 54.31; H, 7.26; N, 11.78.