Free radical reactions for heterocycle synthesis: Formation of keto spiro-γ-lactones and keto spiro-γ-lactams

Tetrahedron Letters

Volumn 40, Issue 43, 1999, Pages 7595-7598

  Zhang, Wei ^a   Pugh, Georgia ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID; ESTER DERIVATIVE; FREE RADICAL; GAMMA LACTAM DERIVATIVE; GAMMA LACTONE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; MOLECULAR INTERACTION;

EID: 0033595856     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01543-9     Document Type: Article

References (21)

1. Recent publications on spirolactone synthesis: (a) Carda, M.; Castillo, E.; Rodriguez, S.; Falomira, E.; Marco, J. A. Tetrahedron Lett. 1998, 39, 8895.
2. (b) Paruch, E.; Ciunik, Z.; Wawrzenczyk, C. Eur. J. Org. Chem. 1998, 11, 2677.
3. (c) Taylor, S. K.; Chmiel, N. H.; Mann, E. E.; Silver, M. E.; Vyvyan, J. R. Synthesis 1998, 1009.
4. (d) Clive, D. L. J.; Coltart, D. M. Tetrahedron Lett. 1998, 39, 2519.
5. (e) Clive, D. L. J.; Zhou, Y.; de Lima, D. P. J. Chem. Soc., Chem. Commun. 1996, 1463.
6. (f) Pellissier, H.; Michellys, P.-Y.; Santelli, M. J. Org. Chem. 1997, 62, 5588.
7. (g) Back, T. G.; Gladstone, P. L.; Parvez, M. J. Org. Chem. 1996, 62, 3806.
8. (h) Rieke, R. D.; Sell, M. S.; Xiong, H. J. Org. Chem. 1995, 60, 5143.
9. Radical cyclization of enol esters and enol ethers: (a) Ladlow, M.; Pattenden, G. Tetrahedron Lett. 1984, 25, 4317.
10. (b) Lee, E.; Tae, J. S.; Lee, C.; Park, C. M. Tetrahedron Lett. 1993, 34, 4831.
11. (c) Evans, P. A.; Roseman, J. D. Tetrahedron Lett. 1995, 36, 31.
12. Ragan, J. A.; Makowski, T. W.; Ende, D. J.; Clifford, P. J.; Young, G. R.; Conrad, A. K.; Eisenbeis, S. A. Org. Process Research and Development 1998, 379.
13. 13C NMR, MS, and IR analyses.
14. (a) Ashimori, A.; Overman, L. E. J. Org. Chem. 1992, 57, 4571.
15. (b) Abelman, M. M.; Overman, L. E. J. Org. Chem. 1987, 52, 4130.
16. (c) Grigg, R.; Putnikovic, B.; Urch, C. J. Tetrahedron Lett. 1996, 37, 695.
17. (a) Cossy, J.; Cases, M.; Pardo, D. G. Tetrahedron Lett. 1998, 39, 2331.
18. (b) Cabri, W.; Candiai, I.; Colombo, M.; Franzoi, L.; Bedeschi, A. Tetrahedron Lett. 1995, 36, 949.
19. (c) Hart, D.; Wu, S. C. Tetrahedron Lett. 1991, 32, 4099.
20. (d) Takano, S.; Suzuki, M.; Kijima, A.; Ogasawara, K. Tetrahedron Lett. 1990, 31, 2315.
21. (e) Jones, K.; Thompson, M.; Wright, C. J. Chem. Soc., Chem. Commun. 1986, 115.