Novel functionalized acylphosphonates as phosphonoformate analogs

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 7212-7216

  Glabe, Alan R ^a   Sturgeon, Katherine L ^a   Ghizzoni, Sally B ^a   Musker, W Kenneth ^a   Takahashi, Joyce N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000624826     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9611834     Document Type: Article

References (36)

1. (a) Sundquist, B.; Oberg, B. J. Gen. Virol. 1979, 45, 273-281.
2. (b) Richman, D. D. In Design of Anti-AIDS Drugs; De Clerq, E., Ed.; Eisevier Science: Netherlands, 1990; p 351.
3. Seidel, E. A.; Koenig, S.; Polis, M. A. AIDS 1993, 7, 941-945.
4. (a) Iyer, R. P.; Phillips, L. R.; Biddle, J. A.; Thakker, D. R.; Egan, W. Tetrahedron Lett. 1989, 30, 7141-7144.
5. (b) Neto, C. C.; Stein, J. M.; Sarin, P. S.; Sun, D. K.; Bhongle, N. N.; Piralta, R. K.; Turcotte, J. G. Biochem. Biophys. Res. Commun. 1990, 1, 458-463.
6. 12-18 primer-template concentration should be nM instead of mM.
7. (a) Larder, B. A.; Purifoy, D. J. M.; Powell, K. L.; Darby, G. Nature 1987, 327, 716-717.
8. (b) Fersht, A. Enzyme Structure and Mechanism, 2nd ed.; W. H. Freeman and Co.: New York, 1985; pp 252-253.
9. (c) Fersht, A. Enzyme Structure and Mechanism, 2nd ed.; W. H. Freeman and Co.: New York, 1985; pp 422-423.
10. (a) Emsley, J.; Hall, D. Chemistry of Phosphorus; Harper and Row: London, 1976; pp 117-119.
11. (b) Gerrard, W.; Green, W. J. J. Chem. Soc. 1951, 2250-2253.
12. (c) Corbridge, D. E. C. Phosphorus: An Outline of its Chemistry, Biochemistry and Technology, 4th ed.; Elsevier Science Publishers Co., Inc.: New York, 1990.
13. (d.) Arbuzov, A. E.; Kamay, G. X.; Belorossova, O. N. J. Gen. Chem. 1945, 15, 766.
14. (e) Britteli, D. R. J. Org. Chem. 1985, 50, 1845.
15. (a) Dixon, H.; Sparkes, M. Biochem. J. 1991, 272, 767.
16. (b) Karaman, R.; Goldblum, A.; Breuer, E. J. Chem. Soc., Perkin Trans. 1 1989, 765-774.
17. Wissner, A.; Grudzinskas, C. V. J. Org. Chem. 1978, 43, 3972.
18. Corey, E. J.; Ponder, J. W.; Ulrich, P. Tetrahedron Lett. 1980, 21, 137.
19. (a) Sprecher, M.; Nativ, E. Tetrahedron Lett. 1968, 42, 4405-4408.
20. (b) Quin, L. D.; Kislaus, J. C.; Mesch, K. A. J. Org. Chem. 1983, 48, 4466-4472.
21. (c) Gordon, N. J.; Evans, S. A. J. Org. Chem. 1993, 58, 4516-4519.
22. (a) Adam, W.; Curci, R.; Edwards, E. Acc. Chem. Res. 1989, 22, 205-211.
23. (b) Adam, W.; Hadjiarapoglou, L.; Nestler, B. Tetrahedron Lett. 1990, 31, 331-334.
24. (c) Murray, R. W.; Jeyaraman, R. J. Org. Chem. 1985, 50, 2847-2853.
25. Singh, S. P.; Kagan, J. J. Org. Chem. 1970, 35, 3839.
26. McKenna, C. E.; Higa, M. T.; Cheung, N. H.; McKenna, M.-C. Tetrahedron Lett. 1977, 2, 155-8.
27. (a) Guss, C. O. J. Org. Chem. 1952, 17, 678-682.
28. (b) Guss, C. O.; Rosenthal, R. J. Am. Chem. Soc. 1955, 2549.
29. Larcheveque, M.; Petit, Y. Tetrahedron Lett. 1987, 28, 1993-1996.
30. Chrzanowski, R. L.; Han, J. C.-Y.; McIntosh, C. L. J. Agric. Food Chem. 1979, 27, 550-4.
31. Sekine, M.; Okimoto, K.; Yamada, K.; Hata, T. J. Org. Chem. 1981, 46, 2097.
32. Danishefsky, S.; Zamboni, R.; Kahn, M.; Etheredge, S. J. J. Am. Chem. Soc. 1981, 103, 3460-3467.
33. Miyano, M. J. Am. Chem. Soc. 1965, 87, 3958-3962.
34. (a) Izumiya, N. Bull. Chem. Soc. Jpn. 1953, 26, 53-56.
35. (b) Shimohigashi, Y.; Waki, M.; Izumiya, N. Bull. Chem. Soc. Jpn. 1977, 52, 949-950.
36. Plattner, J.; Gless, R.; Rapoport, H. J. Am. Chem. Soc. 1972, 94, 8613-8615.