New developments in the enantioselective synthesis of cyclopentyl carbocyclic nucleosides

Tetrahedron

Volumn 54, Issue 32, 1998, Pages 9229-9272

  Crimmins, Michael T ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

9 [2,3 BIS(HYDROXYMETHYL)CYCLOBUTYL]ADENINE; ABACAVIR; ARISTEROMYCIN; CARBOCYCLIC NUCLEOSIDE; CARBOVIR; NEPLANOCIN A;

ACQUIRED IMMUNE DEFICIENCY SYNDROME; ANTINEOPLASTIC ACTIVITY; COUPLING FACTOR; DRUG SYNTHESIS; ENZYME PHOSPHORYLATION; NUCLEOTIDE METABOLISM; PRIORITY JOURNAL; PURINE SYNTHESIS; PYRIMIDINE SYNTHESIS; REVIEW; VIRUS LOAD;

EID: 0032490986     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00320-2     Document Type: Review

References (122)

1. 1. Mizuno, Y. In The Organic Chemistry of Nucleic Acids; Kadansha LTD: Tokyo (and Elsevier Science Amsterdam), 1986. Ueda, T. In Chemistry of Nucleosides and Nucleotides; Townsend, L.B., Ed.; Plenum Press: New York, 1988, Vol. 1, Chapter 1.
2. 1. Mizuno, Y. In The Organic Chemistry of Nucleic Acids; Kadansha LTD: Tokyo (and Elsevier Science Amsterdam), 1986. Ueda, T. In Chemistry of Nucleosides and Nucleotides; Townsend, L.B., Ed.; Plenum Press: New York, 1988, Vol. 1, Chapter 1.
3. 2. Srivasta, P.C.; Robins, R.K.; Meyer, R.B., Jr. In Chemistry of Nucleosides and Nucleotides; Townsend, L.B., Ed.; Plenum Press: New York, 1988, Vol. 1, Chapter 2. Revenkar, G.R.; Robins, R.K. In Chemistry of Nucleosides and Nucleotides; Townsend, L.B., Ed.; Plenum Press: New York, 1991, Vol. 2, Chapter 4.
4. 2. Srivasta, P.C.; Robins, R.K.; Meyer, R.B., Jr. In Chemistry of Nucleosides and Nucleotides; Townsend, L.B., Ed.; Plenum Press: New York, 1988, Vol. 1, Chapter 2. Revenkar, G.R.; Robins, R.K. In Chemistry of Nucleosides and Nucleotides; Townsend, L.B., Ed.; Plenum Press: New York, 1991, Vol. 2, Chapter 4.
5. 3. Borthwick, A.D.; Biggadike, K. Tetrahedron 1992, 48, 571-623.
6. 4. Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S.R.; Earl, R.A.; Guedj, R. Tetrahedron 1994, 50, 10611-10670.
7. 5. Huryn, D.; Okabe, M. Chem. Rev. 1992, 92, 1745-1768.
8. 6. Marquez, V.; Lim, M. Med. Res. Rev. 1986, 6, 1. Roberts, S.; Biggadike, K.; Borthwick, A.; Kirk, B. Topics in Medicinal Chemistry, E.d P.R., Royal Society of Chemistry, 1988, 172.
9. 6. Marquez, V.; Lim, M. Med. Res. Rev. 1986, 6, 1. Roberts, S.; Biggadike, K.; Borthwick, A.; Kirk, B. Topics in Medicinal Chemistry, E.d P.R., Royal Society of Chemistry, 1988, 172.
10. 7. Bricaud, H.; Hodewijn, P.; DeClerq, E. Biochem. Pharmacol. 1983, 3583.
11. 8. Shealy, Y.F.; Clayton, J.D. J. Am. Chem. Soc. 1966, 88, 3885-3887. Shealy, Y.F.; Clayton, J.D. J. Am. Chem. Soc. 1969, 91, 3075-3083. Shealy, Y.F.; Clayton, J.D. J. Pharm. Sci. 1973, 62, 1432.
12. 8. Shealy, Y.F.; Clayton, J.D. J. Am. Chem. Soc. 1966, 88, 3885-3887. Shealy, Y.F.; Clayton, J.D. J. Am. Chem. Soc. 1969, 91, 3075-3083. Shealy, Y.F.; Clayton, J.D. J. Pharm. Sci. 1973, 62, 1432.
13. 8. Shealy, Y.F.; Clayton, J.D. J. Am. Chem. Soc. 1966, 88, 3885-3887. Shealy, Y.F.; Clayton, J.D. J. Am. Chem. Soc. 1969, 91, 3075-3083. Shealy, Y.F.; Clayton, J.D. J. Pharm. Sci. 1973, 62, 1432.
14. 9. Kusaka, T.; Yamamoto, H.; Shibata, M.; Muroi, M.; Kishi, T.; Mizuno, K. J. Antibiot. 1968, 21, 255-271.
15. 10. Yaginuma, S.; Muto, N.; Tsujino, M.; Sudate, Y.; Hayashi, M.; Otani, M. J. Antibiot. 1981, 34, 359-366.
16. 11. Vince, R.; Hua, M. J. Med. Chem. 1999, 33, 17-21.
17. 12. "Therapeutic Nucleosides" Daluge, S.M. U.S. Patent 1991, patent number 5,034,394.
18. 13. Katagiri, N.; Nomura, M.; Sato, H.; Kaneko, C.; Yusa, K.; Tsuruo, T. J. Med. Chem. 1992, 35, 1882-1886.
19. 14. Daluge, S.M.; Good, S.S.; Martin, M.T.; Tibbels, S.R.; Miller, W.H.; Averett, D.R.; St. Clair, M.H.; Ayers, K.M. Abstracts of the 34th Interscience Conference on Antimicrobial Agents and Chemotherapy 1994, Abstract #16. Torres, G. GMHC Treatment Issues 1996, 10, 8. Saag, M. Abstracts from The Third Conference on Retroviruses and Opportunistic Infections, abstract 195. Kimberlin, D.W.; Coen, D.M.; Biron, K.K.; Cohen, J.I.; Lamb, R.A.; McKinlay, M.; Emini, E.A.; Whitley, R.J. Antiviral Res. 1995, 26, 369-401. Good, S.S.; Daluge, S.M.; Ching, S.V.; Ayers, K.M.; Mahony, W.B.; Faletto, M.B.; Domin, B.A.; Owens, B.S.; Dornsife, R.E.; McDowell, J.A.; LaFon, S.W.; Symonds, W.T. Antiviral Res. 1995, 26, A228. Daluge, S.M.; Good, S.S.; Faletto, M.B.; Miller, W.H.; St. Clair, M.H.; Boone, L.R; Tisdale, M.; Parry, N.R.; Reardon, J.E.; Dornsife, R.E.; Averett, D.R.; Krenitsky, T.A. Antimicrob. Agents Chem. 1997 41 1082-1093. Tisdale, M.; Alnadaf, T.; Cousens, D. Antimicrob. Agents Chem. 1997 41 1094-1098. Faletto, M.B.; Miller, W.H.; Garvey, E.P.; St. Clair, M.H.; Daluge, S.M.; Good, S.S. Antimicrob. Agents Chem. 1997 41 1099-1107.
20. 14. Daluge, S.M.; Good, S.S.; Martin, M.T.; Tibbels, S.R.; Miller, W.H.; Averett, D.R.; St. Clair, M.H.; Ayers, K.M. Abstracts of the 34th Interscience Conference on Antimicrobial Agents and Chemotherapy 1994, Abstract #16. Torres, G. GMHC Treatment Issues 1996, 10, 8. Saag, M. Abstracts from The Third Conference on Retroviruses and Opportunistic Infections, abstract 195. Kimberlin, D.W.; Coen, D.M.; Biron, K.K.; Cohen, J.I.; Lamb, R.A.; McKinlay, M.; Emini, E.A.; Whitley, R.J. Antiviral Res. 1995, 26, 369-401. Good, S.S.; Daluge, S.M.; Ching, S.V.; Ayers, K.M.; Mahony, W.B.; Faletto, M.B.; Domin, B.A.; Owens, B.S.; Dornsife, R.E.; McDowell, J.A.; LaFon, S.W.; Symonds, W.T. Antiviral Res. 1995, 26, A228. Daluge, S.M.; Good, S.S.; Faletto, M.B.; Miller, W.H.; St. Clair, M.H.; Boone, L.R; Tisdale, M.; Parry, N.R.; Reardon, J.E.; Dornsife, R.E.; Averett, D.R.; Krenitsky, T.A. Antimicrob. Agents Chem. 1997 41 1082-1093. Tisdale, M.; Alnadaf, T.; Cousens, D. Antimicrob. Agents Chem. 1997 41 1094-1098. Faletto, M.B.; Miller, W.H.; Garvey, E.P.; St. Clair, M.H.; Daluge, S.M.; Good, S.S. Antimicrob. Agents Chem. 1997 41 1099-1107.
21. 14. Daluge, S.M.; Good, S.S.; Martin, M.T.; Tibbels, S.R.; Miller, W.H.; Averett, D.R.; St. Clair, M.H.; Ayers, K.M. Abstracts of the 34th Interscience Conference on Antimicrobial Agents and Chemotherapy 1994, Abstract #16. Torres, G. GMHC Treatment Issues 1996, 10, 8. Saag, M. Abstracts from The Third Conference on Retroviruses and Opportunistic Infections, abstract 195. Kimberlin, D.W.; Coen, D.M.; Biron, K.K.; Cohen, J.I.; Lamb, R.A.; McKinlay, M.; Emini, E.A.; Whitley, R.J. Antiviral Res. 1995, 26, 369-401. Good, S.S.; Daluge, S.M.; Ching, S.V.; Ayers, K.M.; Mahony, W.B.; Faletto, M.B.; Domin, B.A.; Owens, B.S.; Dornsife, R.E.; McDowell, J.A.; LaFon, S.W.; Symonds, W.T. Antiviral Res. 1995, 26, A228. Daluge, S.M.; Good, S.S.; Faletto, M.B.; Miller, W.H.; St. Clair, M.H.; Boone, L.R; Tisdale, M.; Parry, N.R.; Reardon, J.E.; Dornsife, R.E.; Averett, D.R.; Krenitsky, T.A. Antimicrob. Agents Chem. 1997 41 1082-1093. Tisdale, M.; Alnadaf, T.; Cousens, D. Antimicrob. Agents Chem. 1997 41 1094-1098. Faletto, M.B.; Miller, W.H.; Garvey, E.P.; St. Clair, M.H.; Daluge, S.M.; Good, S.S. Antimicrob. Agents Chem. 1997 41 1099-1107.
22. 14. Daluge, S.M.; Good, S.S.; Martin, M.T.; Tibbels, S.R.; Miller, W.H.; Averett, D.R.; St. Clair, M.H.; Ayers, K.M. Abstracts of the 34th Interscience Conference on Antimicrobial Agents and Chemotherapy 1994, Abstract #16. Torres, G. GMHC Treatment Issues 1996, 10, 8. Saag, M. Abstracts from The Third Conference on Retroviruses and Opportunistic Infections, abstract 195. Kimberlin, D.W.; Coen, D.M.; Biron, K.K.; Cohen, J.I.; Lamb, R.A.; McKinlay, M.; Emini, E.A.; Whitley, R.J. Antiviral Res. 1995, 26, 369-401. Good, S.S.; Daluge, S.M.; Ching, S.V.; Ayers, K.M.; Mahony, W.B.; Faletto, M.B.; Domin, B.A.; Owens, B.S.; Dornsife, R.E.; McDowell, J.A.; LaFon, S.W.; Symonds, W.T. Antiviral Res. 1995, 26, A228. Daluge, S.M.; Good, S.S.; Faletto, M.B.; Miller, W.H.; St. Clair, M.H.; Boone, L.R; Tisdale, M.; Parry, N.R.; Reardon, J.E.; Dornsife, R.E.; Averett, D.R.; Krenitsky, T.A. Antimicrob. Agents Chem. 1997 41 1082-1093. Tisdale, M.; Alnadaf, T.; Cousens, D. Antimicrob. Agents Chem. 1997 41 1094-1098. Faletto, M.B.; Miller, W.H.; Garvey, E.P.; St. Clair, M.H.; Daluge, S.M.; Good, S.S. Antimicrob. Agents Chem. 1997 41 1099-1107.
23. 14. Daluge, S.M.; Good, S.S.; Martin, M.T.; Tibbels, S.R.; Miller, W.H.; Averett, D.R.; St. Clair, M.H.; Ayers, K.M. Abstracts of the 34th Interscience Conference on Antimicrobial Agents and Chemotherapy 1994, Abstract #16. Torres, G. GMHC Treatment Issues 1996, 10, 8. Saag, M. Abstracts from The Third Conference on Retroviruses and Opportunistic Infections, abstract 195. Kimberlin, D.W.; Coen, D.M.; Biron, K.K.; Cohen, J.I.; Lamb, R.A.; McKinlay, M.; Emini, E.A.; Whitley, R.J. Antiviral Res. 1995, 26, 369-401. Good, S.S.; Daluge, S.M.; Ching, S.V.; Ayers, K.M.; Mahony, W.B.; Faletto, M.B.; Domin, B.A.; Owens, B.S.; Dornsife, R.E.; McDowell, J.A.; LaFon, S.W.; Symonds, W.T. Antiviral Res. 1995, 26, A228. Daluge, S.M.; Good, S.S.; Faletto, M.B.; Miller, W.H.; St. Clair, M.H.; Boone, L.R; Tisdale, M.; Parry, N.R.; Reardon, J.E.; Dornsife, R.E.; Averett, D.R.; Krenitsky, T.A. Antimicrob. Agents Chem. 1997 41 1082-1093. Tisdale, M.; Alnadaf, T.; Cousens, D. Antimicrob. Agents Chem. 1997 41 1094-1098. Faletto, M.B.; Miller, W.H.; Garvey, E.P.; St. Clair, M.H.; Daluge, S.M.; Good, S.S. Antimicrob. Agents Chem. 1997 41 1099-1107.
24. 14. Daluge, S.M.; Good, S.S.; Martin, M.T.; Tibbels, S.R.; Miller, W.H.; Averett, D.R.; St. Clair, M.H.; Ayers, K.M. Abstracts of the 34th Interscience Conference on Antimicrobial Agents and Chemotherapy 1994, Abstract #16. Torres, G. GMHC Treatment Issues 1996, 10, 8. Saag, M. Abstracts from The Third Conference on Retroviruses and Opportunistic Infections, abstract 195. Kimberlin, D.W.; Coen, D.M.; Biron, K.K.; Cohen, J.I.; Lamb, R.A.; McKinlay, M.; Emini, E.A.; Whitley, R.J. Antiviral Res. 1995, 26, 369-401. Good, S.S.; Daluge, S.M.; Ching, S.V.; Ayers, K.M.; Mahony, W.B.; Faletto, M.B.; Domin, B.A.; Owens, B.S.; Dornsife, R.E.; McDowell, J.A.; LaFon, S.W.; Symonds, W.T. Antiviral Res. 1995, 26, A228. Daluge, S.M.; Good, S.S.; Faletto, M.B.; Miller, W.H.; St. Clair, M.H.; Boone, L.R; Tisdale, M.; Parry, N.R.; Reardon, J.E.; Dornsife, R.E.; Averett, D.R.; Krenitsky, T.A. Antimicrob. Agents Chem. 1997 41 1082-1093. Tisdale, M.; Alnadaf, T.; Cousens, D. Antimicrob. Agents Chem. 1997 41 1094-1098. Faletto, M.B.; Miller, W.H.; Garvey, E.P.; St. Clair, M.H.; Daluge, S.M.; Good, S.S. Antimicrob. Agents Chem. 1997 41 1099-1107.
25. 14. Daluge, S.M.; Good, S.S.; Martin, M.T.; Tibbels, S.R.; Miller, W.H.; Averett, D.R.; St. Clair, M.H.; Ayers, K.M. Abstracts of the 34th Interscience Conference on Antimicrobial Agents and Chemotherapy 1994, Abstract #16. Torres, G. GMHC Treatment Issues 1996, 10, 8. Saag, M. Abstracts from The Third Conference on Retroviruses and Opportunistic Infections, abstract 195. Kimberlin, D.W.; Coen, D.M.; Biron, K.K.; Cohen, J.I.; Lamb, R.A.; McKinlay, M.; Emini, E.A.; Whitley, R.J. Antiviral Res. 1995, 26, 369-401. Good, S.S.; Daluge, S.M.; Ching, S.V.; Ayers, K.M.; Mahony, W.B.; Faletto, M.B.; Domin, B.A.; Owens, B.S.; Dornsife, R.E.; McDowell, J.A.; LaFon, S.W.; Symonds, W.T. Antiviral Res. 1995, 26, A228. Daluge, S.M.; Good, S.S.; Faletto, M.B.; Miller, W.H.; St. Clair, M.H.; Boone, L.R; Tisdale, M.; Parry, N.R.; Reardon, J.E.; Dornsife, R.E.; Averett, D.R.; Krenitsky, T.A. Antimicrob. Agents Chem. 1997 41 1082-1093. Tisdale, M.; Alnadaf, T.; Cousens, D. Antimicrob. Agents Chem. 1997 41 1094-1098. Faletto, M.B.; Miller, W.H.; Garvey, E.P.; St. Clair, M.H.; Daluge, S.M.; Good, S.S. Antimicrob. Agents Chem. 1997 41 1099-1107.
26. 14. Daluge, S.M.; Good, S.S.; Martin, M.T.; Tibbels, S.R.; Miller, W.H.; Averett, D.R.; St. Clair, M.H.; Ayers, K.M. Abstracts of the 34th Interscience Conference on Antimicrobial Agents and Chemotherapy 1994, Abstract #16. Torres, G. GMHC Treatment Issues 1996, 10, 8. Saag, M. Abstracts from The Third Conference on Retroviruses and Opportunistic Infections, abstract 195. Kimberlin, D.W.; Coen, D.M.; Biron, K.K.; Cohen, J.I.; Lamb, R.A.; McKinlay, M.; Emini, E.A.; Whitley, R.J. Antiviral Res. 1995, 26, 369-401. Good, S.S.; Daluge, S.M.; Ching, S.V.; Ayers, K.M.; Mahony, W.B.; Faletto, M.B.; Domin, B.A.; Owens, B.S.; Dornsife, R.E.; McDowell, J.A.; LaFon, S.W.; Symonds, W.T. Antiviral Res. 1995, 26, A228. Daluge, S.M.; Good, S.S.; Faletto, M.B.; Miller, W.H.; St. Clair, M.H.; Boone, L.R; Tisdale, M.; Parry, N.R.; Reardon, J.E.; Dornsife, R.E.; Averett, D.R.; Krenitsky, T.A. Antimicrob. Agents Chem. 1997 41 1082-1093. Tisdale, M.; Alnadaf, T.; Cousens, D. Antimicrob. Agents Chem. 1997 41 1094-1098. Faletto, M.B.; Miller, W.H.; Garvey, E.P.; St. Clair, M.H.; Daluge, S.M.; Good, S.S. Antimicrob. Agents Chem. 1997 41 1099-1107.
27. 15. "Design of Anti-AIDS Drugs" Herdewijn, P.; DeClerq, E.; Elsevier Science: Amsterdam, 1990; pp 141-71.
28. 16. Larder, B.A.; Darby, G.; Richman, D.D. Science 1989, 243, 1731-1734.
29. 17. For a recent comprehensive review on antiviral nucleosides see Mansour, T.S.; Storer, R. Current Pharmaceut. Des. 1997, 3, 227-264
30. 18. Clausen, F.P.; Juhl-Christensen, J. Organic Prep. and Proc. Int. 1993, 25, 373-401.
31. 19. Trost, B.M.; Kuo, G.-H; Benneche, T. J. Am. Chem. Soc. 1988, 110, 621-622.
32. 20. Crimmins, M.T.; King, B.W. J. Org. Chem. 1996, 61, 4192-4193.
33. 21. Mitsunobu, O.; Synthesis 1981, 1. Martin, S.F.; Dodge, J.A. Tetrahedron Lett. 1991, 32, 3017-3020.
34. 21. Mitsunobu, O.; Synthesis 1981, 1. Martin, S.F.; Dodge, J.A. Tetrahedron Lett. 1991, 32, 3017-3020.
35. 22. Wachtmeister, J.; Classon, B.; Samuelsson, B.; Kvarnstrom, D.; Tetrahedron 1995, 51, 2029-2038. Nucleosides and Nucleotides 1995, 14, 405-408.
36. 22. Wachtmeister, J.; Classon, B.; Samuelsson, B.; Kvarnstrom, D.; Tetrahedron 1995, 51, 2029-2038. Nucleosides and Nucleotides 1995, 14, 405-408.
37. 23. Bisacchi, G.S.; Singh, J.; Godfrey, Jr.; J.D.; Kissick, T.P; Mitt, T.; Malley, M.F.; Di Marco, J.D.; Gougoutas, J.Z.; Mueller, R.H.; Zahler, R. J. Org. Chem. 1995, 60, 2902-2905.
38. 24. Jeong, L.S.; Marquez, V.E. Tetrahedron Lett. 1996, 37, 2353-2356.
39. 25. Yoshikawa, M.; Yokokawa, Y.; Inuoe, Y.; Yamaguchi, S.; Murakami, N.; Kitigawa, I. Tetrahedron 1994, 50, 9961-9974.
40. 26. Katagiri, N.; Nomura, M.; Sato, H.; Kaneko, C.; Yusa, K.; Tsuruo, T. J. Med. Chem. 1992, 35, 1882-886.
41. 27. Evans, C.T.; Roberts, S.M.; Shoberu, K.A.; Sutherland, A.G. J. Chem. Soc. Perkin Trans. 1, 1992, 589-592.
42. 28. Wyatt, P.G.; Anslow, A.S.; Coombs, B.A.; Cousins, R.P.C; Evans, D.N.; Gilbert, V.S.; Humber, D.C.; Paternoster, I.L.; Sollis, S.L.; Tapolczay, D.J.; Weingarten, G.G. Nucleosides and Nucleotides 1995, 14, 2039-2049.
43. 29. Shaw, G.; Warrener, R. J. Chem. Soc. 1958, 153. Shaw, G.; Warrener, R. J. Chem. Soc. 1958, 157.
44. 29. Shaw, G.; Warrener, R. J. Chem. Soc. 1958, 153. Shaw, G.; Warrener, R. J. Chem. Soc. 1958, 157.
45. 30. Trost, B.M.; Verhoeven, T.R, "Comprehensive Organometallic Chemistry", Wilkinson, G., ed. Pergamon Press, Oxford, 1982, vol.8, p.799.
46. 31. Trost, B.M.; Li, L.; Guile, S.D. J. Am. Chem. Soc. 1992, 114 , 8745-8747.
47. 32. Katogiri, N.; Ito, Y.; Kitano, K.; Toyota, A.; Kaneko, C. Chem. Pharm. Bull. 1994, 42, 2653-2655.
48. 33. Bajorek, J.J.; Battaglia, R.; Pratt, G.; Sutherland, J.K. J. Chem. Soc. Perkin Trans. I 1974, 1243. Pawson, H.; Maaß, U. Chem. Ber. 1981, 114, 346.
49. 33. Bajorek, J.J.; Battaglia, R.; Pratt, G.; Sutherland, J.K. J. Chem. Soc. Perkin Trans. I 1974, 1243. Pawson, H.; Maaß, U. Chem. Ber. 1981, 114, 346.
50. 34. Evans, C.T.; Roberts, S.M.; Shoberu, K.A.; Sutherland, A.G. J. Chem. Soc. Perkin Trans. 1, 1992, 589-592.
51. 35. Popescu, A.; Hornfeldt, A.-B.; Gronowitz, S.; Johansson, N.G. Nucleosides and Nucleotides 1995, 14, 1233-1249.
52. 36. Saville-Stones, E.A.; Turner, R.M.; Lindell, S.D.; Jennings, N.S.; Head, J.C.; Carver, D.S. Tetrahedron 1994, 50, 6695-6704.
53. 37. MacKeith, R.A.; McCague, R., Olivo, H.F.; Palmer, C.F., Roberts, S.M. J. Chem. Soc. Perkin Trans. 1, 1993, 313-314.
54. 38. Burlina, F.; Favre, A.; Fourrey, J.-L.; Thomas, M. Bioorg. Med. Chem. Lett. 1997, 7, 247-250. Burlina, F.; Clivio, P.; Fourrey, J.-L.; Riche, C.; Thomas, M. Tetrahedron Lett. 1994, 35, 8151-8152.
55. 38. Burlina, F.; Favre, A.; Fourrey, J.-L.; Thomas, M. Bioorg. Med. Chem. Lett. 1997, 7, 247-250. Burlina, F.; Clivio, P.; Fourrey, J.-L.; Riche, C.; Thomas, M. Tetrahedron Lett. 1994, 35, 8151-8152.
56. 39. Aggarwal, V.; Monteiro, N.; Tarver, G.J.; Lindell, S.D. J. Org. Chem. 1996, 61, 1192-1193.
57. 40. Gundersen, L.-L.; Benneche, T.; Undheim, K. Tetrahedron Lett. 1992, 33, 1085-1088.
58. 41 Gundersen, L.-L.; Benneche, T.; Rise, F.; Gogoll, A.; Undheim, K. Acta Chemica Scand. 1992, 46, 761-771.
59. 42. Hildbrand, S. Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236-1240.
60. 43. Hildbrand, S.; Leumann, C.; Scheffold, R. Helv. Chim. Acta 1996, 79, 702-709.
61. 44. Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chemistry Lett. 1994, 1071-1074.
62. 45. Dyatkina, N.; Costisella, B.; Theil, F.; von Janta-Lipinski, M. Tetrahedron Lett. 1994, 35, 1961-1964. Dyatkina, N.; Semizarov, D.; Victorova, L.; Krayevsky, A.; Theil, F.; von Janta-Lipinski, M. Nucleosides and Nucleotides 1995, 14, 723-726. Dyatkina, N.B.; Theil, F.; von Janta-Lipinski, M. Tetrahedron 1995, 51, 761-772.
63. 45. Dyatkina, N.; Costisella, B.; Theil, F.; von Janta-Lipinski, M. Tetrahedron Lett. 1994, 35, 1961-1964. Dyatkina, N.; Semizarov, D.; Victorova, L.; Krayevsky, A.; Theil, F.; von Janta-Lipinski, M. Nucleosides and Nucleotides 1995, 14, 723-726. Dyatkina, N.B.; Theil, F.; von Janta-Lipinski, M. Tetrahedron 1995, 51, 761-772.
64. 45. Dyatkina, N.; Costisella, B.; Theil, F.; von Janta-Lipinski, M. Tetrahedron Lett. 1994, 35, 1961-1964. Dyatkina, N.; Semizarov, D.; Victorova, L.; Krayevsky, A.; Theil, F.; von Janta-Lipinski, M. Nucleosides and Nucleotides 1995, 14, 723-726. Dyatkina, N.B.; Theil, F.; von Janta-Lipinski, M. Tetrahedron 1995, 51, 761-772.
65. 46. Curran, T.; Hay, D.A. Tetrahedron Asymmetry 1996, 7, 2791-2792. Curran, T. Synthetic Commun. 1996, 26, 1209-1221. see also Koga, M.; Schneller, S.W. J. Org. Chem. 1993, 58, 6471-6473.
66. 46. Curran, T.; Hay, D.A. Tetrahedron Asymmetry 1996, 7, 2791-2792. Curran, T. Synthetic Commun. 1996, 26, 1209-1221. see also Koga, M.; Schneller, S.W. J. Org. Chem. 1993, 58, 6471-6473.
67. 46. Curran, T.; Hay, D.A. Tetrahedron Asymmetry 1996, 7, 2791-2792. Curran, T. Synthetic Commun. 1996, 26, 1209-1221. see also Koga, M.; Schneller, S.W. J. Org. Chem. 1993, 58, 6471-6473.
68. 47. Hodgson, D.M.; Witherington, J.; Moloney, B.A. Tetrahedron Asymmetry. 1994, 5, 337-338. Hodgson, D.M.; Witherington, J.; Moloney, B.A. J. Chem. Soc. Perkin Trans. 1 1994, 3373-3378.
69. 47. Hodgson, D.M.; Witherington, J.; Moloney, B.A. Tetrahedron Asymmetry. 1994, 5, 337-338. Hodgson, D.M.; Witherington, J.; Moloney, B.A. J. Chem. Soc. Perkin Trans. 1 1994, 3373-3378.
70. 48. Ritter, A.R.; Miller, M.J. J. Org. Chem. 1994, 59, 4602-4611
71. 49. Zhang, D.; Ghosh, A.; Suling, C.; Miller, M.J. Tetrahedron Lett. 1996, 37, 3799-3802.
72. 50. Ghosh, A.; Ritter, A.R; Miller, M.J. J. Org. Chem. 1995, 60, 5808-5813.
73. 51. Ghosh, A.; Miller, M.J. Tetrahedron Lett. 1995, 36, 6399-6402.
74. 52. Hansel, J.-G., O'Hogan, S.; Lensky, S.; Ritter, A.R.; Miller, M.J. Tetrahedron Lett. 1995, 36, 2913-2916.
75. 53. Berrenger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523-5526.
76. 54. Trost, B.M.; Madsen, R.; Guile, S.G.; Elia, A.E.H. Angew. Chem. Int. Ed. Engl. 1996, 35, 1569-1572.
77. 55. Trost, B.M.; Madsen, R.; Guile, S.G. Tetrahedron Lett. 1997, 58, 1707-1710.
78. 56. Jung, M.E.; Rhee, H. J. Org. Chem. 1994, 59, 4719-4720.
79. 57. Katagiri, N.; Makino, M.; Tamura, T.; Kaneko, C. Chem. Pharm. Bull. 1996, 44, 850-852.
80. 58. Katagiri, N.; Takebayashi, M.; Kokufuda, H.; Kaneko, C.; Kanehira, K.; Torihara, M. J. Org. Chem. 1997, 62, 1580-1581.
81. 59. For example see: Vince, R.; Hua, M.; Brownell, J.; Daluge, S.M.; Lee, F.C.; Shannon, W.M.; Lavelle, G.C.; Qualls, J.; Weislow, O.S.; Kiser, R.; Canonico, P.G.; Schultz, R.H.; Narayanan, V.L.; Mayo, J.G.; Shoemaker, R.H.; Boyd, M.R. Biochem. Biophys. Res. Commun. 1988, 156, 1046-1053. "Therapeutic Nucleosides" Daluge, S.M. U.S. Patent 1991, patent number 5,034,394, Daluge, S.M.; Good, S.S.; Faletto, M.B.; Miller, W.H.; St. Clair, M.H.; Boone, L.R; Tisdale, M.; Parry, N.R.; Reardon, J.E.; Dornsife, R.E.; Averett, D.R.; Krenitsky, T.A. Antimicrob. Agents Chem. 1997, 41, 1082-1093.
82. 59. For example see: Vince, R.; Hua, M.; Brownell, J.; Daluge, S.M.; Lee, F.C.; Shannon, W.M.; Lavelle, G.C.; Qualls, J.; Weislow, O.S.; Kiser, R.; Canonico, P.G.; Schultz, R.H.; Narayanan, V.L.; Mayo, J.G.; Shoemaker, R.H.; Boyd, M.R. Biochem. Biophys. Res. Commun. 1988, 156, 1046-1053. "Therapeutic Nucleosides" Daluge, S.M. U.S. Patent 1991, patent number 5,034,394, Daluge, S.M.; Good, S.S.; Faletto, M.B.; Miller, W.H.; St. Clair, M.H.; Boone, L.R; Tisdale, M.; Parry, N.R.; Reardon, J.E.; Dornsife, R.E.; Averett, D.R.; Krenitsky, T.A. Antimicrob. Agents Chem. 1997, 41, 1082-1093.
83. 59. For example see: Vince, R.; Hua, M.; Brownell, J.; Daluge, S.M.; Lee, F.C.; Shannon, W.M.; Lavelle, G.C.; Qualls, J.; Weislow, O.S.; Kiser, R.; Canonico, P.G.; Schultz, R.H.; Narayanan, V.L.; Mayo, J.G.; Shoemaker, R.H.; Boyd, M.R. Biochem. Biophys. Res. Commun. 1988, 156, 1046-1053. "Therapeutic Nucleosides" Daluge, S.M. U.S. Patent 1991, patent number 5,034,394, Daluge, S.M.; Good, S.S.; Faletto, M.B.; Miller, W.H.; St. Clair, M.H.; Boone, L.R; Tisdale, M.; Parry, N.R.; Reardon, J.E.; Dornsife, R.E.; Averett, D.R.; Krenitsky, T.A. Antimicrob. Agents Chem. 1997, 41, 1082-1093.
84. 60. Taylor, S.J.C.; McCague, R.; Wisdom, R.; Lee, C.; Dickson, K.; Ruecroft, G.; O'Brien, F.; Littlechild, J.; Bevan, J.; Roberts, S.M.; Evans, C.T. Tetrhedron Asymmetry 1993, 4, 1117-1128. Bicyclic lactam 134 is commercially available from Chiroscience, Inc.
85. 61. Palmer, C.F.; McCague, J. J. Chem.Soc. Perkin Trans I 1995, 1201-1203.
86. 62. Csuk, R.; Dorr, P. Tetrahedron Asymmetry 1994, 5, 269-276.
87. 63. Csuk, R.; Dorr, P. Tetrahedron 1995, 51, 5789-5798.
88. 64. Bray, B.L.; Dolan, S.C.; Halter, B.; Lackey, J.W.; Schilling, M.B.; Tapolczay, D.J. Tetrahedron Lett. 1995, 36, 4483-4486.
89. 65. Wyatt, P.G.; Anslow, A.S.; Coombs, B.A.; Cousins, R.P.C.; Evans, D.N.; Gilbert, V.S.; Humber, D.C.; Paternoster, I.L.; Sollis, S.L.; Tapolczay, D.J.; Weingarten, G.G. Nucleosides and Nucleotides, 1995, 14, 2039-2049.
90. 66. Katagiri, N.; Matsuhashi, Y.; Kokufuda, H.; Takebayashi, M.; Kaneko, C. Tetrahedron Lett. 1997, 35, 1961-1964.
91. 67. Katagiri, N.; Nomura, M.; Sato, H.; Kaneko, C.; Yusa, K.; Tsuruo, T. J. Med. Chem. 1992, 35, 1882-1886.
92. 68. Handa, S.; Earlam, G.J.; Geary, P.J.; Hawes, J.E.; Phillips, G.T.; Pryce, R.J.; Ryback, G.; Shears, J.H. J. Chem. Soc. Perkin Trans I 1994, 1885-1886.
93. 69. Mohar, B.; Stimac, A.; Kobe, J. Tetrahedron Asymmetry 1994, 5, 863-868.
94. 70. Mohar, B.; Stimac, A.; Kobe, J. Nucleosides and Nucleotides 1993, 12, 793-802.
95. 71. Arita, M.; Adachi, K.; Ito, Y. Sawa, H.; Ohno, M. J. Am. Chem. Soc. 1983, 103, 4049-4055.
96. 72. Tanaka, M.; Norimine, Y.; Fujita, T.; Suemune, H.; Sakai, K. J. Org. Chem. 1996, 61, 6952-6957.
97. 73. Tanaka, M.; Yoshioka, M.; Sakai, K. Tetrahedron: Asymmetry 1993, 4, 981-996.
98. 74. Diaz, M.; Ibarzo, J.; Jimenez, J.M.; Ortuno, R.M.; Tetrahedron: Asymmetry. 1994, 5, 129-140.
99. 75. Casas, R.; Chen, Z.; Diaz, M.; Hanafi, N.; Ibarzo, J.; Jimenez, J.M.; Ortuno, R.M. Anales de Quimica 1995, 91, 42-49.
100. 76. Boyer, S.J.; Leahy, J.W. J. Org. Chem. 1997, 62, 3976-3980.
101. 77. Trost, B.M.; Stenkamp, D.; Pulley, S.R. Chem. Eur. J. 1995, 1, 568-572.
102. 78. Deardorff, D.R.; Savin, K.A.; Justman, C.J.; Karanjawala, Z.E.; Sheppeck, II, J.E.; Hager, D.C.; Aydin, N. J. Org. Chem. 1996, 61, 3616-3622.
103. 79. Borthwick, A.D.; Crame, A.J.; Exall, A.M.; Weingarten, G.G. Tetrahedron Lett. 1994, 35, 7677-7680.
104. 80. Lang, H.; Moser, H.E. Helv. Chim. Acta 1994, 77, 1527-1540.
105. 81. Zhang, D.; Ghosh, A.; Suling, C.; Miller, M.J. Tetrahedron Lett. 1996, 37, 3799-3802.
106. 82. Yoshikawa, M.; Yokokawa, Y.; Inuoe, Y.; Yamaguchi, S.; Murakami, N. Tetrahedron 1994, 50, 9961 -9974.
107. 83. Ohira, S.; Sawamoto, T.; Yamata, M.; Tetrahedron Lett. 1995, 36, 1537-1538.
108. 84. Wang, P.; Agrofoglio, L.A.; Newton, M.G.; Chu, C.K. Tetrahedron Lett. 1997, 38, 4207-4210.
109. 85. Ali, S.M.; Ramesh, K.; Borchardt, R.T. Tetrahedron Lett. 1990, 31, 1509-1512.
110. 86. Marquez, V.E.; Lim. M.-I.; Tseng, C. K.-H.; Markovac, A.; Priest, M.A.; Khan, M.S.; Kaskar, B. J. Org. Chem. 1988, 53, 5709-5714.
111. 87. Altmann, K.-H.; Kesselring, R.; Francotte, E.; Rihs, G. Tetrahedron Lett. 1994, 35, 2331-2334.
112. 88. Marquez V.E.; Siddiqui, M.A.; Ezzitouni, A.; Russ, P.; Wang, J.; Wagner, R.W.; Matteucci, M.D. J. Med. Chem. 1996 39, 3739-3747.
113. 89. Marquez, V.E.; Lim, M.-I.; Tseng, C.K.-H.; Markovac, A.; Priest, M.A.; Khan, M.S.; Kaskar, B. J. Org. Chem. 1988, 53, 5709-5714.
114. 90. Park, K.H.; Rapoport, H. J. Org. Chem. 1994, 59, 394-399.
115. 91. Campbell, J.A.; Lee, W.K.; Rapoport, H. J. Org. Chem. 1995, 60, 4602-4616.
116. 92. Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649-1652.
117. 93. Martinez, L.S.; Nugent, W.A.; Jacobsen, E.N. J. Org. Chem. 1996, 61, 7963-7966.
118. 94. Rosenquist, A.; Kvarnstrom, I.; Svensson, C.T.; Classon, B.; Samuelsson, B; Acta Chem. Scand. 1992, 46, 1127-1129.
119. 95. Rosenquist, A.; Kvarnstrom, I.; Svensson, C.T.; Classon, B.; Samuelsson, B; J. Org. Chem. 1994, 59, 1779-1782.
120. 96. Janson, M.; Svansson, L.; Svensson, S.C.T.; Kvarnstrom, D.; Classon, B.; Samuelsson, B. Nucleosides and Nucleotides 1992, 11, 1739-1747.
121. 97. Wachtmeister, J.; Classon, B.; Samuelsson, B.; Kvarnstrom, D. Tetrahedron 1995, 51, 2029-2038. Nucleosides and Nucleotides 1995, 14, 405-408.
122. 97. Wachtmeister, J.; Classon, B.; Samuelsson, B.; Kvarnstrom, D. Tetrahedron 1995, 51, 2029-2038. Nucleosides and Nucleotides 1995, 14, 405-408.