Synthesis of a novel trisubstituted cyclobutane nucleoside analogue. Unexpected C4-C3 ring contractions in related reactions

Tetrahedron

Volumn 53, Issue 16, 1997, Pages 5797-5812

  Mévellec, Laurence ^a   Huet, François ^a  

^a UNIVERSITÉ DU MAINE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANE DERIVATIVE; NUCLEOSIDE ANALOG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG SCREENING; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0342940776     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00266-4     Document Type: Article

References (28)

1. Recent reviews: Huryn, D.M.; Okabe, M. Chem. Rev. 1992, 92, 1745; Borthwick, A.D.; Biggadike, K. Tetrahedron 1992, 48, 571; Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S.R.; Earl, R.A.; Guedj, R. Ibid. 1994, 50, 10611.
2. Recent reviews: Huryn, D.M.; Okabe, M. Chem. Rev. 1992, 92, 1745; Borthwick, A.D.; Biggadike, K. Tetrahedron 1992, 48, 571; Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S.R.; Earl, R.A.; Guedj, R. Ibid. 1994, 50, 10611.
3. Recent reviews: Huryn, D.M.; Okabe, M. Chem. Rev. 1992, 92, 1745; Borthwick, A.D.; Biggadike, K. Tetrahedron 1992, 48, 571; Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S.R.; Earl, R.A.; Guedj, R. Ibid. 1994, 50, 10611.
4. For several papers on dihydroxylated cyclobutane nucleosides see for instance the following ones and references therein: Jacobs, G.A.; Tino, J.A.; Zahler, R. Tetrahedron Lett. 1989, 30, 6955; Honjo, M.; Maruyama, T.; Sato, Y.; Horii, T. Chem. Pharm. Bull. 1989, 37, 1413; Katagiri, N.; Sato, H.; Kaneko, C. Ibid. 1990, 38, 288; Maruyama, T.; Sato, Y.; Horii, T.; Shiota, H.; Nitta, K.; Shirasaka, T.; Mitsuya, H.; Honjo, M. Ibid 1990, 38, 2719; Boumchita, H.; Legraverend, M.; Huel, C.; Bisagni, E. J. Heterocycl. Chem. 1990, 27, 1815; Boumchita, H.; Legraverend, M.; Guilhem, J.; Bisagni, E. Heterocycles 1991, 32, 867; Jung, M.E.; Sledeski, A.W. J. Chem. Soc., Chem. Commun. 1993, 589; Lin, T.-S.; Luo, M.-Z.; Liu, M.-C. Nucleosides & Nucleotides 1994, 13, 245; 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.
5. For several papers on dihydroxylated cyclobutane nucleosides see for instance the following ones and references therein: Jacobs, G.A.; Tino, J.A.; Zahler, R. Tetrahedron Lett. 1989, 30, 6955; Honjo, M.; Maruyama, T.; Sato, Y.; Horii, T. Chem. Pharm. Bull. 1989, 37, 1413; Katagiri, N.; Sato, H.; Kaneko, C. Ibid. 1990, 38, 288; Maruyama, T.; Sato, Y.; Horii, T.; Shiota, H.; Nitta, K.; Shirasaka, T.; Mitsuya, H.; Honjo, M. Ibid 1990, 38, 2719; Boumchita, H.; Legraverend, M.; Huel, C.; Bisagni, E. J. Heterocycl. Chem. 1990, 27, 1815; Boumchita, H.; Legraverend, M.; Guilhem, J.; Bisagni, E. Heterocycles 1991, 32, 867; Jung, M.E.; Sledeski, A.W. J. Chem. Soc., Chem. Commun. 1993, 589; Lin, T.-S.; Luo, M.-Z.; Liu, M.-C. Nucleosides & Nucleotides 1994, 13, 245; 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.
6. For several papers on dihydroxylated cyclobutane nucleosides see for instance the following ones and references therein: Jacobs, G.A.; Tino, J.A.; Zahler, R. Tetrahedron Lett. 1989, 30, 6955; Honjo, M.; Maruyama, T.; Sato, Y.; Horii, T. Chem. Pharm. Bull. 1989, 37, 1413; Katagiri, N.; Sato, H.; Kaneko, C. Ibid. 1990, 38, 288; Maruyama, T.; Sato, Y.; Horii, T.; Shiota, H.; Nitta, K.; Shirasaka, T.; Mitsuya, H.; Honjo, M. Ibid 1990, 38, 2719; Boumchita, H.; Legraverend, M.; Huel, C.; Bisagni, E. J. Heterocycl. Chem. 1990, 27, 1815; Boumchita, H.; Legraverend, M.; Guilhem, J.; Bisagni, E. Heterocycles 1991, 32, 867; Jung, M.E.; Sledeski, A.W. J. Chem. Soc., Chem. Commun. 1993, 589; Lin, T.-S.; Luo, M.-Z.; Liu, M.-C. Nucleosides & Nucleotides 1994, 13, 245; 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.
7. For several papers on dihydroxylated cyclobutane nucleosides see for instance the following ones and references therein: Jacobs, G.A.; Tino, J.A.; Zahler, R. Tetrahedron Lett. 1989, 30, 6955; Honjo, M.; Maruyama, T.; Sato, Y.; Horii, T. Chem. Pharm. Bull. 1989, 37, 1413; Katagiri, N.; Sato, H.; Kaneko, C. Ibid. 1990, 38, 288; Maruyama, T.; Sato, Y.; Horii, T.; Shiota, H.; Nitta, K.; Shirasaka, T.; Mitsuya, H.; Honjo, M. Ibid 1990, 38, 2719; Boumchita, H.; Legraverend, M.; Huel, C.; Bisagni, E. J. Heterocycl. Chem. 1990, 27, 1815; Boumchita, H.; Legraverend, M.; Guilhem, J.; Bisagni, E. Heterocycles 1991, 32, 867; Jung, M.E.; Sledeski, A.W. J. Chem. Soc., Chem. Commun. 1993, 589; Lin, T.-S.; Luo, M.-Z.; Liu, M.-C. Nucleosides & Nucleotides 1994, 13, 245; 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.
8. For several papers on dihydroxylated cyclobutane nucleosides see for instance the following ones and references therein: Jacobs, G.A.; Tino, J.A.; Zahler, R. Tetrahedron Lett. 1989, 30, 6955; Honjo, M.; Maruyama, T.; Sato, Y.; Horii, T. Chem. Pharm. Bull. 1989, 37, 1413; Katagiri, N.; Sato, H.; Kaneko, C. Ibid. 1990, 38, 288; Maruyama, T.; Sato, Y.; Horii, T.; Shiota, H.; Nitta, K.; Shirasaka, T.; Mitsuya, H.; Honjo, M. Ibid 1990, 38, 2719; Boumchita, H.; Legraverend, M.; Huel, C.; Bisagni, E. J. Heterocycl. Chem. 1990, 27, 1815; Boumchita, H.; Legraverend, M.; Guilhem, J.; Bisagni, E. Heterocycles 1991, 32, 867; Jung, M.E.; Sledeski, A.W. J. Chem. Soc., Chem. Commun. 1993, 589; Lin, T.-S.; Luo, M.-Z.; Liu, M.-C. Nucleosides & Nucleotides 1994, 13, 245; 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.
9. For several papers on dihydroxylated cyclobutane nucleosides see for instance the following ones and references therein: Jacobs, G.A.; Tino, J.A.; Zahler, R. Tetrahedron Lett. 1989, 30, 6955; Honjo, M.; Maruyama, T.; Sato, Y.; Horii, T. Chem. Pharm. Bull. 1989, 37, 1413; Katagiri, N.; Sato, H.; Kaneko, C. Ibid. 1990, 38, 288; Maruyama, T.; Sato, Y.; Horii, T.; Shiota, H.; Nitta, K.; Shirasaka, T.; Mitsuya, H.; Honjo, M. Ibid 1990, 38, 2719; Boumchita, H.; Legraverend, M.; Huel, C.; Bisagni, E. J. Heterocycl. Chem. 1990, 27, 1815; Boumchita, H.; Legraverend, M.; Guilhem, J.; Bisagni, E. Heterocycles 1991, 32, 867; Jung, M.E.; Sledeski, A.W. J. Chem. Soc., Chem. Commun. 1993, 589; Lin, T.-S.; Luo, M.-Z.; Liu, M.-C. Nucleosides & Nucleotides 1994, 13, 245; 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.
10. For several papers on dihydroxylated cyclobutane nucleosides see for instance the following ones and references therein: Jacobs, G.A.; Tino, J.A.; Zahler, R. Tetrahedron Lett. 1989, 30, 6955; Honjo, M.; Maruyama, T.; Sato, Y.; Horii, T. Chem. Pharm. Bull. 1989, 37, 1413; Katagiri, N.; Sato, H.; Kaneko, C. Ibid. 1990, 38, 288; Maruyama, T.; Sato, Y.; Horii, T.; Shiota, H.; Nitta, K.; Shirasaka, T.; Mitsuya, H.; Honjo, M. Ibid 1990, 38, 2719; Boumchita, H.; Legraverend, M.; Huel, C.; Bisagni, E. J. Heterocycl. Chem. 1990, 27, 1815; Boumchita, H.; Legraverend, M.; Guilhem, J.; Bisagni, E. Heterocycles 1991, 32, 867; Jung, M.E.; Sledeski, A.W. J. Chem. Soc., Chem. Commun. 1993, 589; Lin, T.-S.; Luo, M.-Z.; Liu, M.-C. Nucleosides & Nucleotides 1994, 13, 245; 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.
11. For several papers on dihydroxylated cyclobutane nucleosides see for instance the following ones and references therein: Jacobs, G.A.; Tino, J.A.; Zahler, R. Tetrahedron Lett. 1989, 30, 6955; Honjo, M.; Maruyama, T.; Sato, Y.; Horii, T. Chem. Pharm. Bull. 1989, 37, 1413; Katagiri, N.; Sato, H.; Kaneko, C. Ibid. 1990, 38, 288; Maruyama, T.; Sato, Y.; Horii, T.; Shiota, H.; Nitta, K.; Shirasaka, T.; Mitsuya, H.; Honjo, M. Ibid 1990, 38, 2719; Boumchita, H.; Legraverend, M.; Huel, C.; Bisagni, E. J. Heterocycl. Chem. 1990, 27, 1815; Boumchita, H.; Legraverend, M.; Guilhem, J.; Bisagni, E. Heterocycles 1991, 32, 867; Jung, M.E.; Sledeski, A.W. J. Chem. Soc., Chem. Commun. 1993, 589; Lin, T.-S.; Luo, M.-Z.; Liu, M.-C. Nucleosides & Nucleotides 1994, 13, 245; 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.
12. For several papers on dihydroxylated cyclobutane nucleosides see for instance the following ones and references therein: Jacobs, G.A.; Tino, J.A.; Zahler, R. Tetrahedron Lett. 1989, 30, 6955; Honjo, M.; Maruyama, T.; Sato, Y.; Horii, T. Chem. Pharm. Bull. 1989, 37, 1413; Katagiri, N.; Sato, H.; Kaneko, C. Ibid. 1990, 38, 288; Maruyama, T.; Sato, Y.; Horii, T.; Shiota, H.; Nitta, K.; Shirasaka, T.; Mitsuya, H.; Honjo, M. Ibid 1990, 38, 2719; Boumchita, H.; Legraverend, M.; Huel, C.; Bisagni, E. J. Heterocycl. Chem. 1990, 27, 1815; Boumchita, H.; Legraverend, M.; Guilhem, J.; Bisagni, E. Heterocycles 1991, 32, 867; Jung, M.E.; Sledeski, A.W. J. Chem. Soc., Chem. Commun. 1993, 589; Lin, T.-S.; Luo, M.-Z.; Liu, M.-C. Nucleosides & Nucleotides 1994, 13, 245; 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.
13. Shimada, N.; Hasegawa, S.; Harada, T.; Tomisawa, T.; Fujii, A.; Takita, T. J. Antibiotics 1986, 39, 1623; Hoshino, H.; Shimitzu, N.; Shimada, N.; Takita, T.; Takeuchi, T. Ibid. 1987, 40, 1077.
14. Shimada, N.; Hasegawa, S.; Harada, T.; Tomisawa, T.; Fujii, A.; Takita, T. J. Antibiotics 1986, 39, 1623; Hoshino, H.; Shimitzu, N.; Shimada, N.; Takita, T.; Takeuchi, T. Ibid. 1987, 40, 1077.
15. Mévellec, L.; Huet, F. Tetrahedron 1994, 50, 13145.
16. Mévellec, L.; Evers, M.; Huet, F. Tetrahedron 1996, 52, 15103.
17. Murphy, D.K.; Alumbaugh, R.L.; Rickborn, B. J. Am. Chem. Soc. 1969, 91, 2649; Gurudutt, K.N.; Ravindranath, B. Synthesis 1983, 888.
18. Murphy, D.K.; Alumbaugh, R.L.; Rickborn, B. J. Am. Chem. Soc. 1969, 91, 2649; Gurudutt, K.N.; Ravindranath, B. Synthesis 1983, 888.
19. We thank Professor S.M. Roberts and Doctor Y.-I. Ichikawa for sending of useful experimental details on these kind of reactions.
20. Hanessian, S.; Liak, T.J.; Vanasse, B. Synthesis 1981, 396.
21. Mancuso, A.J.; Swern, D. Synthesis 1981, 165.
22. Vidal, J.; Huet, F. J. Org. Chem. 1988, 53, 611.
23. Mitsunobu, O. Synthesis 1981, 1.
24. For reviews on this topic see: Conia, J.M.; Salaün, J. Acc. Chem. Res. 1972, 5, 33; Conia, J.M.; Robson, M.J. Angew. Chem. Internat. Edit. 1975, 14, 473; Salaün, J. in Rappoport, Z. The Chemistry of the Cyclopropyl Group ch 13, 809, J. Wiley and sons, 1987; For recent papers see : Mévellec, L.; Huet, F. Tetrahedron Lett. 1995, 36, 7441; Estieu, K.; Ollivier, J.; Salaün, J. Ibid. 1996, 37, 623.
25. For reviews on this topic see: Conia, J.M.; Salaün, J. Acc. Chem. Res. 1972, 5, 33; Conia, J.M.; Robson, M.J. Angew. Chem. Internat. Edit. 1975, 14, 473; Salaün, J. in Rappoport, Z. The Chemistry of the Cyclopropyl Group ch 13, 809, J. Wiley and sons, 1987; For recent papers see : Mévellec, L.; Huet, F. Tetrahedron Lett. 1995, 36, 7441; Estieu, K.; Ollivier, J.; Salaün, J. Ibid. 1996, 37, 623.
26. For reviews on this topic see: Conia, J.M.; Salaün, J. Acc. Chem. Res. 1972, 5, 33; Conia, J.M.; Robson, M.J. Angew. Chem. Internat. Edit. 1975, 14, 473; Salaün, J. in Rappoport, Z. The Chemistry of the Cyclopropyl Group ch 13, 809, J. Wiley and sons, 1987; For recent papers see : Mévellec, L.; Huet, F. Tetrahedron Lett. 1995, 36, 7441; Estieu, K.; Ollivier, J.; Salaün, J. Ibid. 1996, 37, 623.
27. For reviews on this topic see: Conia, J.M.; Salaün, J. Acc. Chem. Res. 1972, 5, 33; Conia, J.M.; Robson, M.J. Angew. Chem. Internat. Edit. 1975, 14, 473; Salaün, J. in Rappoport, Z. The Chemistry of the Cyclopropyl Group ch 13, 809, J. Wiley and sons, 1987; For recent papers see : Mévellec, L.; Huet, F. Tetrahedron Lett. 1995, 36, 7441; Estieu, K.; Ollivier, J.; Salaün, J. Ibid. 1996, 37, 623.
28. For reviews on this topic see: Conia, J.M.; Salaün, J. Acc. Chem. Res. 1972, 5, 33; Conia, J.M.; Robson, M.J. Angew. Chem. Internat. Edit. 1975, 14, 473; Salaün, J. in Rappoport, Z. The Chemistry of the Cyclopropyl Group ch 13, 809, J. Wiley and sons, 1987; For recent papers see : Mévellec, L.; Huet, F. Tetrahedron Lett. 1995, 36, 7441; Estieu, K.; Ollivier, J.; Salaün, J. Ibid. 1996, 37, 623.