An efficient asymmetric approach to carbocyclic nucleosides: Asymmetric synthesis of 1592U89, a potent inhibitor of HIV reverse transcriptase

Journal of Organic Chemistry

Volumn 61, Issue 13, 1996, Pages 4192-4193

  Crimmins, Michael T ^a   King, Bryan W ^a  

^a UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABACAVIR; ANTIVIRUS AGENT; CARBOCYCLIC NUCLEOSIDE; CARBOVIR; RNA DIRECTED DNA POLYMERASE INHIBITOR;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030018804     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960708p     Document Type: Article

References (37)

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8. For some recent carbovir syntheses, see: (a) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523-5526. (b) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236-1240. (c) Legraverend, M.; Aubertin, A. M.; Obert, G.; Huel, C.; Bisagni, E. Nucleosides Nucleotides 1994, 13, 915-923. (d) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129-140. (e) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719-4720. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071-1074. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649-1652. (h) MacKeith, R. A.; McCague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313-314. (i) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 4449-4452. (j) Evans, C. T.; Robert, S. M.; Shoberu, K. A.; Sutherland, A. G., J. Chem. Soc., Perkin Trans. 1 1992, 589-592. (k) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745-8747. (l) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990-4993. (m) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373-3378.
9. For some recent carbovir syntheses, see: (a) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523-5526. (b) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236-1240. (c) Legraverend, M.; Aubertin, A. M.; Obert, G.; Huel, C.; Bisagni, E. Nucleosides Nucleotides 1994, 13, 915-923. (d) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129-140. (e) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719-4720. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071-1074. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649-1652. (h) MacKeith, R. A.; McCague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313-314. (i) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 4449-4452. (j) Evans, C. T.; Robert, S. M.; Shoberu, K. A.; Sutherland, A. G., J. Chem. Soc., Perkin Trans. 1 1992, 589-592. (k) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745-8747. (l) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990-4993. (m) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373-3378.
10. For some recent carbovir syntheses, see: (a) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523-5526. (b) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236-1240. (c) Legraverend, M.; Aubertin, A. M.; Obert, G.; Huel, C.; Bisagni, E. Nucleosides Nucleotides 1994, 13, 915-923. (d) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129-140. (e) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719-4720. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071-1074. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649-1652. (h) MacKeith, R. A.; McCague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313-314. (i) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 4449-4452. (j) Evans, C. T.; Robert, S. M.; Shoberu, K. A.; Sutherland, A. G., J. Chem. Soc., Perkin Trans. 1 1992, 589-592. (k) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745-8747. (l) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990-4993. (m) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373-3378.
11. For some recent carbovir syntheses, see: (a) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523-5526. (b) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236-1240. (c) Legraverend, M.; Aubertin, A. M.; Obert, G.; Huel, C.; Bisagni, E. Nucleosides Nucleotides 1994, 13, 915-923. (d) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129-140. (e) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719-4720. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071-1074. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649-1652. (h) MacKeith, R. A.; McCague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313-314. (i) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 4449-4452. (j) Evans, C. T.; Robert, S. M.; Shoberu, K. A.; Sutherland, A. G., J. Chem. Soc., Perkin Trans. 1 1992, 589-592. (k) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745-8747. (l) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990-4993. (m) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373-3378.
12. For some recent carbovir syntheses, see: (a) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523-5526. (b) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236-1240. (c) Legraverend, M.; Aubertin, A. M.; Obert, G.; Huel, C.; Bisagni, E. Nucleosides Nucleotides 1994, 13, 915-923. (d) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129-140. (e) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719-4720. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071-1074. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649-1652. (h) MacKeith, R. A.; McCague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313-314. (i) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 4449-4452. (j) Evans, C. T.; Robert, S. M.; Shoberu, K. A.; Sutherland, A. G., J. Chem. Soc., Perkin Trans. 1 1992, 589-592. (k) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745-8747. (l) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990-4993. (m) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373-3378.
13. For some recent carbovir syntheses, see: (a) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523-5526. (b) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236-1240. (c) Legraverend, M.; Aubertin, A. M.; Obert, G.; Huel, C.; Bisagni, E. Nucleosides Nucleotides 1994, 13, 915-923. (d) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129-140. (e) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719-4720. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071-1074. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649-1652. (h) MacKeith, R. A.; McCague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313-314. (i) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 4449-4452. (j) Evans, C. T.; Robert, S. M.; Shoberu, K. A.; Sutherland, A. G., J. Chem. Soc., Perkin Trans. 1 1992, 589-592. (k) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745-8747. (l) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990-4993. (m) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373-3378.
14. For some recent carbovir syntheses, see: (a) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523-5526. (b) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236-1240. (c) Legraverend, M.; Aubertin, A. M.; Obert, G.; Huel, C.; Bisagni, E. Nucleosides Nucleotides 1994, 13, 915-923. (d) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129-140. (e) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719-4720. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071-1074. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649-1652. (h) MacKeith, R. A.; McCague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313-314. (i) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 4449-4452. (j) Evans, C. T.; Robert, S. M.; Shoberu, K. A.; Sutherland, A. G., J. Chem. Soc., Perkin Trans. 1 1992, 589-592. (k) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745-8747. (l) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990-4993. (m) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373-3378.
15. For some recent carbovir syntheses, see: (a) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523-5526. (b) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236-1240. (c) Legraverend, M.; Aubertin, A. M.; Obert, G.; Huel, C.; Bisagni, E. Nucleosides Nucleotides 1994, 13, 915-923. (d) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129-140. (e) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719-4720. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071-1074. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649-1652. (h) MacKeith, R. A.; McCague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313-314. (i) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 4449-4452. (j) Evans, C. T.; Robert, S. M.; Shoberu, K. A.; Sutherland, A. G., J. Chem. Soc., Perkin Trans. 1 1992, 589-592. (k) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745-8747. (l) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990-4993. (m) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373-3378.
16. For some recent carbovir syntheses, see: (a) Berranger, T.; Langlois, Y. Tetrahedron Lett. 1995, 36, 5523-5526. (b) Hildebrand, S.; Troxler, T.; Scheffold, R. Helv. Chim. Acta 1994, 77, 1236-1240. (c) Legraverend, M.; Aubertin, A. M.; Obert, G.; Huel, C.; Bisagni, E. Nucleosides Nucleotides 1994, 13, 915-923. (d) Diaz, M.; Ibarzo, J.; Jimenez, J. M.; Ortuno, R. M. Tetrahedron: Asymmetry 1994, 5, 129-140. (e) Jung, M. E.; Rhee, H. J. Org. Chem. 1994, 59, 4719-4720. (f) Nokami, J.; Matsuura, H.; Nakasima, K.; Shibata, S. Chem. Lett. 1994, 1071-1074. (g) Asami, M.; Takahashi, J.; Inoue, S. Tetrahedron: Asymmetry 1994, 5, 1649-1652. (h) MacKeith, R. A.; McCague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313-314. (i) Jung, M. E.; Rhee, H. Tetrahedron Lett. 1993, 34, 4449-4452. (j) Evans, C. T.; Robert, S. M.; Shoberu, K. A.; Sutherland, A. G., J. Chem. Soc., Perkin Trans. 1 1992, 589-592. (k) Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745-8747. (l) Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990-4993. (m) Hodgson, D. M.; Witherington, J.; Moloney, B. A. J. Chem. Soc., Perkin Trans. 1 1994, 3373-3378.
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