New synthetic route to 2-pyridones and its application toward the synthesis of (±)-ipalbidine

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 438-439

  Sheehan, Scott M ^a   Padwa, Albert ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRIDONE DERIVATIVE; ALKALOID; IPALBIDINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS;

EID: 0031038105     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961690l     Document Type: Article

References (33)

1. Rubiralta, M.; Giralt, E.; Diez, A. Piperidine: Structure, Preparation, Reactivity, and Synthetic Applications of Piperidine and its Derivatives; Elsevier: Amsterdam, 1991.
2. Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; J. Wiley and Sons: New York. The Alkaloids, Specialist Periodical Reports; The Royal Society of Chemistry: London. The Alkaloids; Brossi, A. Ed.; Academic Press: New York. Natural Products Report; The Royal Society of Chemistry: London.
3. Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; J. Wiley and Sons: New York. The Alkaloids, Specialist Periodical Reports; The Royal Society of Chemistry: London. The Alkaloids; Brossi, A. Ed.; Academic Press: New York. Natural Products Report; The Royal Society of Chemistry: London.
4. Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; J. Wiley and Sons: New York. The Alkaloids, Specialist Periodical Reports; The Royal Society of Chemistry: London. The Alkaloids; Brossi, A. Ed.; Academic Press: New York. Natural Products Report; The Royal Society of Chemistry: London.
5. Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; J. Wiley and Sons: New York. The Alkaloids, Specialist Periodical Reports; The Royal Society of Chemistry: London. The Alkaloids; Brossi, A. Ed.; Academic Press: New York. Natural Products Report; The Royal Society of Chemistry: London.
6. Molenda, J. J.; Jones, M. M.; Johnston, D. S.; Walker, E. M.; Cannon, D. J. Med. Chem. 1994, 37, 4363.
7. Elbein, A. D.; Molyneux, R. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1981; Vol. 5, pp 1-54.
8. Meislich, H. Chemistry of Heterocyclic Compounds; Interscience Publishers: New York, 1962; Chapter 12, p 509. Tieckelmann, H. Chemistry of Heterocyclic Compounds; Interscience Publishers: New York, 1974; Chapter 12, p 597.
9. Meislich, H. Chemistry of Heterocyclic Compounds; Interscience Publishers: New York, 1962; Chapter 12, p 509. Tieckelmann, H. Chemistry of Heterocyclic Compounds; Interscience Publishers: New York, 1974; Chapter 12, p 597.
10. Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123. Padwa, A.; Marino, J. P., Jr.; Osterhout, M. H. J. Org. Chem. 1995, 60, 2704. Padwa, A.; Hertzog, D. L; Nadler, W. R. J. Org. Chem. 1994, 59, 7072. Marino, J. P., Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A.; Padwa, A. J. Org. Chem. 1994, 59, 5518. Padwa, A.; Hertzog, D. L.; Nadler, W. R.; Osterhout, M. H.; Price, A. T. J. Org. Chem. 1994, 59, 1418. Hertzog, D. L.; Austin, D. J.; Nadler, W. R.; Padwa, A. Tetrahedron Lett. 1992, 33, 4731.
11. Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123. Padwa, A.; Marino, J. P., Jr.; Osterhout, M. H. J. Org. Chem. 1995, 60, 2704. Padwa, A.; Hertzog, D. L; Nadler, W. R. J. Org. Chem. 1994, 59, 7072. Marino, J. P., Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A.; Padwa, A. J. Org. Chem. 1994, 59, 5518. Padwa, A.; Hertzog, D. L.; Nadler, W. R.; Osterhout, M. H.; Price, A. T. J. Org. Chem. 1994, 59, 1418. Hertzog, D. L.; Austin, D. J.; Nadler, W. R.; Padwa, A. Tetrahedron Lett. 1992, 33, 4731.
12. Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123. Padwa, A.; Marino, J. P., Jr.; Osterhout, M. H. J. Org. Chem. 1995, 60, 2704. Padwa, A.; Hertzog, D. L; Nadler, W. R. J. Org. Chem. 1994, 59, 7072. Marino, J. P., Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A.; Padwa, A. J. Org. Chem. 1994, 59, 5518. Padwa, A.; Hertzog, D. L.; Nadler, W. R.; Osterhout, M. H.; Price, A. T. J. Org. Chem. 1994, 59, 1418. Hertzog, D. L.; Austin, D. J.; Nadler, W. R.; Padwa, A. Tetrahedron Lett. 1992, 33, 4731.
13. Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123. Padwa, A.; Marino, J. P., Jr.; Osterhout, M. H. J. Org. Chem. 1995, 60, 2704. Padwa, A.; Hertzog, D. L; Nadler, W. R. J. Org. Chem. 1994, 59, 7072. Marino, J. P., Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A.; Padwa, A. J. Org. Chem. 1994, 59, 5518. Padwa, A.; Hertzog, D. L.; Nadler, W. R.; Osterhout, M. H.; Price, A. T. J. Org. Chem. 1994, 59, 1418. Hertzog, D. L.; Austin, D. J.; Nadler, W. R.; Padwa, A. Tetrahedron Lett. 1992, 33, 4731.
14. Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123. Padwa, A.; Marino, J. P., Jr.; Osterhout, M. H. J. Org. Chem. 1995, 60, 2704. Padwa, A.; Hertzog, D. L; Nadler, W. R. J. Org. Chem. 1994, 59, 7072. Marino, J. P., Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A.; Padwa, A. J. Org. Chem. 1994, 59, 5518. Padwa, A.; Hertzog, D. L.; Nadler, W. R.; Osterhout, M. H.; Price, A. T. J. Org. Chem. 1994, 59, 1418. Hertzog, D. L.; Austin, D. J.; Nadler, W. R.; Padwa, A. Tetrahedron Lett. 1992, 33, 4731.
15. Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123. Padwa, A.; Marino, J. P., Jr.; Osterhout, M. H. J. Org. Chem. 1995, 60, 2704. Padwa, A.; Hertzog, D. L; Nadler, W. R. J. Org. Chem. 1994, 59, 7072. Marino, J. P., Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A.; Padwa, A. J. Org. Chem. 1994, 59, 5518. Padwa, A.; Hertzog, D. L.; Nadler, W. R.; Osterhout, M. H.; Price, A. T. J. Org. Chem. 1994, 59, 1418. Hertzog, D. L.; Austin, D. J.; Nadler, W. R.; Padwa, A. Tetrahedron Lett. 1992, 33, 4731.
16. For a review on triflate chemistry, see: Ritter, K. Synthesis 1993, 735.
17. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.
18. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.
19. Hart, N. K.; Johns, S. R.; Lamberton, J. A. Aust. J. Chem. 1968, 21, 2579.
20. Wick, A. E.; Bartlett, P. A.; Dolphin, D. Helv. Chim. Acta 1971, 54, 513.
21. Regitz, M.; Maas, G. Diazo Compounds: Properties and Synthesis; Academic Press: Orlando, FL, 1986; p 185.
22. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979.
23. De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
24. For a review on organometallic coupling reactions of enol Inflates, see: Scott, W. J.; McMurry, J. E. Acc. Chem. Res. 1988, 21, 47.
25. Cacchi, S.; Morera, E.; Ortar, G. Tetrahedron Lett. 1984, 42, 4821.
26. For some alternate syntheses of (±)-ipalbidine see: Danishefsky, S. J.; Vogel, C. J. Org. Chem. 1986, 51, 3916. Iida, H.; Watanabe, Y.; Kibayashi, C. J. Chem. Soc., Perkin Trans. 1 1985, 261. Cragg, J. E.; Hedeges, S. H.; Herbert, R. B. Tetrahedron Lett. 1981, 22, 2127. Howard, A. S.; Gerrans, G. C.; Micael, J. P. J. Org. Chem. 1980, 45, 1713. Hedeges, S. H.; Herbert, R. B. J. Chem. Res., Synop. 1979, 1, 413. Stevens, R. V.; Luh, Y. Tetrahedron Lett. 1977, 979. Govindachari, T. R.; Sidhaye, A. R.; Viswanathan, N. Tetrahedron 1970, 26, 3829.
27. For some alternate syntheses of (±)-ipalbidine see: Danishefsky, S. J.; Vogel, C. J. Org. Chem. 1986, 51, 3916. Iida, H.; Watanabe, Y.; Kibayashi, C. J. Chem. Soc., Perkin Trans. 1 1985, 261. Cragg, J. E.; Hedeges, S. H.; Herbert, R. B. Tetrahedron Lett. 1981, 22, 2127. Howard, A. S.; Gerrans, G. C.; Micael, J. P. J. Org. Chem. 1980, 45, 1713. Hedeges, S. H.; Herbert, R. B. J. Chem. Res., Synop. 1979, 1, 413. Stevens, R. V.; Luh, Y. Tetrahedron Lett. 1977, 979. Govindachari, T. R.; Sidhaye, A. R.; Viswanathan, N. Tetrahedron 1970, 26, 3829.
28. For some alternate syntheses of (±)-ipalbidine see: Danishefsky, S. J.; Vogel, C. J. Org. Chem. 1986, 51, 3916. Iida, H.; Watanabe, Y.; Kibayashi, C. J. Chem. Soc., Perkin Trans. 1 1985, 261. Cragg, J. E.; Hedeges, S. H.; Herbert, R. B. Tetrahedron Lett. 1981, 22, 2127. Howard, A. S.; Gerrans, G. C.; Micael, J. P. J. Org. Chem. 1980, 45, 1713. Hedeges, S. H.; Herbert, R. B. J. Chem. Res., Synop. 1979, 1, 413. Stevens, R. V.; Luh, Y. Tetrahedron Lett. 1977, 979. Govindachari, T. R.; Sidhaye, A. R.; Viswanathan, N. Tetrahedron 1970, 26, 3829.
29. For some alternate syntheses of (±)-ipalbidine see: Danishefsky, S. J.; Vogel, C. J. Org. Chem. 1986, 51, 3916. Iida, H.; Watanabe, Y.; Kibayashi, C. J. Chem. Soc., Perkin Trans. 1 1985, 261. Cragg, J. E.; Hedeges, S. H.; Herbert, R. B. Tetrahedron Lett. 1981, 22, 2127. Howard, A. S.; Gerrans, G. C.; Micael, J. P. J. Org. Chem. 1980, 45, 1713. Hedeges, S. H.; Herbert, R. B. J. Chem. Res., Synop. 1979, 1, 413. Stevens, R. V.; Luh, Y. Tetrahedron Lett. 1977, 979. Govindachari, T. R.; Sidhaye, A. R.; Viswanathan, N. Tetrahedron 1970, 26, 3829.
30. For some alternate syntheses of (±)-ipalbidine see: Danishefsky, S. J.; Vogel, C. J. Org. Chem. 1986, 51, 3916. Iida, H.; Watanabe, Y.; Kibayashi, C. J. Chem. Soc., Perkin Trans. 1 1985, 261. Cragg, J. E.; Hedeges, S. H.; Herbert, R. B. Tetrahedron Lett. 1981, 22, 2127. Howard, A. S.; Gerrans, G. C.; Micael, J. P. J. Org. Chem. 1980, 45, 1713. Hedeges, S. H.; Herbert, R. B. J. Chem. Res., Synop. 1979, 1, 413. Stevens, R. V.; Luh, Y. Tetrahedron Lett. 1977, 979. Govindachari, T. R.; Sidhaye, A. R.; Viswanathan, N. Tetrahedron 1970, 26, 3829.
31. For some alternate syntheses of (±)-ipalbidine see: Danishefsky, S. J.; Vogel, C. J. Org. Chem. 1986, 51, 3916. Iida, H.; Watanabe, Y.; Kibayashi, C. J. Chem. Soc., Perkin Trans. 1 1985, 261. Cragg, J. E.; Hedeges, S. H.; Herbert, R. B. Tetrahedron Lett. 1981, 22, 2127. Howard, A. S.; Gerrans, G. C.; Micael, J. P. J. Org. Chem. 1980, 45, 1713. Hedeges, S. H.; Herbert, R. B. J. Chem. Res., Synop. 1979, 1, 413. Stevens, R. V.; Luh, Y. Tetrahedron Lett. 1977, 979. Govindachari, T. R.; Sidhaye, A. R.; Viswanathan, N. Tetrahedron 1970, 26, 3829.
32. For some alternate syntheses of (±)-ipalbidine see: Danishefsky, S. J.; Vogel, C. J. Org. Chem. 1986, 51, 3916. Iida, H.; Watanabe, Y.; Kibayashi, C. J. Chem. Soc., Perkin Trans. 1 1985, 261. Cragg, J. E.; Hedeges, S. H.; Herbert, R. B. Tetrahedron Lett. 1981, 22, 2127. Howard, A. S.; Gerrans, G. C.; Micael, J. P. J. Org. Chem. 1980, 45, 1713. Hedeges, S. H.; Herbert, R. B. J. Chem. Res., Synop. 1979, 1, 413. Stevens, R. V.; Luh, Y. Tetrahedron Lett. 1977, 979. Govindachari, T. R.; Sidhaye, A. R.; Viswanathan, N. Tetrahedron 1970, 26, 3829.
33. Stille, J. K.; Echavarren, A. M.; Williams, R. M.; Hendrix, J. A. Organic Synthesis; Overman, L. E., Ed.; Wiley and Sons: New York, 1993; Vol. 71, p 97.