A New Method for the Formation of Octahydroindole Alkaloids via the Intramolecular Diels-Alder Reaction of 2-Amidofurans

Journal of Organic Chemistry

Volumn 63, Issue 16, 1998, Pages 5304-5305

  Padwa, Albert ^a   Brodney, Michael A ^a   Dimitroff, Martin ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000880225     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980815e     Document Type: Article

References (25)

1. Martin, S. F. In The Alkaloids; Brossi, A., Ed.; Academic Press Inc.: New York, 1987; Vol. 30, pp 251-377. Lewis, J. R. Nat. Prod. Rep. 1994, 11, 329. Jeffs, P. W. In The Alkaloids; Rodrigo, R. G. A., Ed.; Academic Press: New York, 1981; Vol. 19, pp 1-80.
2. Martin, S. F. In The Alkaloids; Brossi, A., Ed.; Academic Press Inc.: New York, 1987; Vol. 30, pp 251-377. Lewis, J. R. Nat. Prod. Rep. 1994, 11, 329. Jeffs, P. W. In The Alkaloids; Rodrigo, R. G. A., Ed.; Academic Press: New York, 1981; Vol. 19, pp 1-80.
3. Martin, S. F. In The Alkaloids; Brossi, A., Ed.; Academic Press Inc.: New York, 1987; Vol. 30, pp 251-377. Lewis, J. R. Nat. Prod. Rep. 1994, 11, 329. Jeffs, P. W. In The Alkaloids; Rodrigo, R. G. A., Ed.; Academic Press: New York, 1981; Vol. 19, pp 1-80.
4. For some leading references, see: Banwell, M. G.; Wu, A. W. J. Chem. Soc., Perkin Trans. 1 1994, 2671. Grothjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993, 579. Pearson, W. H.; Schkeryantz, J. M. J. Org. Chem. 1992, 57, 6783. Backvall, J. E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem. 1991, 56, 2988. Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536. Stork, G.; Mah, R. Heterocycles 1989, 28, 723.
5. For some leading references, see: Banwell, M. G.; Wu, A. W. J. Chem. Soc., Perkin Trans. 1 1994, 2671. Grothjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993, 579. Pearson, W. H.; Schkeryantz, J. M. J. Org. Chem. 1992, 57, 6783. Backvall, J. E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem. 1991, 56, 2988. Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536. Stork, G.; Mah, R. Heterocycles 1989, 28, 723.
6. For some leading references, see: Banwell, M. G.; Wu, A. W. J. Chem. Soc., Perkin Trans. 1 1994, 2671. Grothjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993, 579. Pearson, W. H.; Schkeryantz, J. M. J. Org. Chem. 1992, 57, 6783. Backvall, J. E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem. 1991, 56, 2988. Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536. Stork, G.; Mah, R. Heterocycles 1989, 28, 723.
7. For some leading references, see: Banwell, M. G.; Wu, A. W. J. Chem. Soc., Perkin Trans. 1 1994, 2671. Grothjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993, 579. Pearson, W. H.; Schkeryantz, J. M. J. Org. Chem. 1992, 57, 6783. Backvall, J. E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem. 1991, 56, 2988. Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536. Stork, G.; Mah, R. Heterocycles 1989, 28, 723.
8. For some leading references, see: Banwell, M. G.; Wu, A. W. J. Chem. Soc., Perkin Trans. 1 1994, 2671. Grothjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993, 579. Pearson, W. H.; Schkeryantz, J. M. J. Org. Chem. 1992, 57, 6783. Backvall, J. E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem. 1991, 56, 2988. Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536. Stork, G.; Mah, R. Heterocycles 1989, 28, 723.
9. For some leading references, see: Banwell, M. G.; Wu, A. W. J. Chem. Soc., Perkin Trans. 1 1994, 2671. Grothjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993, 579. Pearson, W. H.; Schkeryantz, J. M. J. Org. Chem. 1992, 57, 6783. Backvall, J. E.; Andersson, P. G.; Stone, G. B.; Gogoll, A. J. Org. Chem. 1991, 56, 2988. Jolly, R. S.; Livinghouse, T. J. Am. Chem. Soc. 1988, 110, 7536. Stork, G.; Mah, R. Heterocycles 1989, 28, 723.
10. For some leading references concerning the intramolecular Diels-Alder reaction of furans (IMDAF), see: Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179. Sternbach, D. D.; Rossana, D. M.; Onon, K. D. J. Org. Chem. 1984, 49, 3427. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1989, 111, 5469.
11. For some leading references concerning the intramolecular Diels-Alder reaction of furans (IMDAF), see: Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179. Sternbach, D. D.; Rossana, D. M.; Onon, K. D. J. Org. Chem. 1984, 49, 3427. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1989, 111, 5469.
12. For some leading references concerning the intramolecular Diels-Alder reaction of furans (IMDAF), see: Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179. Sternbach, D. D.; Rossana, D. M.; Onon, K. D. J. Org. Chem. 1984, 49, 3427. Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1989, 111, 5469.
13. Aimi, N.; Goto, T.; Irie, H.; Ishii, H.; Ito, S.; Kodama, M.; Natori, S.; Oishi, T.; Sakai, S.; Yamazaki, M. In Natural Products Chemistry; Nakanishi, K., Goto, T., Ito, S., Natori, S., Nozoe, S., Eds.; Academic Press: New York, 1975; Vol. 2, pp 257-261.
14. Dalton, D. R. The Alkaloids: Fundamental Chemistry. A Biogenetic Approach; Marcel Dekker: New York, 1979.
15. Husson, H. P. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. D., Eds.; Wiley: New York, 1983; Vol. 25, Part IV, pp 293-330.
16. Padwa, A.; Dimitroff, M.; Waterson, A. G.; Wu, T. J. Org. Chem. 1997, 62, 4088; 1998, 63, 3986.
17. Padwa, A.; Dimitroff, M.; Waterson, A. G.; Wu, T. J. Org. Chem. 1997, 62, 4088; 1998, 63, 3986.
18. For an earlier example of an IMDAF reaction of a nitrogen-substituted furan, see: Himbert, G.; Schlindwein, H. J. Liebigs Ann. Recl. 1997, 435.
19. Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177. Overman, L. E. Pure Appl. Chem. 1994, 66, 1423.
20. Grigg, R.; Santhakumar, V.; Sridharan, V.; Thornton-Pett, M.; Bridge, A. W. Tetrahedron 1993, 49, 5177. Overman, L. E. Pure Appl. Chem. 1994, 66, 1423.
21. Rigby, J. H.; Hughes, R. C.; Heeg, M. J. J. Am. Chem. Soc. 1995, 117, 7834.
22. Jeffrey, T. J. Chem. Soc., Chem. Commun. 1984, 1287. Jeffrey, T. Synthesis 1987, 70.
23. Jeffrey, T. J. Chem. Soc., Chem. Commun. 1984, 1287. Jeffrey, T. Synthesis 1987, 70.
24. We wish to thank Professor Jim Rigby for providing experimental conditions for the endo cyclization of enamide 16. (13) For several pertinent references dealing with some successful total and formal syntheses of (±)-dendrobine, see: Sha, C. K.; Chiu, R. T.; Yang, C. F.; Yao, N. T.; Tseng, W. H.; Liao, F. L.; Wang, S. L. J. Am. Chem. Soc. 1997, 119, 4130.
25. Martin, S. F.; Li, W. J. Org. Chem. 1991, 56, 642.