A versatile synthetic route to indolizidines, (+)-7-deoxy-6- epicastanospermine, (-)-7,8-dideoxy-6-epicastanospermine and (-)-N- acetylslaframine

Tetrahedron Letters

Volumn 39, Issue 49, 1998, Pages 9047-9050

  Kang, Sung Ho ^a   Kim, Joon Seop ^a   Youn, Joo Hack ^b  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b SunMoon University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLIZINE DERIVATIVE; SPERMINE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0032481080     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02051-6     Document Type: Article

References (36)

1. 1. Elbein, A. D.; Molyneux, R. J. In Alkaloids: Chemical and Biological Perspectives, ed. Pelletier, S. W. Wiley, New York, 1987, vol. 5, Chaper 1; Nishimura, Y. In Studies in Natural Products Chemistry, ed. Atta-ur-Rahman, Elsevier, Amsterdam, 1992, vol. 10, pp 495-583; Michael, J. P. Nat. Prod. Rep. 1995, 12, 77-89.
2. 1. Elbein, A. D.; Molyneux, R. J. In Alkaloids: Chemical and Biological Perspectives, ed. Pelletier, S. W. Wiley, New York, 1987, vol. 5, Chaper 1; Nishimura, Y. In Studies in Natural Products Chemistry, ed. Atta-ur-Rahman, Elsevier, Amsterdam, 1992, vol. 10, pp 495-583; Michael, J. P. Nat. Prod. Rep. 1995, 12, 77-89.
3. 1. Elbein, A. D.; Molyneux, R. J. In Alkaloids: Chemical and Biological Perspectives, ed. Pelletier, S. W. Wiley, New York, 1987, vol. 5, Chaper 1; Nishimura, Y. In Studies in Natural Products Chemistry, ed. Atta-ur-Rahman, Elsevier, Amsterdam, 1992, vol. 10, pp 495-583; Michael, J. P. Nat. Prod. Rep. 1995, 12, 77-89.
4. 2. Burgess, K.; Henderson, I. Tetrahedron, 1992, 48, 4045-4066. For recent references, see: Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547-550; Mootoo, D. R.; Zhao, H. J. Org. Chem. 1996, 61, 6762-6763; Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217-7221.
5. 2. Burgess, K.; Henderson, I. Tetrahedron, 1992, 48, 4045-4066. For recent references, see: Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547-550; Mootoo, D. R.; Zhao, H. J. Org. Chem. 1996, 61, 6762-6763; Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217-7221.
6. 2. Burgess, K.; Henderson, I. Tetrahedron, 1992, 48, 4045-4066. For recent references, see: Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547-550; Mootoo, D. R.; Zhao, H. J. Org. Chem. 1996, 61, 6762-6763; Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217-7221.
7. 2. Burgess, K.; Henderson, I. Tetrahedron, 1992, 48, 4045-4066. For recent references, see: Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547-550; Mootoo, D. R.; Zhao, H. J. Org. Chem. 1996, 61, 6762-6763; Pearson, W. H.; Hembre, E. J. J. Org. Chem. 1996, 61, 7217-7221.
8. 3. Molyneux, R. J.; Tropea, J. E.; Elbein, A. D. J. Nat. Prod. 1990, 53, 609-614.
9. 4. Rainey, D. P.; Smalley, E. B.; Crump, M. H.; Strong, F. M. Nature (London), 1965, 205, 203-204; Aust, S. D; Broquist, H. P. Nature (London), 1965, 205, 204; Aust, S. D.; Broquist, H. P.; Rinehart, K. L. Jr. J. Am. Chem. Soc. 1966, 88, 2879-2880; Whitlock, B. J.; Rainey, D. P.; Riggs, N. V.; Strong, F. M. Tetrahedron Lett. 1966, 3819-3824; Gardiner, R. A.; Rinehart, K. L. Jr.; Snyder, J. J.; Broquist, H. P. J. Am. Chem. Soc. 1968, 90, 5639-5640.
10. 4. Rainey, D. P.; Smalley, E. B.; Crump, M. H.; Strong, F. M. Nature (London), 1965, 205, 203-204; Aust, S. D; Broquist, H. P. Nature (London), 1965, 205, 204; Aust, S. D.; Broquist, H. P.; Rinehart, K. L. Jr. J. Am. Chem. Soc. 1966, 88, 2879-2880; Whitlock, B. J.; Rainey, D. P.; Riggs, N. V.; Strong, F. M. Tetrahedron Lett. 1966, 3819-3824; Gardiner, R. A.; Rinehart, K. L. Jr.; Snyder, J. J.; Broquist, H. P. J. Am. Chem. Soc. 1968, 90, 5639-5640.
11. 4. Rainey, D. P.; Smalley, E. B.; Crump, M. H.; Strong, F. M. Nature (London), 1965, 205, 203-204; Aust, S. D; Broquist, H. P. Nature (London), 1965, 205, 204; Aust, S. D.; Broquist, H. P.; Rinehart, K. L. Jr. J. Am. Chem. Soc. 1966, 88, 2879-2880; Whitlock, B. J.; Rainey, D. P.; Riggs, N. V.; Strong, F. M. Tetrahedron Lett. 1966, 3819-3824; Gardiner, R. A.; Rinehart, K. L. Jr.; Snyder, J. J.; Broquist, H. P. J. Am. Chem. Soc. 1968, 90, 5639-5640.
12. 4. Rainey, D. P.; Smalley, E. B.; Crump, M. H.; Strong, F. M. Nature (London), 1965, 205, 203-204; Aust, S. D; Broquist, H. P. Nature (London), 1965, 205, 204; Aust, S. D.; Broquist, H. P.; Rinehart, K. L. Jr. J. Am. Chem. Soc. 1966, 88, 2879-2880; Whitlock, B. J.; Rainey, D. P.; Riggs, N. V.; Strong, F. M. Tetrahedron Lett. 1966, 3819-3824; Gardiner, R. A.; Rinehart, K. L. Jr.; Snyder, J. J.; Broquist, H. P. J. Am. Chem. Soc. 1968, 90, 5639-5640.
13. 4. Rainey, D. P.; Smalley, E. B.; Crump, M. H.; Strong, F. M. Nature (London), 1965, 205, 203-204; Aust, S. D; Broquist, H. P. Nature (London), 1965, 205, 204; Aust, S. D.; Broquist, H. P.; Rinehart, K. L. Jr. J. Am. Chem. Soc. 1966, 88, 2879-2880; Whitlock, B. J.; Rainey, D. P.; Riggs, N. V.; Strong, F. M. Tetrahedron Lett. 1966, 3819-3824; Gardiner, R. A.; Rinehart, K. L. Jr.; Snyder, J. J.; Broquist, H. P. J. Am. Chem. Soc. 1968, 90, 5639-5640.
14. 5. Broquist, H. P.; Snyder, J. J. In Microbial Toxins, eds. Ajl, S. J.; Kadis, S.; Montie, T. C. Academic, New York, 1971, pp 317-333; Guengerich, F. P.; Broquist, H. P. In Bioorganic Chemistry, ed. van Tamelen, E. E. Academic, New York, 1979, vol.2, pp 97-109.
15. 5. Broquist, H. P.; Snyder, J. J. In Microbial Toxins, eds. Ajl, S. J.; Kadis, S.; Montie, T. C. Academic, New York, 1971, pp 317-333; Guengerich, F. P.; Broquist, H. P. In Bioorganic Chemistry, ed. van Tamelen, E. E. Academic, New York, 1979, vol.2, pp 97-109.
16. 6. Broquist, H. P. Ann. Rev. Nutr. 1985, 5, 391-409.
17. 7. Bongini, A.; Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. J. Org. Chem. 1986, 51, 4905-4910; Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049-5052; Kang, S. H.; Choi, H.-w. J. Chem. Soc. Chem. Commun. 1996, 1521-1522; Kang, S. H.; Kim, G. T.; Yoo, Y. S. Tetrahedron Lett. 1997, 38, 603-606.
18. 7. Bongini, A.; Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. J. Org. Chem. 1986, 51, 4905-4910; Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049-5052; Kang, S. H.; Choi, H.-w. J. Chem. Soc. Chem. Commun. 1996, 1521-1522; Kang, S. H.; Kim, G. T.; Yoo, Y. S. Tetrahedron Lett. 1997, 38, 603-606.
19. 7. Bongini, A.; Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. J. Org. Chem. 1986, 51, 4905-4910; Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049-5052; Kang, S. H.; Choi, H.-w. J. Chem. Soc. Chem. Commun. 1996, 1521-1522; Kang, S. H.; Kim, G. T.; Yoo, Y. S. Tetrahedron Lett. 1997, 38, 603-606.
20. 7. Bongini, A.; Cardillo, G.; Orena, M.; Sandri, S.; Tomasini, C. J. Org. Chem. 1986, 51, 4905-4910; Kang, S. H.; Kim, G. T. Tetrahedron Lett. 1995, 36, 5049-5052; Kang, S. H.; Choi, H.-w. J. Chem. Soc. Chem. Commun. 1996, 1521-1522; Kang, S. H.; Kim, G. T.; Yoo, Y. S. Tetrahedron Lett. 1997, 38, 603-606.
21. 8. For recent synthesis of (-)-slaframine, see: a) Hua, D. H.; Park, J.-G.; Katsuhira, T.; Bharathi, S. N. J. Org. Chem. 1993, 58, 2144-2150;
22. b) Szeto, P.; Lathbury, D. C.; Gallagher, T. Tetrahedron Lett. 1995, 36, 6957-6960;
23. c) Knight, D. W.; Sibley, A. W. J. Chem. Soc. Perkin Trans, 1, 1997, 2179-2187.
24. 9. Lane, C. F.; Myatt, H. L.; Daniels, J.; Hopps, H. B. J. Org. Chem. 1974, 39, 3052-3054ss.
25. 10. Mancuso, A. J.; Swern, D. Synthesis, 1981, 165-185.
26. 11. Kang, S. H.; Hwang, T. S.; Lim, J. K.; Kim, W. J. Bull. Korean Chem. Soc. 1990, 11, 455-460.
27. 12. Mitsunobu, O. Synthesis, 1981, 1-28.
28. 13. Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K.; Utimoto, K. Bull.Chem. Soc. Jpn. 1989, 62, 143-147.
29. 2, found 157.1122.
30. 15. McGarvey, G. J.; Williams, J. M.; Hiner, R. N.; Matsubara, Y.; Oh, T. J. Am. Chem. Soc. 1986, 108, 4943-4952.
31. 16. Wasserman, H. H.; Berger, G. D.; Cho, K. R. Tetrahedron, 1983, 39, 2459-2464; Rawal, V. H.; Cava, M. P. Tetrahedron Lett. 1985, 26, 6141-6142.
32. 16. Wasserman, H. H.; Berger, G. D.; Cho, K. R. Tetrahedron, 1983, 39, 2459-2464; Rawal, V. H.; Cava, M. P. Tetrahedron Lett. 1985, 26, 6141-6142.
33. 17. Pearson, W. H.; Bergmeier, S. C.; Williams, J. P. J. Org. Chem. 1992, 57, 3977-3987.
34. 18. Harris, C. M.; Schneider, M. J.; Ugemach, F. S.; Hill, J. E.; Harris, T. M. J. Am. Chem. Soc. 1988, 110, 940-949; Knapp, S.; Gibson, F. S. J. Org. Chem. 1992, 57, 4802-4809.
35. 18. Harris, C. M.; Schneider, M. J.; Ugemach, F. S.; Hill, J. E.; Harris, T. M. J. Am. Chem. Soc. 1988, 110, 940-949; Knapp, S.; Gibson, F. S. J. Org. Chem. 1992, 57, 4802-4809.
36. 19. All new compounds showed satisfactory spectral data.