A flexible approach toward trisubstituted piperidines and indolizidines: Synthesis of 6-epi-indolizidine 223A

Journal of Organic Chemistry

Volumn 68, Issue 11, 2003, Pages 4371-4381

  Harris, Joel M ^a   Padwa, Albert ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOPHILES;

ISOMERS; OXIDATION; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

NITROGEN COMPOUNDS;

INDOLIZIDINE ALKALOID; PIPERIDINE DERIVATIVE;

ARTICLE; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

ALKALOIDS; ANIMALS; ANURA; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; INDICATORS AND REAGENTS; INDOLIZINES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PIPERIDINES; STEREOISOMERISM;

EID: 0038441525     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034324s     Document Type: Article

References (104)

1. Roth, H. J.; Kleeman, A. Pharmaceutical Chemistry; John Wiley and Sons: New York, 1988. Elbein, A. D.; Molyneux, R. In Alkaloids, Chemical and Biological Perspectives; Pelletier, W., Ed.; John Wiley and Sons: New York, 1987; Vol. 57, p 1. Gogfraid, T.; Miller, R.; Wibo, M. Pharmacol. Rev. 1986, 38, 321.
2. Roth, H. J.; Kleeman, A. Pharmaceutical Chemistry; John Wiley and Sons: New York, 1988. Elbein, A. D.; Molyneux, R. In Alkaloids, Chemical and Biological Perspectives; Pelletier, W., Ed.; John Wiley and Sons: New York, 1987; Vol. 57, p 1. Gogfraid, T.; Miller, R.; Wibo, M. Pharmacol. Rev. 1986, 38, 321.
3. Roth, H. J.; Kleeman, A. Pharmaceutical Chemistry; John Wiley and Sons: New York, 1988. Elbein, A. D.; Molyneux, R. In Alkaloids, Chemical and Biological Perspectives; Pelletier, W., Ed.; John Wiley and Sons: New York, 1987; Vol. 57, p 1. Gogfraid, T.; Miller, R.; Wibo, M. Pharmacol. Rev. 1986, 38, 321.
4. Dewick, P. M. In Medicinal Natural Products; J. Wiley & Sons: Chichester, UK, 1997; Chapter 6. Pichon, M.; Figadere, B. Tetrahedron: Asymmetry 1996, 7, 927 and references therein. Yus, M.; Foubelo, F. J. Org. Chem. 2001, 66, 6207. Hill, K. R. Chem. Alkaloids 1970, 385. Laschat, S.; Dickner, T. Synthesis 2000, 13, 1781. Laschat, S. Liebigs Ann. 1997, 1, 1. Wang, C. J. J.; Wuonola, M. A. Org. Prep. Proced. Int. 1992, 24, 583. Baliah, V.; Jeyaraman, R.; Chandrasekaran, L. Chem. Rev. 1983, 83, 379.
5. Dewick, P. M. In Medicinal Natural Products; J. Wiley & Sons: Chichester, UK, 1997; Chapter 6. Pichon, M.; Figadere, B. Tetrahedron: Asymmetry 1996, 7, 927 and references therein. Yus, M.; Foubelo, F. J. Org. Chem. 2001, 66, 6207. Hill, K. R. Chem. Alkaloids 1970, 385. Laschat, S.; Dickner, T. Synthesis 2000, 13, 1781. Laschat, S. Liebigs Ann. 1997, 1, 1. Wang, C. J. J.; Wuonola, M. A. Org. Prep. Proced. Int. 1992, 24, 583. Baliah, V.; Jeyaraman, R.; Chandrasekaran, L. Chem. Rev. 1983, 83, 379.
6. Dewick, P. M. In Medicinal Natural Products; J. Wiley & Sons: Chichester, UK, 1997; Chapter 6. Pichon, M.; Figadere, B. Tetrahedron: Asymmetry 1996, 7, 927 and references therein. Yus, M.; Foubelo, F. J. Org. Chem. 2001, 66, 6207. Hill, K. R. Chem. Alkaloids 1970, 385. Laschat, S.; Dickner, T. Synthesis 2000, 13, 1781. Laschat, S. Liebigs Ann. 1997, 1, 1. Wang, C. J. J.; Wuonola, M. A. Org. Prep. Proced. Int. 1992, 24, 583. Baliah, V.; Jeyaraman, R.; Chandrasekaran, L. Chem. Rev. 1983, 83, 379.
7. Dewick, P. M. In Medicinal Natural Products; J. Wiley & Sons: Chichester, UK, 1997; Chapter 6. Pichon, M.; Figadere, B. Tetrahedron: Asymmetry 1996, 7, 927 and references therein. Yus, M.; Foubelo, F. J. Org. Chem. 2001, 66, 6207. Hill, K. R. Chem. Alkaloids 1970, 385. Laschat, S.; Dickner, T. Synthesis 2000, 13, 1781. Laschat, S. Liebigs Ann. 1997, 1, 1. Wang, C. J. J.; Wuonola, M. A. Org. Prep. Proced. Int. 1992, 24, 583. Baliah, V.; Jeyaraman, R.; Chandrasekaran, L. Chem. Rev. 1983, 83, 379.
8. Dewick, P. M. In Medicinal Natural Products; J. Wiley & Sons: Chichester, UK, 1997; Chapter 6. Pichon, M.; Figadere, B. Tetrahedron: Asymmetry 1996, 7, 927 and references therein. Yus, M.; Foubelo, F. J. Org. Chem. 2001, 66, 6207. Hill, K. R. Chem. Alkaloids 1970, 385. Laschat, S.; Dickner, T. Synthesis 2000, 13, 1781. Laschat, S. Liebigs Ann. 1997, 1, 1. Wang, C. J. J.; Wuonola, M. A. Org. Prep. Proced. Int. 1992, 24, 583. Baliah, V.; Jeyaraman, R.; Chandrasekaran, L. Chem. Rev. 1983, 83, 379.
9. Dewick, P. M. In Medicinal Natural Products; J. Wiley & Sons: Chichester, UK, 1997; Chapter 6. Pichon, M.; Figadere, B. Tetrahedron: Asymmetry 1996, 7, 927 and references therein. Yus, M.; Foubelo, F. J. Org. Chem. 2001, 66, 6207. Hill, K. R. Chem. Alkaloids 1970, 385. Laschat, S.; Dickner, T. Synthesis 2000, 13, 1781. Laschat, S. Liebigs Ann. 1997, 1, 1. Wang, C. J. J.; Wuonola, M. A. Org. Prep. Proced. Int. 1992, 24, 583. Baliah, V.; Jeyaraman, R.; Chandrasekaran, L. Chem. Rev. 1983, 83, 379.
10. Dewick, P. M. In Medicinal Natural Products; J. Wiley & Sons: Chichester, UK, 1997; Chapter 6. Pichon, M.; Figadere, B. Tetrahedron: Asymmetry 1996, 7, 927 and references therein. Yus, M.; Foubelo, F. J. Org. Chem. 2001, 66, 6207. Hill, K. R. Chem. Alkaloids 1970, 385. Laschat, S.; Dickner, T. Synthesis 2000, 13, 1781. Laschat, S. Liebigs Ann. 1997, 1, 1. Wang, C. J. J.; Wuonola, M. A. Org. Prep. Proced. Int. 1992, 24, 583. Baliah, V.; Jeyaraman, R.; Chandrasekaran, L. Chem. Rev. 1983, 83, 379.
11. Dewick, P. M. In Medicinal Natural Products; J. Wiley & Sons: Chichester, UK, 1997; Chapter 6. Pichon, M.; Figadere, B. Tetrahedron: Asymmetry 1996, 7, 927 and references therein. Yus, M.; Foubelo, F. J. Org. Chem. 2001, 66, 6207. Hill, K. R. Chem. Alkaloids 1970, 385. Laschat, S.; Dickner, T. Synthesis 2000, 13, 1781. Laschat, S. Liebigs Ann. 1997, 1, 1. Wang, C. J. J.; Wuonola, M. A. Org. Prep. Proced. Int. 1992, 24, 583. Baliah, V.; Jeyaraman, R.; Chandrasekaran, L. Chem. Rev. 1983, 83, 379.
12. Ikeda, M.; Sato, T.; Ishibashi, H. Heterocycles 1988, 27, 1465. Robins, D. J. Nat. Prod. Rep. 1995, 12, 413. Michael, J. P. Nat. Prod. Rep. 1997, 14, 619.
13. Ikeda, M.; Sato, T.; Ishibashi, H. Heterocycles 1988, 27, 1465. Robins, D. J. Nat. Prod. Rep. 1995, 12, 413. Michael, J. P. Nat. Prod. Rep. 1997, 14, 619.
14. Ikeda, M.; Sato, T.; Ishibashi, H. Heterocycles 1988, 27, 1465. Robins, D. J. Nat. Prod. Rep. 1995, 12, 413. Michael, J. P. Nat. Prod. Rep. 1997, 14, 619.
15. Bosch, J.; Bonjoch, J. Studies in Natural Product Chemistry; Rahman, A. U., Ed.; Elseview: New York, 1988; Vol. 1, p 31. O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435-446. Bailey, P. D.; Millwood, P. A.; Smith, P. D. Chem. Commun. 1998, 6, 633.
16. Bosch, J.; Bonjoch, J. Studies in Natural Product Chemistry; Rahman, A. U., Ed.; Elseview: New York, 1988; Vol. 1, p 31. O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435-446. Bailey, P. D.; Millwood, P. A.; Smith, P. D. Chem. Commun. 1998, 6, 633.
17. Bosch, J.; Bonjoch, J. Studies in Natural Product Chemistry; Rahman, A. U., Ed.; Elseview: New York, 1988; Vol. 1, p 31. O'Hagan, D. Nat. Prod. Rep. 2000, 17, 435-446. Bailey, P. D.; Millwood, P. A.; Smith, P. D. Chem. Commun. 1998, 6, 633.
18. For recent reviews, see: Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825. Lekevits, E. Chem. Heterocycl. Compd. 1995, 31, 639.
19. For recent reviews, see: Sardina, F. J.; Rapoport, H. Chem. Rev. 1996, 96, 1825. Lekevits, E. Chem. Heterocycl. Compd. 1995, 31, 639.
20. Chutian, S.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. Enders, D.; Thiebes, C. Pure Appl. Chem. 2001, 73, 573. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, E. J., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 2, p 251. Laschat, S.; Dickner, T. Synthesis 2000, 1781. Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. Amat, M.; Perez, M.; Nuria, L.; Bosch, J.; Lago, E.; Molins, E. Org. Lett. 2001, 3, 611.
21. Chutian, S.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. Enders, D.; Thiebes, C. Pure Appl. Chem. 2001, 73, 573. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, E. J., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 2, p 251. Laschat, S.; Dickner, T. Synthesis 2000, 1781. Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. Amat, M.; Perez, M.; Nuria, L.; Bosch, J.; Lago, E.; Molins, E. Org. Lett. 2001, 3, 611.
22. Chutian, S.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. Enders, D.; Thiebes, C. Pure Appl. Chem. 2001, 73, 573. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, E. J., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 2, p 251. Laschat, S.; Dickner, T. Synthesis 2000, 1781. Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. Amat, M.; Perez, M.; Nuria, L.; Bosch, J.; Lago, E.; Molins, E. Org. Lett. 2001, 3, 611.
23. Chutian, S.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. Enders, D.; Thiebes, C. Pure Appl. Chem. 2001, 73, 573. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, E. J., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 2, p 251. Laschat, S.; Dickner, T. Synthesis 2000, 1781. Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. Amat, M.; Perez, M.; Nuria, L.; Bosch, J.; Lago, E.; Molins, E. Org. Lett. 2001, 3, 611.
24. Chutian, S.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. Enders, D.; Thiebes, C. Pure Appl. Chem. 2001, 73, 573. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, E. J., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 2, p 251. Laschat, S.; Dickner, T. Synthesis 2000, 1781. Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. Amat, M.; Perez, M.; Nuria, L.; Bosch, J.; Lago, E.; Molins, E. Org. Lett. 2001, 3, 611.
25. Chutian, S.; Alcudia, A.; Yin, J.; Liebeskind, L. S. J. Am. Chem. Soc. 2001, 123, 12477. Enders, D.; Thiebes, C. Pure Appl. Chem. 2001, 73, 573. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, E. J., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 2, p 251. Laschat, S.; Dickner, T. Synthesis 2000, 1781. Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. Amat, M.; Perez, M.; Nuria, L.; Bosch, J.; Lago, E.; Molins, E. Org. Lett. 2001, 3, 611.
26. Ojima, I.; Lula, D. M. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: New York, 1999; Vol. 13, pp 371-412.
27. Jefford, C. W. Curr. Org. Chem. 2000, 4, 205.
28. Broggini, G.; Zecchi, G. Synthesis 1999, 905.
29. Kibayashi, C.; Aoyagi, S. Synlett 1995, 873.
30. Husson, H.-P.; Royer, J. Chem. Soc. Rev. 1999, 28, 383.
31. Pandit, U. K.; Overkleeft, H. S.; Borer, B. C.; Bieraugel, H. Eur. J. Org. Chem. 1999, 959.
32. Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 95, 1677.
33. Comins, D. L.; Killpack, M. O. J. Am. Chem. Soc. 1992, 114, 10973. Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719.
34. Comins, D. L.; Killpack, M. O. J. Am. Chem. Soc. 1992, 114, 10973. Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719.
35. Grieco, P. A.; Larsen, S. D. J. Am. Chem. Soc. 1985, 107, 1768. Waldmann, H.; Braun, M. J. Org. Chem. 1992, 57, 4444. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520.
36. Grieco, P. A.; Larsen, S. D. J. Am. Chem. Soc. 1985, 107, 1768. Waldmann, H.; Braun, M. J. Org. Chem. 1992, 57, 4444. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520.
37. Grieco, P. A.; Larsen, S. D. J. Am. Chem. Soc. 1985, 107, 1768. Waldmann, H.; Braun, M. J. Org. Chem. 1992, 57, 4444. Ishihara, K.; Miyata, M.; Hattori, K.; Tada, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 10520.
38. Flann, C.; Malone, T. C.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6097. Tietze, L. F.; Bratz, M. Chem. Ber. 1989, 122, 997. Overman, L. E.; Sarkar, A. K. Tetrahedron Lett. 1992, 33, 4103. Laschat, S.; Fröhlich, R.; Wibbeling, B. J. Org. Chem. 1996, 61, 2829.
39. Flann, C.; Malone, T. C.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6097. Tietze, L. F.; Bratz, M. Chem. Ber. 1989, 122, 997. Overman, L. E.; Sarkar, A. K. Tetrahedron Lett. 1992, 33, 4103. Laschat, S.; Fröhlich, R.; Wibbeling, B. J. Org. Chem. 1996, 61, 2829.
40. Flann, C.; Malone, T. C.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6097. Tietze, L. F.; Bratz, M. Chem. Ber. 1989, 122, 997. Overman, L. E.; Sarkar, A. K. Tetrahedron Lett. 1992, 33, 4103. Laschat, S.; Fröhlich, R.; Wibbeling, B. J. Org. Chem. 1996, 61, 2829.
41. Flann, C.; Malone, T. C.; Overman, L. E. J. Am. Chem. Soc. 1987, 109, 6097. Tietze, L. F.; Bratz, M. Chem. Ber. 1989, 122, 997. Overman, L. E.; Sarkar, A. K. Tetrahedron Lett. 1992, 33, 4103. Laschat, S.; Fröhlich, R.; Wibbeling, B. J. Org. Chem. 1996, 61, 2829.
42. Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H. P. J. Am. Chem. Soc. 1983, 105, 7754. Amat, M.; Llor, N.; Bosch, J. Tetrahedron Lett. 1994, 35, 2223. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. Francois, D.; Lallemand, M. C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H. P. Angew. Chem., Int. Ed. 1998, 37, 104.
43. Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H. P. J. Am. Chem. Soc. 1983, 105, 7754. Amat, M.; Llor, N.; Bosch, J. Tetrahedron Lett. 1994, 35, 2223. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. Francois, D.; Lallemand, M. C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H. P. Angew. Chem., Int. Ed. 1998, 37, 104.
44. Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H. P. J. Am. Chem. Soc. 1983, 105, 7754. Amat, M.; Llor, N.; Bosch, J. Tetrahedron Lett. 1994, 35, 2223. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. Francois, D.; Lallemand, M. C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H. P. Angew. Chem., Int. Ed. 1998, 37, 104.
45. Guerrier, L.; Royer, J.; Grierson, D. S.; Husson, H. P. J. Am. Chem. Soc. 1983, 105, 7754. Amat, M.; Llor, N.; Bosch, J. Tetrahedron Lett. 1994, 35, 2223. Munchhof, M. J.; Meyers, A. I. J. Am. Chem. Soc. 1995, 117, 5399. Francois, D.; Lallemand, M. C.; Selkti, M.; Tomas, A.; Kunesch, N.; Husson, H. P. Angew. Chem., Int. Ed. 1998, 37, 104.
46. Michael, J. P. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 2001; Vol. 55, pp 91-258. Micheal, J. P. Nat. Prod. Rep. 2000, 17, 579. Daly, J. W. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1998; Vol. 50, pp 141-171. Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1993; Vol. 43, pp 185-288.
47. Michael, J. P. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 2001; Vol. 55, pp 91-258. Micheal, J. P. Nat. Prod. Rep. 2000, 17, 579. Daly, J. W. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1998; Vol. 50, pp 141-171. Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1993; Vol. 43, pp 185-288.
48. Michael, J. P. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 2001; Vol. 55, pp 91-258. Micheal, J. P. Nat. Prod. Rep. 2000, 17, 579. Daly, J. W. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1998; Vol. 50, pp 141-171. Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1993; Vol. 43, pp 185-288.
49. Michael, J. P. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 2001; Vol. 55, pp 91-258. Micheal, J. P. Nat. Prod. Rep. 2000, 17, 579. Daly, J. W. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1998; Vol. 50, pp 141-171. Daly, J. W.; Garraffo, H. M.; Spande, T. F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, CA, 1993; Vol. 43, pp 185-288.
50. Tokuyama, T.; Nishimori, N.; Karle, I. L.; Edwards, M. W.; Daly, J. W. Tetrahedron 1986, 42, 3453.
51. Aronstam, R. S.; Daly, J. W.; Spande, T. F.; Narayanan, T. K.; Albuquerque, E. X. Neurochem. Res. 1986, 11, 1227.
52. Daley, J. W. Fortschr. Chem. Org. Naturst. 1982, 41, 205.
53. For some syntheses of indolizidine 167B, see: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688. Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119. Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797. Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445. Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151. Angle, S. R.; Henry, R. M. J. Org. Chem. 1997, 62, 8549. Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J. C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661. Chênevert, R.; Ziarani, G. M.; Dasser, M. Heterocycles 1999, 51, 593.
54. For some syntheses of indolizidine 167B, see: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688. Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119. Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797. Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445. Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151. Angle, S. R.; Henry, R. M. J. Org. Chem. 1997, 62, 8549. Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J. C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661. Chênevert, R.; Ziarani, G. M.; Dasser, M. Heterocycles 1999, 51, 593.
55. For some syntheses of indolizidine 167B, see: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688. Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119. Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797. Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445. Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151. Angle, S. R.; Henry, R. M. J. Org. Chem. 1997, 62, 8549. Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J. C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661. Chênevert, R.; Ziarani, G. M.; Dasser, M. Heterocycles 1999, 51, 593.
56. For some syntheses of indolizidine 167B, see: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688. Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119. Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797. Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445. Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151. Angle, S. R.; Henry, R. M. J. Org. Chem. 1997, 62, 8549. Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J. C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661. Chênevert, R.; Ziarani, G. M.; Dasser, M. Heterocycles 1999, 51, 593.
57. For some syntheses of indolizidine 167B, see: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688. Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119. Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797. Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445. Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151. Angle, S. R.; Henry, R. M. J. Org. Chem. 1997, 62, 8549. Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J. C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661. Chênevert, R.; Ziarani, G. M.; Dasser, M. Heterocycles 1999, 51, 593.
58. For some syntheses of indolizidine 167B, see: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688. Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119. Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797. Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445. Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151. Angle, S. R.; Henry, R. M. J. Org. Chem. 1997, 62, 8549. Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J. C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661. Chênevert, R.; Ziarani, G. M.; Dasser, M. Heterocycles 1999, 51, 593.
59. For some syntheses of indolizidine 167B, see: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688. Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119. Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797. Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445. Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151. Angle, S. R.; Henry, R. M. J. Org. Chem. 1997, 62, 8549. Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J. C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661. Chênevert, R.; Ziarani, G. M.; Dasser, M. Heterocycles 1999, 51, 593.
60. For some syntheses of indolizidine 167B, see: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688. Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119. Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797. Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445. Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151. Angle, S. R.; Henry, R. M. J. Org. Chem. 1997, 62, 8549. Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J. C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661. Chênevert, R.; Ziarani, G. M.; Dasser, M. Heterocycles 1999, 51, 593.
61. For some syntheses of indolizidine 167B, see: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688. Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119. Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797. Lee, E.; Li, K. S.; Lim, J. Tetrahedron Lett. 1996, 37, 1445. Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151. Angle, S. R.; Henry, R. M. J. Org. Chem. 1997, 62, 8549. Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J. C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661. Chênevert, R.; Ziarani, G. M.; Dasser, M. Heterocycles 1999, 51, 593.
62. For some syntheses of indolizidine 209D, see: Ahman, J.; Somfai, P. Tetrahedron Lett. 1995, 51, 303. Ahman, J.; Somfai, P. Tetrahedron 1995, 51, 9747. Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. Jefford, C. W.; Sienkiewicz, K.; Thornton, S. R. Helv. Chim. Acta 1995, 78, 1511. Takahata, H.; Kubota, M.; Ihara, K.; Okamoto, N.; Momose, T.; Azer, N.; Eldefrawi, A. T.; Eldefrawi, M. E. Tetrahedron: Asymmetry 1998, 9, 3289. Chênevert, R.; Ziarani, G. M.; Morin, M. P.; Dasser, M. Tetrahedron: Asymmetry 1999, 10, 3117. Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465. Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543.
63. For some syntheses of indolizidine 209D, see: Ahman, J.; Somfai, P. Tetrahedron Lett. 1995, 51, 303. Ahman, J.; Somfai, P. Tetrahedron 1995, 51, 9747. Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. Jefford, C. W.; Sienkiewicz, K.; Thornton, S. R. Helv. Chim. Acta 1995, 78, 1511. Takahata, H.; Kubota, M.; Ihara, K.; Okamoto, N.; Momose, T.; Azer, N.; Eldefrawi, A. T.; Eldefrawi, M. E. Tetrahedron: Asymmetry 1998, 9, 3289. Chênevert, R.; Ziarani, G. M.; Morin, M. P.; Dasser, M. Tetrahedron: Asymmetry 1999, 10, 3117. Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465. Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543.
64. For some syntheses of indolizidine 209D, see: Ahman, J.; Somfai, P. Tetrahedron Lett. 1995, 51, 303. Ahman, J.; Somfai, P. Tetrahedron 1995, 51, 9747. Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. Jefford, C. W.; Sienkiewicz, K.; Thornton, S. R. Helv. Chim. Acta 1995, 78, 1511. Takahata, H.; Kubota, M.; Ihara, K.; Okamoto, N.; Momose, T.; Azer, N.; Eldefrawi, A. T.; Eldefrawi, M. E. Tetrahedron: Asymmetry 1998, 9, 3289. Chênevert, R.; Ziarani, G. M.; Morin, M. P.; Dasser, M. Tetrahedron: Asymmetry 1999, 10, 3117. Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465. Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543.
65. For some syntheses of indolizidine 209D, see: Ahman, J.; Somfai, P. Tetrahedron Lett. 1995, 51, 303. Ahman, J.; Somfai, P. Tetrahedron 1995, 51, 9747. Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. Jefford, C. W.; Sienkiewicz, K.; Thornton, S. R. Helv. Chim. Acta 1995, 78, 1511. Takahata, H.; Kubota, M.; Ihara, K.; Okamoto, N.; Momose, T.; Azer, N.; Eldefrawi, A. T.; Eldefrawi, M. E. Tetrahedron: Asymmetry 1998, 9, 3289. Chênevert, R.; Ziarani, G. M.; Morin, M. P.; Dasser, M. Tetrahedron: Asymmetry 1999, 10, 3117. Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465. Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543.
66. For some syntheses of indolizidine 209D, see: Ahman, J.; Somfai, P. Tetrahedron Lett. 1995, 51, 303. Ahman, J.; Somfai, P. Tetrahedron 1995, 51, 9747. Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. Jefford, C. W.; Sienkiewicz, K.; Thornton, S. R. Helv. Chim. Acta 1995, 78, 1511. Takahata, H.; Kubota, M.; Ihara, K.; Okamoto, N.; Momose, T.; Azer, N.; Eldefrawi, A. T.; Eldefrawi, M. E. Tetrahedron: Asymmetry 1998, 9, 3289. Chênevert, R.; Ziarani, G. M.; Morin, M. P.; Dasser, M. Tetrahedron: Asymmetry 1999, 10, 3117. Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465. Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543.
67. For some syntheses of indolizidine 209D, see: Ahman, J.; Somfai, P. Tetrahedron Lett. 1995, 51, 303. Ahman, J.; Somfai, P. Tetrahedron 1995, 51, 9747. Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. Jefford, C. W.; Sienkiewicz, K.; Thornton, S. R. Helv. Chim. Acta 1995, 78, 1511. Takahata, H.; Kubota, M.; Ihara, K.; Okamoto, N.; Momose, T.; Azer, N.; Eldefrawi, A. T.; Eldefrawi, M. E. Tetrahedron: Asymmetry 1998, 9, 3289. Chênevert, R.; Ziarani, G. M.; Morin, M. P.; Dasser, M. Tetrahedron: Asymmetry 1999, 10, 3117. Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465. Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543.
68. For some syntheses of indolizidine 209D, see: Ahman, J.; Somfai, P. Tetrahedron Lett. 1995, 51, 303. Ahman, J.; Somfai, P. Tetrahedron 1995, 51, 9747. Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. Jefford, C. W.; Sienkiewicz, K.; Thornton, S. R. Helv. Chim. Acta 1995, 78, 1511. Takahata, H.; Kubota, M.; Ihara, K.; Okamoto, N.; Momose, T.; Azer, N.; Eldefrawi, A. T.; Eldefrawi, M. E. Tetrahedron: Asymmetry 1998, 9, 3289. Chênevert, R.; Ziarani, G. M.; Morin, M. P.; Dasser, M. Tetrahedron: Asymmetry 1999, 10, 3117. Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465. Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543.
69. For some syntheses of indolizidine 209D, see: Ahman, J.; Somfai, P. Tetrahedron Lett. 1995, 51, 303. Ahman, J.; Somfai, P. Tetrahedron 1995, 51, 9747. Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398. Jefford, C. W.; Sienkiewicz, K.; Thornton, S. R. Helv. Chim. Acta 1995, 78, 1511. Takahata, H.; Kubota, M.; Ihara, K.; Okamoto, N.; Momose, T.; Azer, N.; Eldefrawi, A. T.; Eldefrawi, M. E. Tetrahedron: Asymmetry 1998, 9, 3289. Chênevert, R.; Ziarani, G. M.; Morin, M. P.; Dasser, M. Tetrahedron: Asymmetry 1999, 10, 3117. Yamazaki, N.; Ito, T.; Kibayashi, C. Org. Lett. 2000, 2, 465. Back, T. G.; Nakajima, K. J. Org. Chem. 2000, 65, 4543.
70. Garraffo, H. M.; Jain, P.; Spande, T. F.; Daly, J. W. J. Nat. Prod. 1997, 60, 2.
71. Toyooka, N.; Fukutome, A.; Nemoto, H.; Daly, J. W.; Spande, T. F.; Garraffo, H. M.; Kaneko, T. Org. Lett. 2002, 4, 1715.
72. Momose, T.; Toyooka, N. J. Org. Chem. 1994, 59, 943. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron 1997, 53, 9553.
73. Momose, T.; Toyooka, N. J. Org. Chem. 1994, 59, 943. Toyooka, N.; Tanaka, K.; Momose, T.; Daly, J. W.; Garraffo, H. M. Tetrahedron 1997, 53, 9553.
74. For an excellent review of the subject, see: Ciufolini, M. A.; Hermann, C. Y. W.; Dong, Q.; Shimiizu, T.; Swaminathan, S.; Xi, N. Synlett. 1998, 105.
75. Haukaas, M. H.; O'Doherty, G. A. Org. Lett. 2001, 3, 401.
76. For a preliminary report, see: Harris, J. M.; Padwa, A. Org. Lett. 2002, 4, 2029.
77. Yang, C. F.; Xu, Y. M.; Liao, L. X.; Zhou, W. S. Tetrahedron Lett. 1998, 39, 9227.
78. Altenbach, H. J.; Wischnat, R. Tetrahedron Lett. 1995, 36, 4983.
79. Zhou, W. S.; Lu, Z. H.; Xu, Y. M.; Liao, L. X.; Wang, Z. M. Tetrahedron 1999, 55, 11959. Zhou, W. S.; Xie, W. G.; Lu, Z. H.; Pan, X. F. J. Chem. Soc., Perkin Trans. 1 1995, 2599.
80. Zhou, W. S.; Lu, Z. H.; Xu, Y. M.; Liao, L. X.; Wang, Z. M. Tetrahedron 1999, 55, 11959. Zhou, W. S.; Xie, W. G.; Lu, Z. H.; Pan, X. F. J. Chem. Soc., Perkin Trans. 1 1995, 2599.
81. Lu, Z. H.; Zhou, W. S. J. Chem. Soc., Perkin Trans. 1 1993, 593. Zhou, W. S.; Xie, W. G.; Lu, Z. H.; Pan, X. F. Tetrahedron Lett. 1995, 36, 1291.
82. Lu, Z. H.; Zhou, W. S. J. Chem. Soc., Perkin Trans. 1 1993, 593. Zhou, W. S.; Xie, W. G.; Lu, Z. H.; Pan, X. F. Tetrahedron Lett. 1995, 36, 1291.
83. Koulocheri, S. D.; Magiatis, P.; Skaltsounis, A. L.; Haroutounian, S. A. Tetrahedron 2000, 56, 6135.
84. Liao, L. X.; Wang, Z. M.; Shang, Z. X.; Zhou, W. S. Tetrahedron: Asymmetry 1999, 10, 3649.
85. For some related 1,4-additions, see ref 34.
86. The 2-axial conformation of N-acylpiperidines is well established. See: Brown, J. D.; Foley, M. A.; Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445.
87. Apostolopoulos, C. D.; Couladouros, E. A.; Georgiadis, M. P. Liebigs Ann. Chem. 1994, 781. Couladouros, E. A.; Apostolopoulos, C. D.; Georgiadis, M. P. Carbohydr. Res. 1993, 249, 399.
88. Apostolopoulos, C. D.; Couladouros, E. A.; Georgiadis, M. P. Liebigs Ann. Chem. 1994, 781. Couladouros, E. A.; Apostolopoulos, C. D.; Georgiadis, M. P. Carbohydr. Res. 1993, 249, 399.
89. Shono, T.; Matsumara, Y.; Tsubata, K.; Uchida, K. J. Org. Chem. 1986, 51, 2590.
90. Hopman, J. C. P.; van de Berg, E.; Ollero, L. O.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1995, 36, 4315.
91. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413.
92. For several examples of the synthesis of piperidines via olefin metathesis, see: Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324. Huwe, C. M.; Kiehl, O. C.; Blechert, S. Synlett. 1996, 65. Rutjes, F. P. J. T.; Schoemaker, H. E. Tetrahedron Lett. 1997, 38, 677. Jo, E.; Na, Y.; Chang, S. Tetrahedron Lett. 1999, 40, 5581.
93. For several examples of the synthesis of piperidines via olefin metathesis, see: Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324. Huwe, C. M.; Kiehl, O. C.; Blechert, S. Synlett. 1996, 65. Rutjes, F. P. J. T.; Schoemaker, H. E. Tetrahedron Lett. 1997, 38, 677. Jo, E.; Na, Y.; Chang, S. Tetrahedron Lett. 1999, 40, 5581.
94. For several examples of the synthesis of piperidines via olefin metathesis, see: Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324. Huwe, C. M.; Kiehl, O. C.; Blechert, S. Synlett. 1996, 65. Rutjes, F. P. J. T.; Schoemaker, H. E. Tetrahedron Lett. 1997, 38, 677. Jo, E.; Na, Y.; Chang, S. Tetrahedron Lett. 1999, 40, 5581.
95. For several examples of the synthesis of piperidines via olefin metathesis, see: Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324. Huwe, C. M.; Kiehl, O. C.; Blechert, S. Synlett. 1996, 65. Rutjes, F. P. J. T.; Schoemaker, H. E. Tetrahedron Lett. 1997, 38, 677. Jo, E.; Na, Y.; Chang, S. Tetrahedron Lett. 1999, 40, 5581.
96. 2 and allyl silane instead of converting it to the corresponding methoxy derivative as had been done with the related hemiaminal 13.
97. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979.
98. Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
99. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis; Wiley: New York, 1991; pp 379-381.
100. Ji, S.; Gortler, L. B.; Waring, A.; Battisti, A.; Bank, S.; Closson, W. D.; Wriede, P. J. Am. Chem. Soc. 1967, 89, 5311.
101. We wish to thank Professor Naoki Toyooka for providing us with photocopies of the proton and carbon NMR spectra of synthetic epi (5a) and revised (5b) indolizidine alkaloids 223A.
102. Trost, B. M.; Marrs, C. J. Org. Chem. 1991, 56, 6468.
103. Zhou, W. S.; Lu, Z. H.; Wang, Z. M. Tetrahedron 1993, 49, 2641.
104. Popandova-Yambolieva, K. Synth. Commun. 1990, 20, 1857.