Synthesis of (±)-Indolizidine 209B and a New 209B Diastereoisomer

Synlett

Volumn 1996, Issue 10, 1996, Pages 981-982

  Michael, Joseph P ^a   Gravestock, David ^a  

^a UNIVERSITY OF THE WITWATERSRAND   (South Africa)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001669890     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5646     Document Type: Article

References (25)

1. Daly, J. W.; Garraffo, H. M.; Spande, T. F. Alkaloids (N.Y.) 1993, 43, 185.
2. Daly, J. W.; Myers, C. W.; Whittaker, N. Toxicon 1987, 25, 1023.
3. Daly, J. W.; Nishizawa, Y.; Padgett, W. L.; Tokuyama, T.; Smith, A. L.; Holmes, A. B.; Kibayashi, C.; Aronstam, R. S. Neurochem. Res. 1991, 16, 1213.
4. Holmes, A. B.; Smith, A. L.; Williams, S. F.; Hughes, L. R.; Lidert, Z.; Swithenbank, C. J. Org. Chem. 1991, 56, 1393.
5. Gnecco, D.; Marazano, C.; Das, B. C. J. Chem. Soc., Chem. Commun. 1991, 625.
6. Jefford, C. W.; Sienkiewicz, K.; Thoraton, S. R. Helv. Chim. Acta 1995, 78, 1511.
7. For other syntheses of (-)-indolizidine 209B, see: Shishido, Y.; Kibayashi, C. J. Org. Chem. 1992, 57, 2876. Satake, A.; Shimizu, I. Tetrahedron: Asymmetry 1993, 4, 1405. Momose, T.; Toyooka, N. J. Org. Chem. 1993, 59, 943. Aubé, J.; Rafferty, P. S.; Milligan, G. L. Heterocycles 1993, 35, 1141. Åhman, J.; Somfai, P. Tetrahedron 1995, 51, 9747.
8. For other syntheses of (-)-indolizidine 209B, see: Shishido, Y.; Kibayashi, C. J. Org. Chem. 1992, 57, 2876. Satake, A.; Shimizu, I. Tetrahedron: Asymmetry 1993, 4, 1405. Momose, T.; Toyooka, N. J. Org. Chem. 1993, 59, 943. Aubé, J.; Rafferty, P. S.; Milligan, G. L. Heterocycles 1993, 35, 1141. Åhman, J.; Somfai, P. Tetrahedron 1995, 51, 9747.
9. For other syntheses of (-)-indolizidine 209B, see: Shishido, Y.; Kibayashi, C. J. Org. Chem. 1992, 57, 2876. Satake, A.; Shimizu, I. Tetrahedron: Asymmetry 1993, 4, 1405. Momose, T.; Toyooka, N. J. Org. Chem. 1993, 59, 943. Aubé, J.; Rafferty, P. S.; Milligan, G. L. Heterocycles 1993, 35, 1141. Åhman, J.; Somfai, P. Tetrahedron 1995, 51, 9747.
10. For other syntheses of (-)-indolizidine 209B, see: Shishido, Y.; Kibayashi, C. J. Org. Chem. 1992, 57, 2876. Satake, A.; Shimizu, I. Tetrahedron: Asymmetry 1993, 4, 1405. Momose, T.; Toyooka, N. J. Org. Chem. 1993, 59, 943. Aubé, J.; Rafferty, P. S.; Milligan, G. L. Heterocycles 1993, 35, 1141. Åhman, J.; Somfai, P. Tetrahedron 1995, 51, 9747.
11. For other syntheses of (-)-indolizidine 209B, see: Shishido, Y.; Kibayashi, C. J. Org. Chem. 1992, 57, 2876. Satake, A.; Shimizu, I. Tetrahedron: Asymmetry 1993, 4, 1405. Momose, T.; Toyooka, N. J. Org. Chem. 1993, 59, 943. Aubé, J.; Rafferty, P. S.; Milligan, G. L. Heterocycles 1993, 35, 1141. Åhman, J.; Somfai, P. Tetrahedron 1995, 51, 9747.
12. Comins, D. L.; Zeller, E. Tetrahedron Lett. 1991, 32, 5889.
13. Michael, J. P.; Jungmann, C. M. Tetrahedron 1992, 48, 10211. Michael, J. P.; Parsons, A. S. Tetrahedron 1996, 52, 2199. Other examples of our approach to alkaloid synthesis may be found in the references cited in these two articles.
14. Michael, J. P.; Jungmann, C. M. Tetrahedron 1992, 48, 10211. Michael, J. P.; Parsons, A. S. Tetrahedron 1996, 52, 2199. Other examples of our approach to alkaloid synthesis may be found in the references cited in these two articles.
15. 13C NMR and IR spectroscopies, and either HRMS (liquids) or microanarysis (solids).
16. Roth, M.; Dubs, P.; Götschi, E.; Eschenmoser, A. Helv. Chim. Acta 1971, 54, 710. Shiosaki, K. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; pp. 865-892.
17. Roth, M.; Dubs, P.; Götschi, E.; Eschenmoser, A. Helv. Chim. Acta 1971, 54, 710. Shiosaki, K. In Comprehensive Organic Synthesis, Vol. 2; Trost, B. M., Ed.; Pergamon Press: Oxford, 1991; pp. 865-892.
18. Stevens, R. V. Acc. Chem. Res. 1984, 17, 289.
19. 2 requires 267.2198.
20. 27N requires 209.2144.
21. Dr C. Marazano, CNRS, Gif-sur-Yvette, personal communication. We are grateful to Dr Marazano for this information, and for supplying us with spectroscopic data for compounds 1 and 15.
22. Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1991, 56, 4868.
23. Garraffo, H. M.; Spande, T. F.; Daly, J. W.; Baldessari, A.; Gros, E. G. J. Nat. Prod. 1993, 56, 357. Garraffo, H. M.; Caceres, J.; Daly, J. W.; Spande, T. F.; Andriamaharavo, N. R.; Andriantsiferana, M. J. Nat. Prod. 1993, 56, 1016.
24. Garraffo, H. M.; Spande, T. F.; Daly, J. W.; Baldessari, A.; Gros, E. G. J. Nat. Prod. 1993, 56, 357. Garraffo, H. M.; Caceres, J.; Daly, J. W.; Spande, T. F.; Andriamaharavo, N. R.; Andriantsiferana, M. J. Nat. Prod. 1993, 56, 1016.
25. Michael, J. P.; Gravestock, D. Pure Appl. Chem. In press.