Anionic cyclizations of chiral 2,3-dihydro-4-pyridones: A five-step, asymmetric synthesis of indolizidine 209D

Journal of the American Chemical Society

Volumn 118, Issue 48, 1996, Pages 12248-12249

  Comins, Daniel L ^a   Zhang, Yue Mei ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; INDOLIZIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030458106     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9626446     Document Type: Article

References (17)

1. (a) Comins, D. L.; Guerra-Weltzien, L. Tetrahedron Lett. 1996, 37. 3807 and references cited therein.
2. (b) Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, C. J., Ed.; JAI Press, Inc.: Greenwich, CT, 1996; Vol. 2, pp 251-294.
3. Comins, D. L.; Joseph, S. P.; Zhang, Y. Tetrahedron Lett. 1996, 37, 793.
4. For a review on anionic cyclizations, see: Thebtaranonth, C.; Thebtaranonth, Y. Cyclization Reactions; CRC Press, Inc.: London, 1994; Chapter 4, pp 169-242.
5. (a) For a review on the chemistry of enaminones, see: Greenhill, J. V. Chem. Soc. Rev. 1977, 6, 277-294.
6. (b) Shawe, T. T.; Landino, L. M.; Ross, A. A.; Prokopowicz, A. S.; Robinson, P. M.; Cannon, A. Tetrahedron Lett. 1996, 37, 3823 and references cited therein.
7. Beckwith, A. L. J.; Joseph, S. P.; Mayadunne, T. A. J. Org. Chem. 1993, 58, 4198.
8. (a) 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.
9. (b) For an asymmetric synthesis of indolizidine 209D, see: Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688.
10. Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719.
11. Comins, D. L.; Guerra-Weltzicn, L.; Salvador, J. M. Synlett 1994, 972.
12. Al-awar, R. S.; Joseph, S. P.; Comins, D. L. J. Org. Chem. 1993, 58, 7732.
13. (a) Meyer, C; Marek, I.; Normant, J.-F. Synlett 1993, 386.
14. (b) Sato, Y.; Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron 1994, 50. 371.
15. Comins, D. L.; Dehghani, A. Tetrahedron Lett. 1992, 33, 6299.
16. 6b See table of spectral data in the Supporting Information.
17. All new compounds were spectroscopically characterized and furnished satisfactory elemental analyses (C, H, N ±0.4%) or high-resolution mass spectra. Details are provided in the Supporting Information.