A new approach to the construction of pyrrolizidine and indolizidine skeleton: Enantioselective synthesis of (1S, 7aS)-1-hydroxypyrrolizidine and (1S, 8aS)-1-hydroxyindolizidine

Chinese Chemical Letters

Volumn 8, Issue 9, 1997, Pages 773-776

  Dong, Han Qing ^a   Shi, Zhi Cai ^a   Lin, Guo Qiang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031479313     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

1. Herczcgh, P.; Koracs, I. and Szatricskai., Recent Progress in the Synthesis of Antibiotics and Related Microbial Products. Vol. 2. Lukacs. G. (Ed.); Springer-Verlag. N.Y. 1993: pp451.
2. Some selected reports on the recent syntheses of pyrrolizidine and indolizidine alkaloids: (a) Shono, T.; Kise, N. and Tanabe, T., J. Org. Chem. 1988, 53, 1364. (b) Dener, J.M.; Hart, D.J. and Ramesh, S., J. Org. Chem. 1988, 53, 6022. (c) Dener, J.M. and Hart, D.J., Tetrahedron 1988. 44, 7037. (d) Jolly, R.S. and Livinghouse. T., J Am. Chem. Soc. 1988. 110, 7536. (e) Heidl, P.C.; Bergmeier, S.C. and Pearson, W.H., Tetrahedron Lett. 1990, 31, 5441. (f) McCaig, A.E. and Wightman, R.H., Tetrahedron Lett. 1993, 34, 3939. (g) Mulzer, J. and Scharp, M., Synthesis 1993, 615. (h) Murray, A.; Proctor, G.R. and Murray, P.J., Tetrahedron Lett. 1995, 36, 291. (i) Murray, A.; Proctor. G.R. and Murray, P.J., Tetrahedron 1996, 52, 3757.
3. Some selected reports on the recent syntheses of pyrrolizidine and indolizidine alkaloids: (a) Shono, T.; Kise, N. and Tanabe, T., J. Org. Chem. 1988, 53, 1364. (b) Dener, J.M.; Hart, D.J. and Ramesh, S., J. Org. Chem. 1988, 53, 6022. (c) Dener, J.M. and Hart, D.J., Tetrahedron 1988. 44, 7037. (d) Jolly, R.S. and Livinghouse. T., J Am. Chem. Soc. 1988. 110, 7536. (e) Heidl, P.C.; Bergmeier, S.C. and Pearson, W.H., Tetrahedron Lett. 1990, 31, 5441. (f) McCaig, A.E. and Wightman, R.H., Tetrahedron Lett. 1993, 34, 3939. (g) Mulzer, J. and Scharp, M., Synthesis 1993, 615. (h) Murray, A.; Proctor, G.R. and Murray, P.J., Tetrahedron Lett. 1995, 36, 291. (i) Murray, A.; Proctor. G.R. and Murray, P.J., Tetrahedron 1996, 52, 3757.
4. Some selected reports on the recent syntheses of pyrrolizidine and indolizidine alkaloids: (a) Shono, T.; Kise, N. and Tanabe, T., J. Org. Chem. 1988, 53, 1364. (b) Dener, J.M.; Hart, D.J. and Ramesh, S., J. Org. Chem. 1988, 53, 6022. (c) Dener, J.M. and Hart, D.J., Tetrahedron 1988. 44, 7037. (d) Jolly, R.S. and Livinghouse. T., J Am. Chem. Soc. 1988. 110, 7536. (e) Heidl, P.C.; Bergmeier, S.C. and Pearson, W.H., Tetrahedron Lett. 1990, 31, 5441. (f) McCaig, A.E. and Wightman, R.H., Tetrahedron Lett. 1993, 34, 3939. (g) Mulzer, J. and Scharp, M., Synthesis 1993, 615. (h) Murray, A.; Proctor, G.R. and Murray, P.J., Tetrahedron Lett. 1995, 36, 291. (i) Murray, A.; Proctor. G.R. and Murray, P.J., Tetrahedron 1996, 52, 3757.
5. Some selected reports on the recent syntheses of pyrrolizidine and indolizidine alkaloids: (a) Shono, T.; Kise, N. and Tanabe, T., J. Org. Chem. 1988, 53, 1364. (b) Dener, J.M.; Hart, D.J. and Ramesh, S., J. Org. Chem. 1988, 53, 6022. (c) Dener, J.M. and Hart, D.J., Tetrahedron 1988. 44, 7037. (d) Jolly, R.S. and Livinghouse. T., J Am. Chem. Soc. 1988. 110, 7536. (e) Heidl, P.C.; Bergmeier, S.C. and Pearson, W.H., Tetrahedron Lett. 1990, 31, 5441. (f) McCaig, A.E. and Wightman, R.H., Tetrahedron Lett. 1993, 34, 3939. (g) Mulzer, J. and Scharp, M., Synthesis 1993, 615. (h) Murray, A.; Proctor, G.R. and Murray, P.J., Tetrahedron Lett. 1995, 36, 291. (i) Murray, A.; Proctor. G.R. and Murray, P.J., Tetrahedron 1996, 52, 3757.
6. Some selected reports on the recent syntheses of pyrrolizidine and indolizidine alkaloids: (a) Shono, T.; Kise, N. and Tanabe, T., J. Org. Chem. 1988, 53, 1364. (b) Dener, J.M.; Hart, D.J. and Ramesh, S., J. Org. Chem. 1988, 53, 6022. (c) Dener, J.M. and Hart, D.J., Tetrahedron 1988. 44, 7037. (d) Jolly, R.S. and Livinghouse. T., J Am. Chem. Soc. 1988. 110, 7536. (e) Heidl, P.C.; Bergmeier, S.C. and Pearson, W.H., Tetrahedron Lett. 1990, 31, 5441. (f) McCaig, A.E. and Wightman, R.H., Tetrahedron Lett. 1993, 34, 3939. (g) Mulzer, J. and Scharp, M., Synthesis 1993, 615. (h) Murray, A.; Proctor, G.R. and Murray, P.J., Tetrahedron Lett. 1995, 36, 291. (i) Murray, A.; Proctor. G.R. and Murray, P.J., Tetrahedron 1996, 52, 3757.
7. Some selected reports on the recent syntheses of pyrrolizidine and indolizidine alkaloids: (a) Shono, T.; Kise, N. and Tanabe, T., J. Org. Chem. 1988, 53, 1364. (b) Dener, J.M.; Hart, D.J. and Ramesh, S., J. Org. Chem. 1988, 53, 6022. (c) Dener, J.M. and Hart, D.J., Tetrahedron 1988. 44, 7037. (d) Jolly, R.S. and Livinghouse. T., J Am. Chem. Soc. 1988. 110, 7536. (e) Heidl, P.C.; Bergmeier, S.C. and Pearson, W.H., Tetrahedron Lett. 1990, 31, 5441. (f) McCaig, A.E. and Wightman, R.H., Tetrahedron Lett. 1993, 34, 3939. (g) Mulzer, J. and Scharp, M., Synthesis 1993, 615. (h) Murray, A.; Proctor, G.R. and Murray, P.J., Tetrahedron Lett. 1995, 36, 291. (i) Murray, A.; Proctor. G.R. and Murray, P.J., Tetrahedron 1996, 52, 3757.
8. Some selected reports on the recent syntheses of pyrrolizidine and indolizidine alkaloids: (a) Shono, T.; Kise, N. and Tanabe, T., J. Org. Chem. 1988, 53, 1364. (b) Dener, J.M.; Hart, D.J. and Ramesh, S., J. Org. Chem. 1988, 53, 6022. (c) Dener, J.M. and Hart, D.J., Tetrahedron 1988. 44, 7037. (d) Jolly, R.S. and Livinghouse. T., J Am. Chem. Soc. 1988. 110, 7536. (e) Heidl, P.C.; Bergmeier, S.C. and Pearson, W.H., Tetrahedron Lett. 1990, 31, 5441. (f) McCaig, A.E. and Wightman, R.H., Tetrahedron Lett. 1993, 34, 3939. (g) Mulzer, J. and Scharp, M., Synthesis 1993, 615. (h) Murray, A.; Proctor, G.R. and Murray, P.J., Tetrahedron Lett. 1995, 36, 291. (i) Murray, A.; Proctor. G.R. and Murray, P.J., Tetrahedron 1996, 52, 3757.
9. Some selected reports on the recent syntheses of pyrrolizidine and indolizidine alkaloids: (a) Shono, T.; Kise, N. and Tanabe, T., J. Org. Chem. 1988, 53, 1364. (b) Dener, J.M.; Hart, D.J. and Ramesh, S., J. Org. Chem. 1988, 53, 6022. (c) Dener, J.M. and Hart, D.J., Tetrahedron 1988. 44, 7037. (d) Jolly, R.S. and Livinghouse. T., J Am. Chem. Soc. 1988. 110, 7536. (e) Heidl, P.C.; Bergmeier, S.C. and Pearson, W.H., Tetrahedron Lett. 1990, 31, 5441. (f) McCaig, A.E. and Wightman, R.H., Tetrahedron Lett. 1993, 34, 3939. (g) Mulzer, J. and Scharp, M., Synthesis 1993, 615. (h) Murray, A.; Proctor, G.R. and Murray, P.J., Tetrahedron Lett. 1995, 36, 291. (i) Murray, A.; Proctor. G.R. and Murray, P.J., Tetrahedron 1996, 52, 3757.
10. Some selected reports on the recent syntheses of pyrrolizidine and indolizidine alkaloids: (a) Shono, T.; Kise, N. and Tanabe, T., J. Org. Chem. 1988, 53, 1364. (b) Dener, J.M.; Hart, D.J. and Ramesh, S., J. Org. Chem. 1988, 53, 6022. (c) Dener, J.M. and Hart, D.J., Tetrahedron 1988. 44, 7037. (d) Jolly, R.S. and Livinghouse. T., J Am. Chem. Soc. 1988. 110, 7536. (e) Heidl, P.C.; Bergmeier, S.C. and Pearson, W.H., Tetrahedron Lett. 1990, 31, 5441. (f) McCaig, A.E. and Wightman, R.H., Tetrahedron Lett. 1993, 34, 3939. (g) Mulzer, J. and Scharp, M., Synthesis 1993, 615. (h) Murray, A.; Proctor, G.R. and Murray, P.J., Tetrahedron Lett. 1995, 36, 291. (i) Murray, A.; Proctor. G.R. and Murray, P.J., Tetrahedron 1996, 52, 3757.
11. Zhao, H. and Mootoo, D.R., J. Org. Chem. 1996, 61, 6762.
12. (a) CA 110: 114617b
13. [ Gundermann, H. and Schnekenburger, J., Arch. Pharm. 1988. 321(12), 925. ].
14. (b) CA 110: 57007b [ Gundermann, H.; Wolff, C. and Schnekenburger, J., ibid. 1988, 321(11), 799.]
15. (b) CA 110: 57007b [ Gundermann, H.; Wolff, C. and Schnekenburger, J., ibid. 1988, 321(11), 799.]
16. Cossy, J. and Vogel, P., In Studies in Natural Products Chemistry, vol.12; Stereoselective Synthesis (Part H): A.-ur-Rahman. Ed.; Elsevier. 1993; pp275. and references cited therein.
17. (a) Häfele, B.; Schröler, D. and Jäger, V., Angew. Chem. Int. Ed. Engl. 1986, 25, 87.
18. (b) Jäger V.; Hümmer, W.; Stahl, U. and Gracza, T., Synthesis 1991, 769.
19. (c) Hatakeyama, S.; Sakurai, K. and Takano, S., J Chem. Soc. Chem. Commun. 1985, 1759.
20. (d) Schreiber,S. L.; Schreiber, T.S. and Smith, D.B., J. Am. Chem. Soc. 1987, 109, 1525.
21. (e) Atsuumi, S.; Nakano, M.; Koike, Y.; Tanaka, S.; Funabashi, H.; Hashimoto, J. and Morishima, H., Chem. Pharm. Bull. 1990, 38, 3460.
22. (a) Shi, Z. C. and Lin, G.Q., Tetrahedron: Asymmetry 1995, 6, 2907.
23. (b) Shi, Z. C.; Zeng, C. M. and Lin, G.Q., Heterocycles 1995, 41, 277.
24. Hansen, A.; Tagmose, T. M. and Bols. M., Tetrahedron 1997, 53, 697.
25. Aaron, H. S.; Rader, C. P. and Wicks, Jr.G.E., J. Org. Chem. 1966, 31, 3502.
26. Naruse, M.; Aoyagi, S. and Kibayashi, C., J. Org. Chem. 1994, 59, 1358.
27. Rao, V. S. and Perlin, A. S., Carbohydrate Research 1980, 83, 175.