Asymmetric synthesis of (-)-indolizidines 167B and 209D based on stereocontrolled allylation of a chiral tricyclic N-acyl-N,O-acetal

Organic Letters

Volumn 2, Issue 4, 2000, Pages 465-466

  Yamazaki, Naoki ^a   Ito, Toshimasa ^a   Kibayashi, Chihiro ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; INDOLE DERIVATIVE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ACETALS; INDOLES; STEREOISOMERISM;

EID: 0034707982     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990389z     Document Type: Article

References (24)

1. For a recent review, see: Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503.
2. (a) Burgess, L. E.; Meyers, A. I. J. Am. Chem. Soc. 1991, 113, 9858.
3. (b) Meyers, A. I.; Burgess, L. E. J. Org. Chem. 1991, 56, 2294.
4. Amat, M.; Llor, N.; Bosch, J. Tetrahedron Lett. 1994, 35, 2223.
5. (a) Yamazaki, N.; Ito, T.; Kibayashi, C. Synlett 1999, 37.
6. (b) Yamazaki, N.; Ito, T.; Kibayashi, C. Tetrahedron Lett. 1999, 40, 739.
7. For enantioselective syntheses of indolizidine 167B, see: (a) Polniaszek, R. P.; Belmont, S. E. J. Org. Chem. 1990, 55, 4688.
8. (b) Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513.
9. (c) Fleurant, A.; Célérier, J. P.; Lhommet, G. Tetrahedron: Asymmetry 1992, 3, 695.
10. (d) Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119.
11. (e) Fleurant, A.; Saliou, C.; Célérier, J. P.; Platzer, N.; Moc, T. V.; Lhommet, G. J. Heterocycl. Chem. 1995, 32, 255.
12. (f) Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1995, 41, 1797.
13. (g) Lee, E.; Li, K. S. Lim, J. Tetrahedron Lett. 1996, 37, 1445.
14. (h) Weymann, M.; Pfrengle, W.; Schollmeyer, D.; Kunz, H. Synthesis 1997, 1151.
15. (i) Angle, S. R.; Henry, R. M. J. Org. Chem. 1997, 62, 8549.
16. (j) Chalard, P.; Remuson, R.; Gelas-Mialhe, Y.; Gramain, J.-C.; Canet, I. Tetrahedron Lett. 1999, 40, 1661.
17. (k) Chênevert, R.; Ziarani, G. M.; Dasser, M. Heterocycles 1999, 51, 593.
18. For enantioselective syntheses of indolizidine 209D, see: (a) Åhman, J.; Somfai, P. Tetrahedron Lett. 1995, 36, 303. Åhman, J.; Somfai, P. Tetrahedron 1995, 51, 9747.
19. For enantioselective syntheses of indolizidine 209D, see: (a) Åhman, J.; Somfai, P. Tetrahedron Lett. 1995, 36, 303. Åhman, J.; Somfai, P. Tetrahedron 1995, 51, 9747.
20. (b) Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem. 1995, 60, 398.
21. (c) Jefford, C. W.; Sienkiewicz, K. Thornton, S. R. Helv. Chim. Acta 1995, 78, 1511.
22. (d) Takahata, H.; Kubota, M.; Ihara, K.; Okamoto, N.; Momose, T.; Azer, N.; Eldefrawi, A. T.; Eldefrawi, M. E. Tetrahedron: Asymmetry 1998, 9, 3289. See also refs 5a, 5d, and 5g.
23. These indolizidine alkaloids 167B and 209D were detected once as a very minor trace components in unidentified dendrobatid frogs found in a single population [(a) Daly, J. W. Fortschr. Chem. Org. Naturst. 1982, 41, 205.
24. (b) Aronstam, R. S.; Daly, J. W.; Spande, T. F.; Narayanan, T. K.; Albuquerque, E. X. Neurochem. Res. 1986, 11, 1227]. Their structures have been tentatively assigned as 3 and 4 on the basis of mass spectral evidence whereas their absolute configurations were simply inferred as 5R,9R by analogy to the structurally related indolizidine 223AB whose absolute stereochemistry is known.