Synthesis of trans-5-substituted-indolizidin-3-one

Synlett

Volumn , Issue 12, 1997, Pages 1359-1360

  McAlonan, H ^a   Stevenson, P J ^a   Thompson, N ^a   Treacy, A B ^a  

^a QUEEN'S UNIVERSITY BELFAST   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001868536     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1052     Document Type: Article

References (26)

1. Daly, J.W.; Garraffo, H.M.; Spande, T.F. In Alkaloids, New York 1993, 43, 185.
2. Raub, M.F.; Cardellina, J.H.; Spande, T.F. Tetrahedron Lett. 1992, 33, 2257.
3. Garraffo, H.M.; Spande, T.F.; Daly, J.W.; Baldessara, A.; Gros, E.G. J. Nat. Prod. 1993, 56, 357.
4. Daly, J.W.; Nishizawa, Y.; Edwards, M.W.; Waters, J.A.; Aronstam, R.S. Neurochem. Res. 1991, 16, 489.
5. a. Methods for preparing 5-substituted-cis indolizidines Chiral 2° alcohols and epoxides as precursors. Takahata, H.; Bandoh, H.; Momose, T. Heterocycles 1996, 42, 39.
6. Machinaga, N.; Kibayashi, C. J. Org. Chem. 1992, 57, 5178.
7. b. Chiral Glutamic acid precursors: Thanh, G.V.; Celerier, J.P.; Lhommet, G. Tetrahedron-Asymmetry 1996, 7, 2211.
8. Jefford, C.W.; Sienkiewicz, K.; Thornton, S.R. Helv. Chim. Acta, 1995, 78, 1511.
9. c. Diels Alder N-Acylnitroso: Kibayashi, C.; Aoyagi, S. Synlett, 1995, 873.
10. d. Dipolar Cycloadditions: Bourdin, B.; Collins, I., Nadin, Holmes, A.B.; Long, M.E.; Man, J.; Baker, R.A. J. Chem. Soc. Perkin 1 1994, 2205.
11. e. Enaminones: Paulvannan, K.; Stille, J.R. J. Org. Chem. 1994, 59, 1613.
12. Michael, J.P.; Gravestock, D. Synlett. 1996, 981.
13. f. Photochemical: Momose, T.; Toshima, M.; Toyooka, N.; Hirai, Y.; Eugster, C.H. J. Chem. Soc. Perkin 1 1997, 1315.
14. Muraoka, O.; Okumura, K.; Maeda, T.; Tanabe, G.; Momose, T. Tetrahedron Asymmetry, 1994, 5, 317. Methods for preparing 5-trans and/or cis 5-substituted indolizidines.
15. g. Chiral 2,3-Dihydro-4-pyridones as precursors: Comins, D.L.; Zhang, Y. J. Amer. Chem. Soc. 1996, 118, 12248.
16. h. Diels Alder iminium ion: Pilli, R.; Dias, L.C.; Maldaner, A.U. J. Org. Chem., 1995, 60, 717.
17. i. Radical: Lee, E.; Li, K.S.; Lim, J.H. Tetrahedron Lett., 1996, 37, 1445.
18. Beckwith, A.L.J.; Joseph, S.P.; Mayadunne, R.T.A. J. Org. Chem. 1993, 58, 4198.
19. j. CN(R,S) Strategy: Yue, C.; Nicolay, J.; Royer, J.; Husson, H. Tetrahedron 1994, 50, 3139.
20. Katoh, T.; Nagata, Y.; Kobayashi, Y.; Arai, K.; Minami, J.; Tereshima, S. Tetrahedron 1994, 50, 6221.
21. Although sodium borohydride is known to reduce pyroglutamic esters, the reason for this is taken to be activation of the ester by the electronegative nitrogen on the α-carbon. Undoubtedly this is a factor, but the results of this reduction study indicate that other factors are at play in these systems. Silverman, R.B.; Levy, M.A. J. Org. Chem. 1980, 45, 815.
22. Beak, P.; Zajdel, W.J. J. Amer. Chem. Soc. 1984, 106, 1010.
23. Beak, P.; Lee, W.K. J. Org. Chem. 1993, 58, 1109.
24. Hart, D.J. J. Amer. Chem. Soc. 1980, 102, 397.
25. Johnston, F. Chem. Rev. 1968, 68, 375.
26. Hoffmann, R.W. Chem. Rev. 1989, 89, 1841.