A New Strategy for the Synthesis of Selectively Protected Spermidine and Norspermidine Derivatives

Synlett

Volumn 1996, Issue 1, 1996, Pages 75-78

  Lemaire Audoire, Sandrine ^a   Savignac, Monique ^a   Genêt, Jean Pierre ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002993894     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5321     Document Type: Article

References (39)

1. For some leading references see : a) Bachrach, U. Function of Naturally Occuring Polyamines; Academic Press : New-York, 1973; b) Bachrach, U.; Kaye, A.; Chayen, R. Advances in Polyamines Research; Raven Press : New-York, 1983; c) Heby, O. Differentiation 1981, 19, 1-20; d) Morgan, D.M.L. Biochem. J. 1992, 286, 413-417.
2. For some leading references see : a) Bachrach, U. Function of Naturally Occuring Polyamines; Academic Press : New-York, 1973; b) Bachrach, U.; Kaye, A.; Chayen, R. Advances in Polyamines Research; Raven Press : New-York, 1983; c) Heby, O. Differentiation 1981, 19, 1-20; d) Morgan, D.M.L. Biochem. J. 1992, 286, 413-417.
3. For some leading references see : a) Bachrach, U. Function of Naturally Occuring Polyamines; Academic Press : New-York, 1973; b) Bachrach, U.; Kaye, A.; Chayen, R. Advances in Polyamines Research; Raven Press : New-York, 1983; c) Heby, O. Differentiation 1981, 19, 1-20; d) Morgan, D.M.L. Biochem. J. 1992, 286, 413-417.
4. For some leading references see : a) Bachrach, U. Function of Naturally Occuring Polyamines; Academic Press : New-York, 1973; b) Bachrach, U.; Kaye, A.; Chayen, R. Advances in Polyamines Research; Raven Press : New-York, 1983; c) Heby, O. Differentiation 1981, 19, 1-20; d) Morgan, D.M.L. Biochem. J. 1992, 286, 413-417.
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28. a) Genêt, J.P.; Blart, E.; Savignac, M.; Lemeune, S.; Lemaire-Audoire, S. Paris, J.M.; Bernard, J.M. Tetrahedron 1993, 50, 497-503;
29. b) European patent NoEP566459 (Rhône-Poulenc Chimie);
30. c) Genêt, J.P.; Blart, E.; Savignac, M.; Lemaire-Audoire, S.; Bernard, J.M. Synlett 1993, 9, 681-683;
31. d) Lemaire-Audoire, S.; Blart, E.; Savignac, M.; Pourcelot, G.; Genêt, J.P. Tetrahedron Lett. 1994, 35, 8783-8786;
32. e) French patent NoFR2703687 (Rhône-Poulenc Chimie).
33. a) Lemaire-Audoire, S.; Savignac, M.; Genêt, J.P. Tetrahedron Lett. 1995, 36, 1267-1270;
34. b) International patent NoWO9424088 (Rhône-Poulenc Chimie);
35. c) Lemaire-Audoire, S.; Savignac, M.; Dupuis, C.; Genêt, J.P. Bull. Soc. Chim. Fr. 1995, in print.
36. These reagents are prepared in two steps from 3-aminopropan-1-ol and 4-aminobutan-1-ol by conversion of the amine to the corresponding allyl, benzyl, tertiobutyl or trichloroethyl carbamates (90 to 100% yield) followed by quantitative mesylation of the alcohol. See : a) Green, T.W.; Wults, P.G.M. "Protective groups in Organic Chemisiry" Wiley Interscience, New-York 1991, p. 117 and 315; b) Fürst, A.; Koller, F.; Helv. Chim. Acta 1947, 30, 1454.
37. These reagents are prepared in two steps from 3-aminopropan-1-ol and 4-aminobutan-1-ol by conversion of the amine to the corresponding allyl, benzyl, tertiobutyl or trichloroethyl carbamates (90 to 100% yield) followed by quantitative mesylation of the alcohol. See : a) Green, T.W.; Wults, P.G.M. "Protective groups in Organic Chemisiry" Wiley Interscience, New-York 1991, p. 117 and 315; b) Fürst, A.; Koller, F.; Helv. Chim. Acta 1947, 30, 1454.
38. The same reaction carried out in the presence of the corresponding bromide derivatives gave lower yields (50-60%). Moreover, when mesylates were used without sodium iodide, the reaction was uncomplete even after prolonged time at reflux.
39. 13C NMR spectra were recorded on a Bruker AC 200 instrument at 50 MHz.