The 1,3-Dipolar Cycloaddition Reaction of 7,14-Dioxa-1-azadispiro[4.2.5.2]pentadec-1-ene 1-Oxide Derivatives with N-Phenylmaleimide. An Attempt to Synthesize Azasugar Analogues of Showdomycine

Abstract

7,14-Dioxa-1-azadispiro[4.2.5.2]pentadec-1-ene 1-oxide derivatives (1) undergo 1,3-dipolar cycloaddition reaction with N-phenylmaleimide (2) giving the corresponding isoxazolidines (3); attempts to convert 3 into the showdomycine azasugar analogues A and B failed.

References

1. J. J. Tufariello, in 1,3-Dipolar Cycloaddition Chemistry, ed. A. Padwa, Wiley, New York, 1984, vol. 2, pp. 135–161.
2. K. B. G. Torsell, in Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis-Novel Strategies in Synthesis, VCH, Weinheim, 1988, ch. 3 and 5.
3. For the synthesis of the azasugar analogue of showdomycine see G. Just and G. P. Donnini, Can. J. Chem., 1977, 55, 2998.
4. M. Koszytkowska-Stawińska, W. Sas and A. Sowińska, J. Chem. Res. (S), 1996, 162.
5. M. Burdisso, R. Gandolfi, P. Grünanger and A. Rastelli, J. Org. Chem., 1990, 55, 3427.
6. H. G. Aurich, G. Frenzen and M. G. Rohr, Tetrahedron, 1994, 50, 7417.
7. R. Grigg, M. Hadjisoteriou, P. Kennewell, J. Markandu and M. Thornton-Pett, J. Chem. Soc., Chem. Commun., 1993, 1340.
8. S. Cicchi, A. Goti, A. Brandi, A. Guarna and F. De Sarlo, Tetrahedron Lett., 1990, 31, 3351.