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Synthèses d'analogues contraints de céramides et de galactosylcéramides

Abstract : KRN7000 anti-tumor activity is due to immune system stimulation. It acts on autoimmunes diseases, bacterial and parasitic infections. Hence is needed the development of more selective analogues. The aim of this thesis is to form original constrained analogues of ceramides, KRN7000 derivatives precursors in restraining the conformation between the fatty chains to modulate the immune response Th1 or Th2. The synthetic approach is based on a heterocycloaddition [4+2] reaction between a chiral N-vinyl-1,3-oxazolidin-2-one and a heterodiene, both bearing one fatty chain. In all cases, the major formed cycloadduct is endo with Eu(fod)3 whereas with SnCl4, it is endo . Various analogues of ceramides have been prepared via a reactions cascade: hydroboration/oxidation, chiral auxillary removal, formation of the desired lactone then lactame. A final glycosylation will allow having access to galactosyl analogues.
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Cong Sau Vu. Synthèses d'analogues contraints de céramides et de galactosylcéramides. Autre. Université du Maine, 2011. Français. ⟨NNT : 2011LEMA1002⟩. ⟨tel-00675391⟩

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