1632066-27-3Relevant academic research and scientific papers
New synthetic approach to C5-hydroxymethyl-substituted polyhydroxylated pyrrolizidines
Be?adiková, Daniela,Medvecky, Michal,Filipová, Alexandra,Monco?, Ján,Gembicky, Milan,Prónayová, Na?a,Fischer, Robert
, p. 1616 - 1620 (2014)
A new approach to C5-hydroxymethyl-substituted pyrrolizidines involving 1,3-dipolar cycloaddition of a d-mannose-derived cyclic nitrone and the S N-reaction of a silyl ketene acetal is presented. The synthesis shows good stereoselectivity as a result of the presence of a dioxolane substituent at C5 of the nitrone, the bulkiness of the silyl ketene acetal, and the shape of the pyrrolizidinylium intermediate formed during intramolecular reductive amination. This approach provides access to pyrrolizidines with the same relative configuration as that found in hyacinthacines C2 and C 3, and in (+)-pochonicine.Georg Thieme Verlag Stuttgart. New York.
